travel to cuba from key west

Mark Watson

California-based member of a LA Motorcycle Club and a keen traveler. Author of bestselling books on Amazon about Route 66, Alaska Highway, PCH 1 & Overseas Higwhay. 🇺🇸

Ultimate Guide to Traveling from Key West to Cuba

Dreaming of a Caribbean getaway with a dash of old-world char m? Look no further than Cuba! Located just a stone’s throw away from the southernmost point of the United States lies the vibrant island nation of Cuba. And what better way to embark on this unforgettable adventure than from the enchanting shores of Key West? In this guide, we’ll delve into everything you need to know to make your journey from Key West to Cuba a seamless and memorable experience.

Can you visit Cuba from Key West?

Yes, you can visit Cuba from Key West, and there are two main ways to do so:

• Book a boat trip from Key West to Cuba: Some tour operators offer boat trips or cruises from Key West to Cuba. These trips can provide a unique and adventurous way to travel between the two destinations, allowing travelers to experience the journey by sea. However, it’s important to note that travel by boat to Cuba from the United States may be subject to regulations and restrictions, so it’s essential to check with the tour operator and relevant authorities for the most up-to-date information on requirements and permissions.
• Fly from Key West International Airport to Cuba: Another option is to fly from Key West International Airport to Cuba. While direct commercial flights between Key West and Cuba may not be common, there are occasional charter flights or scheduled flights operating between the two destinations. Additionally, there are organized trips and travel agencies in Key West that arrange tours and packages for travelers interested in visiting Cuba. These organized trips typically handle transportation, accommodations, and itinerary planning, making it easier for travelers to navigate the process of visiting Cuba from Key West.

How long is boat ride from Key West to Cuba?

The duration of a boat ride from Key West to Cuba can vary depending on several factors , including the specific departure and arrival points in Key West and Cuba, the type of boat used, weather conditions, and the route taken.

Generally, the distance between Key West and Cuba is approximately 90 miles (145 kilometers) at its closest point, which is between Key West and Havana. A fast boat or ferry could potentially make the journey in around 3 to 5 hours under optimal conditions. However, it’s essential to consider that travel by boat can be influenced by weather conditions, maritime regulations, and other factors, which may affect the duration of the trip.

If you’re considering a boat trip from K ey West to Cuba, it’s advisable to check with tour operators or boat charter companies for more precise information on the duration of the journey and any other relevant details. Additionally, make sure to inquire about any necessary permits, documentation, or regulations for traveling by boat between the United States and Cuba.

Can you enter Cuba as a tourist?

Yes, you can enter Cuba as a tourist . Cuba is a popular tourist destination known for its vibrant culture, beautiful beaches, historic architecture, and more. However, it’s important to note that travel to Cuba as a tourist from the United States was subject to certain restrictions and regulations imposed by the U.S. government.

Travelers from other countries may have different requirements for visiting Cuba , so it’s essential to check the specific entry requirements based on your nationality before planning your trip. Additionally, it’s advisable to stay informed about any updates or changes to travel regulations and restrictions related to Cuba before your visit.

Key West to Cuba Day Trip to Havana

Taking a day trip from Key West to Havana, Cuba , is an exciting adventure, offering a glimpse into Cuba’s vibrant culture and history. While such day trips were not common due to the distance and logistics involved, it’s essential to note that options may vary over time. Here’s a hypothetical itinerary for a day trip from Key West to Havana:

Morning: Departure from Key West

• 6:00 AM: Arrive at Key West International Airport or designated departure point for the day trip.
• 6:30 AM: Board a chartered flight or boat for the journey to Havana.

Mid-Morning: Arrival in Havana

• 9:00 AM: Arrive in Havana, Cuba. 9:30 AM: Clear immigration and customs procedures.
• 10:00 AM: Begin guided tour of Havana.

Daytime Activities in Havana

• 10:30 AM – 12:30 PM: Explore Old Havana, including historic landmarks such as Plaza de la Catedral, Plaza Vieja, and the Malecón.
• 12:30 PM – 1:30 PM: Enjoy a traditional Cuban lunch at a local restaurant, experiencing authentic Cuban cuisine.
• 1:30 PM – 3:30 PM: Continue the guided tour, visiting iconic sites such as El Capitolio, Revolution Square, and the Museum of the Revolution.
• 3:30 PM – 4:30 PM: Leisure time for shopping, exploring local markets, or enjoying a coffee at a Havana cafe.

Late Afternoon: Departure from Havana

• 4:30 PM: Return to the airport or designated departure point. 5:00 PM: Board the return flight or boat to Key West.

Evening: Return to Key West

• 7:30 PM: Arrive back in Key West.
• 8:00 PM: End of the day trip.

Please note that this itinerary is purely hypothetical and may not reflect actual travel options or schedules. Additionally, travelers should verify current travel restrictions, entry requirements, and transportation options before planning a day trip from Key West to Havana, as regulations and availability may vary.

Exploring the Idea

Embarking on a trip from Key West to Cuba is like stepping into a time capsule, transporting you to a land where vintage cars roam the streets, colorful buildings line the cobblestone roads, and the rhythm of salsa fills the air. The allure of Cuba lies in its rich history, diverse culture, and stunning landscapes, making it a bucket-list destination for travelers around the globe.

How to get from Key West to Cuba

While direct commercial flights from the United States to Cuba are limited, traveling from Key West offers a convenient alternative. One of the most popular ways to reach Cuba from Key West is by ferry . Several ferry companies operate daily services between Key West and Havana, offering travelers a scenic journey across the Florida Straits. Be sure to book your tickets in advance to secure your spot on the ferry.

Another option for reaching Cuba from Key West is by private boat or yac ht. This option allows for greater flexibility in terms of travel schedule and itinerary, giving you the freedom to explore different parts of Cuba at your own pace. However, it’s essential to familiarize yourself with the necessary paperwork and regulations for traveling to Cuba by private vessel, including obtaining the required visas and permits.

Visa and Documentation to Cuba

Before setting sail for Cuba, it’s crucial to ensure you have all the necessary documentation in order. American citizens are required to obtain a visa to travel to Cuba, which can be obtained through the Cuban Embassy or consulate in the United States. Additionally, travelers must adhere to the regulations outlined by the U.S. Department of the Treasury’s Office of Foreign Assets Control (OFAC) regarding travel to Cuba, including the purpose of your visit and spending limitations.

Exploring Cuba

Once you’ve arrived in Cuba, get ready to immerse yourself in a world of endless discovery. From the bustling streets of Havana to the pristine beaches of Varadero, Cuba offers a diverse array of attractions and experiences for every type of traveler. Explore the historic neighborhoods of Old Havana, where centuries-old architecture blends seamlessly with vibrant street art and lively cafes. Indulge in the rich flavors of Cuban cuisine, from mouthwatering ropa vieja to refreshing mojitos made with locally grown mint.

Beyond the capital city, venture into the lush countryside of Viñales, where tobacco fields stretch as far as the eye can see and limestone cliffs rise dramatically from the earth. Take a leisurely stroll along the Malecón in Trinidad, where pastel-colored buildings overlook the sparkling waters of the Caribbean Sea. Whether you’re a history buff, nature lover, or simply seeking relaxation, Cuba offers something for everyone.

Embarking on a journey from Key West to Cuba is not just a trip; it’s an adventure of a lifetime. From the moment you set foot on the ferry or sail away on a private yacht, you’ll be captivated by the beauty, charm, and warmth of this enchanting island nation. So pack your bags, grab your passport, and get ready to discover the magic of Cuba, just a short journey away from the shores of Key West.

Check out my other blog post on day trips from Key West here: Day Trips from Key West – 10 Best Places to visit!

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Explore the finest attractions along the Overseas Highway and Florida Keys with my travel guide, ‘Florida Keys Overseas Highway Travel Guide – 101 Best Stops,’ now available on Amazon. This comprehensive guide is your ultimate companion for those seeking adventure and wonder along THE OVERSEAS HIGHWAY & FLORIDA KEYS! Discover 101 amazing places with convenient ‘Scan QR and go’ functionality for easy navigation.

Mark Watson is a California-based member of a Los Angeles motorcycle club and an avid traveler. He has completed seven full journeys along the iconic Pacific Coast Highway on his Harley-Davidson and is passionate about promoting this historic drive to others. Mark has also explored the Alaska Highway and Route 66, and has authored four bestselling travel guides on Amazon: “Route 66 Travel Guide – 202 Amazing Places,” “Alaska Highway Travel Guide – 202 Best Stops,”, “Pacific Coast Highway Travel Guide – 202 Best Stops”, and “Florida Keys Overseas Highway Travel Guide – 101 Best Stops.”

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Key West to Cuba Day Trip to Havana!

Havana Has Never Been Easier

Only 90 miles from Key West (50-minute flight).

Spend the day in Havana and return to Key West in time for your dinner reservation.

Join our guided groups as we explore the cultural and historical connections between Cuba & Key West, while supporting the Cuban people’s newfound entrepreneurial spirit.

View Itinerary

Havana Day Trip FAQ

OurKeyWest has been on the Island since 1974. Our Portfolio of Premium Guest Activities presents the highest quality experiences in Key West. All the best activities have limited availability, so make sure to book your fun well in advance. OurKeyWest is local and available to assist you every day from 8am-6pm, or by visiting the OKW Galleria & Welcome Lounge at 613 Simonton St. in Old Town Key West. #MoreFun

Havana Trip Details

• $1195 per person (All Inclusive).
• Available Tuesdays  & Fridays.
• Must reserve at least 48 hours in advance.
• Valid passport required.
• Limited Availability. Book well in advance.
• Small group, guided Hemingway Literary Excursion.

What’s Included

• Visa & all required documentation
• Transportation & guide in Cuba
• Entry to all museums & points of interest
• All US & Cuban government taxes  
• Lunch & drinks

This Trip is Seriously Fun! We’re already planning to do it again this year -Theresa Somebody

TALES FROM HAVANA

• Traveling To Havana Cuba

So, you’ve finally decided to see what this magical and supposedly forbidden tropical island is all about. Interestingly, you’ve decided to look past the smoke screen that is 60+ years of anti-Cuba American foriegn policy. Fact is, as Americans, we’re allowed to travel just about anywhere we’d like, it’s just that elements of our federal […]

Stories from Cuba

• Paths to Freedom
• Last Flight Out
• Cuban Art & Artists of Havana

Havana Itinerary

7:00am – Check-in at Key West Airport

8:00am – 50 Minute Flight to Havana

9:00am – Clear Customs and start your Havana adventure

9:30am – Your Havana Excursion begins with a trip to Ernest Hemingway’s home in Cuba known as Finca Vigía in San Francisco de Paula Ward in Havana, Cuba. Both Finca Vigía and Hemingway’s Key West home are now museums. You will see Hemingway’s famous fishing boat named El Pilar.

12:00pm – Lunch at an authentic Cuban restaurant. 

1:30 pm: After lunch, you will head to Old Havana for a walking tour. Our Old Havana walking tour brings the city to life, allowing you to be swept up in all that this vibrant city has to offer. The city offers an unrivaled sensory experience that you will always remember! You will walk the sun-drenched cobblestone streets as you take in the oldest square in Havana (Plaza de Armas), which includes the oldest cathedral in the Western Hemisphere. Next, we follow in the footsteps of American literary icon Ernest Hemingway, making 3 stops that were Hemingway favorites: La Bodeguita (cafe), the Ambos Mundos (Hotel), & El Floridita Bar (the birthplace of the Daiquiri). 

5:00pm – Return to the Havana Airport.

7:00pm – Arrive back in Key West.

• Price: $1195 per person. This includes airfare, visas, ground transportation in Cuba, local guide (meets you at airport), all taxes, tour & entry fees.
• Day trips leave on Tuesdays and Fridays.
• Trips must be reserved at least 48 hours in advance.
• A copy of your passport will be required to obtain a visa.
• ESTA VISA holders are not eligible for travel to Cuba from the USA, and would not be able to go on the Havana Day Trip. Standard VISA holders are eligible for travel.
• Small group, all-day guided tour.
• Havana Day Trips use a small, Key West based aircraft which carries less than 10 passengers. In Havana, the tour uses private ground transportation.  

In partnership with Air Key West, OurKeyWest develops and markets Cuban Cultural & Educational Experiences with the aim of supporting the Cuban people by providing technical business assistance to Cuban entrepreneurs and by creating a market to which Private Cuban Citizens can sell their goods and services. Our efforts are intended to promote independent activity and strengthen civil society in Cuba, as our guests maintain a full-time educational schedule that includes meaningful interaction with Cuban individuals.

*US Customs does not allow cigars and alcohol to be brought back from Cuba.

*ESTA VISA holders are not eligible for travel to Cuba from the USA, and would not be able to go on the Havana Day Trip. Standard VISA holders are eligible for travel.

Cancelation Policy:

Cancelations and rebookings incur a 15% cancelation/rebooking fee. Cancelations must be confirmed at least 7 days prior to departure to receive a partial refund. Cancelations confirmed less than 7 days prior to departure will not receive a refund.

You may reschedule your Havana Day Trip excursion for a future date within 12 months from your initial booking date.

NO-SHOWS WILL BE CHARGED THE FULL EXCURSION FARE. Please be on-time for your scheduled trip. Check in is required at 7:00 am. Late arrivals are subject to cancelation without refund.

Online Booking Cancelation: Online bookings are charged a booking fee by Fareharbor Reservation System. When canceling an Online Booking, the booking fee portion is non-refundable. 

Operator Cancelation: cancelations due to weather or maintenance or other unforeseen circumstances are at the sole discretion of the pilot & airline for your safety. If the operator cancels the flight, you will be given the option to reschedule your trip or receive a refund of the ticket price. You may reschedule your Havana Day Trip excursion for a future date within 12 months from your initial booking date.

The Havana Day Trip requires a minimum of 4 paying passengers to embark, if the airline does not have the required minimum number of passengers, the flight will be canceled, and you will be given the option to reschedule your trip or receive a refund of the ticket price. You may reschedule your Havana Day Trip excursion for a future date within 12 months from your initial booking date.

Local since 1974, we facilitate authentic and compelling guest experiences emphasizing the natural world, art, music, food, history, and local characters. We provide premium concierge services, and serve as market-maker for a select pre-screened portfolio of the island’s best guest activity providers. We have a commitment to quality and manage a full-service local concierge call center providing personal guest support from 8am to 8pm every day.

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Day Trips From Key West To Cuba

Last Updated By VacationIdea Staff on February 11, 2024

If you’re planning a day trip to Cuba from Key West, the first step is to actually look at how you’re going to get there. You have two basic options: travel by air or travel by sea. The latter is by far the simplest option for now, but we’ll cover both of them below.

Getting To Cuba From Key West By Air

If you can afford it, however, it is possible to arrange charter or private flights over to Cuba direct from Key West. These flights aren’t cheap, but they’re exceptionally fast and the whole journey can be done in less than an hour. Some travel companies and tour operators like Our Key West are starting to provide new ways for travelers to get to Cuba from Key West, so this possibility might become more accessible as time goes by.

Getting To Cuba From Key West By Sea

Ferries from Florida to Cuba will be running from multiple ports and cities, including Miami and Fort Lauderdale, but Key West will represent the fastest option, with the entire journey able to be done in around four hours. As soon as these ferries become available, booking your spot on board will be the best option to get to Cuba from Key West.

Things To Do In Cuba

- Castillo de la Real Fuerza - Head out to the east of Havana to stop off at Castillo de la Real Fuerza, a 16th century star-shaped fort. It looks out over the harbor, offering some stunning views to visitors, and is nicely located near the ferry terminals, as well as some great bars and restaurants too. There's a lot of history behind this place, and it's a popular spot for families to discover.

• 1. Overview
• 2. Getting To Cuba From Key West By Air
• 3. Getting To Cuba From Key West By Sea
• 4. Things To Do In Cuba

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Key West Uncovered: Your Passport to Paradise!

How To Get To Cuba From Key West

Imagine being just a short boat ride away from the vibrant and culture-rich island of Cuba, all while starting your journey from the stunning coastal city of Key West. In this article, we will explore the various ways you can make your way from Key West to Cuba, offering you tips and guidance on how to embark on this exciting adventure. So, if you’re ready to discover the enchanting charm of Cuba from the convenience of Key West, let’s dive into the details and get you on your way!

Table of Contents

Commercial Flights

To travel to Cuba from Key West, one option is to take a commercial flight. Several airlines now offer direct flights from Key West International Airport (EYW) to Havana’s Jose Marti International Airport (HAV) and Varadero’s Juan Gualberto Gomez Airport (VRA). These flights provide a convenient and time-efficient way to reach Cuba, with flight durations typically ranging from just over an hour to two hours.

Charter Flights

Another option for traveling from Key West to Cuba is to take a charter flight. Charter flights are operated by private companies and offer more flexibility in terms of departure dates and times. These flights may also provide a more personalized experience, as they usually accommodate a smaller number of passengers. However, it’s important to note that charter flights may be more expensive than commercial flights and may require advance booking.

Ferry Services

If you prefer a scenic journey, you can opt to travel to Cuba by sea. Currently, there are ferry services available from Key West to Havana. These services offer a unique experience, allowing you to enjoy the breathtaking views of the ocean during your journey. However, it’s important to check the availability and schedules of ferry services, as they may vary depending on the season and weather conditions.

Private Boats

For those who own a private boat or have access to one, traveling to Cuba by sea can be an exciting option. This allows you to have more control over your travel itinerary and enjoy the freedom of exploring the Cuban coastline at your own pace. However, it’s crucial to research and comply with all the necessary regulations and requirements for private boaters entering Cuba.

Travel Regulations

Visas and entry requirements.

Before traveling to Cuba, it’s essential to understand the visa and entry requirements. U.S. citizens must have a valid passport and a Cuban tourist visa, also known as a “tourist card,” to enter the country. These tourist cards can be obtained through Cuban consulates or from authorized travel agencies. It’s important to plan ahead and ensure that you have all the necessary documents before your trip.

Tourist Cards

To obtain a Cuban tourist card, you will need to provide certain information, including your personal details and the purpose of your visit. The tourist card is usually valid for a specified period, typically 30 days, and can be extended if necessary. It’s important to note that the Cuban tourist card is not a substitute for a visa, so it’s crucial to check the specific requirements based on your nationality before traveling.

Authorized Travel Categories

In addition to the visa and tourist card requirements, U.S. citizens must comply with the travel regulations set by the U.S. Department of the Treasury’s Office of Foreign Assets Control (OFAC). These regulations currently permit certain categories of authorized travel to Cuba, such as family visits, educational activities, professional research, and humanitarian projects. It’s important to determine which category applies to your travel plans and ensure that you meet the necessary criteria.

Key West to Havana Options

Non-stop flights.

For travelers looking for the most direct and time-efficient option, non-stop flights from Key West to Havana are available. These flights enable you to reach Havana without any layovers or connections, providing a streamlined travel experience. Non-stop flights are typically offered by commercial airlines and are popular among those who prioritize convenience and wish to minimize travel time.

Connecting Flights

If you’re flexible with your travel schedule and looking for more flight options, connecting flights from Key West to Havana are worth considering. These flights involve a layover or connection at another airport before reaching Havana. While connecting flights may add some travel time, they often provide more flexibility in terms of departure dates, times, and potential cost savings.

Key West to Varadero Options

Similar to the Havana route, non-stop flights are also available from Key West to Varadero. Varadero’s Juan Gualberto Gomez Airport is a popular tourist destination known for its stunning beaches and resorts. Non-stop flights offer a direct route to Varadero, eliminating the need for layovers or connections and allowing travelers to start their beach vacation as soon as they arrive.

For those who prefer a wider range of flight options, connecting flights from Key West to Varadero are available as well. These flights may involve a layover or connection at another airport before reaching Varadero. Connecting flights provide more flexibility in terms of departure dates, times, and potential cost savings. They can be a great option for budget-conscious travelers or those looking to explore additional destinations during their journey.

Key West to Other Cuban Cities Options

While non-stop flights from Key West to other Cuban cities may be limited, there are still connecting flight options available. These flights usually require a layover or connection at a major airport in Cuba, such as Havana or Varadero, before reaching your final destination. It’s important to check the flight schedules and availability, as well as any visa or entry requirements specific to the city you plan to visit.

Navigating Cuban Airports

Jose marti international airport (hav).

Jose Marti International Airport (HAV) is the main international airport in Cuba and serves as the gateway to the country for many travelers. Located in Havana, this airport offers a range of amenities and services, including currency exchange, duty-free shops, restaurants, and transportation options. It’s important to allocate sufficient time for immigration and customs procedures upon arrival and departure, as well as to familiarize yourself with the airport layout to ensure a smooth travel experience.

Juan Gualberto Gomez Airport (VRA)

Juan Gualberto Gomez Airport (VRA) is the primary airport serving Varadero and the surrounding resort areas. This airport welcomes a large number of international tourists, particularly those visiting the famous Varadero beaches. Similar to Jose Marti International Airport, VRA offers various facilities and services to cater to travelers’ needs. It’s advisable to arrive early and allow ample time for immigration, customs, and baggage claim procedures.

Other Major Airports

In addition to Jose Marti International Airport and Juan Gualberto Gomez Airport, there are other major airports in Cuba that cater to domestic and international flights. These include airports in cities like Santiago de Cuba, Holguin, and Santa Clara. Although non-stop flights from Key West to these cities may be limited, connecting flights may be available, allowing you to reach your desired destination with ease.

Booking Accommodations

Cuba offers a range of hotel options to suit different preferences and budgets. From luxury resorts to budget-friendly accommodations, there is something for everyone. Many international hotel chains have established a presence in major Cuban cities, providing high-quality amenities and services. It’s advisable to book accommodations in advance, especially during peak travel seasons, to secure the best rates and availability.

Casas Particulares

For a more authentic and personalized experience, consider staying in a casa particular. These are private homes that rent out rooms or apartments to travelers. Staying in a casa particular allows you to immerse yourself in the local culture and interact with Cuban families. These accommodations often provide a warm and welcoming environment, offering a unique insight into everyday life in Cuba. It’s recommended to research and book casas particulares in advance, ensuring a comfortable and enjoyable stay.

Online Booking Platforms

To simplify the accommodation booking process, various online platforms allow travelers to search and secure accommodations in Cuba. Websites and apps such as Airbnb, Booking.com, and Expedia offer a wide range of options, allowing you to browse through different properties, read reviews, and make reservations conveniently. These platforms often provide detailed information about the accommodations, including photos, amenities, and pricing.

Exploring Cuba

Must-visit destinations.

Cuba is a country rich in history, culture, and natural beauty. From the vibrant streets of Havana to the colonial charm of Trinidad and the stunning beaches of Varadero, there are countless destinations to discover. Other notable places to visit include Viñales, known for its picturesque tobacco fields, and Santiago de Cuba, famous for its Afro-Cuban music and dance. It’s recommended to plan your itinerary in advance and allocate sufficient time to explore the diverse attractions Cuba has to offer.

Transportation within Cuba

Getting around Cuba can be done through various means of transportation. Taxis, both privately-owned and state-owned, are readily available in major cities and tourist areas. Classic American cars, known as “yank tanks,” offer a nostalgic and unique mode of transportation, particularly in Havana. Additionally, there are Viazul buses that provide affordable and comfortable intercity travel. For shorter distances or when exploring smaller towns, bicycle rentals and horse-drawn carriages can be charming options.

Cuban Currency

Cuba has its own currency system, with two separate currencies in circulation: the Cuban Convertible Peso (CUC) and the Cuban Peso (CUP). The CUC is primarily used by tourists and is pegged to the U.S. dollar, while the CUP is the currency used by locals. It’s important to familiarize yourself with the currency exchange rates and have an understanding of the different denominations to ensure smooth transactions. It’s advisable to carry cash in Cuba, as credit and debit cards may have limited acceptance.

The official language of Cuba is Spanish. While English is spoken and understood in tourist areas, it’s helpful to learn a few basic phrases in Spanish to communicate with locals. Cubans are generally friendly and appreciate the effort to speak their language. Additionally, having a pocket-sized Spanish phrasebook can be useful when traveling to more remote areas where English may be less commonly spoken.

Returning to Key West

Departure process.

When departing Cuba and returning to Key West, it’s important to allow sufficient time for check-in, security procedures, and immigration. Depending on the airport and flight, arrival at the airport at least two to three hours before the scheduled departure time is typically recommended. It’s advisable to arrive early to avoid any potential delays and ensure a stress-free departure.

Customs and Immigration

Upon arrival in Key West, U.S. citizens will need to pass through customs and immigration. It’s essential to have all the necessary documentation ready, including your passport and any customs forms provided during your flight. Be prepared to answer questions about your trip and declare any goods or items you are bringing back from Cuba. It’s important to comply with all customs and immigration regulations to avoid any potential issues.

Souvenirs and Cuban Goods

Bringing back souvenirs and Cuban goods from your trip is a common practice. However, it’s important to familiarize yourself with the U.S. customs regulations regarding the importation of Cuban products. Certain restrictions and limitations may apply, particularly on items such as cigars and rum. It’s recommended to check the latest guidelines from the U.S. Customs and Border Protection agency to ensure compliance with the regulations.

In conclusion, whether you choose to travel to Cuba from Key West by air or sea, understanding the necessary travel regulations, booking accommodations in advance, and preparing for the unique experiences and opportunities Cuba offers will contribute to a memorable and enjoyable journey. From exploring the vibrant streets of Havana to relaxing on the beautiful beaches of Varadero, Cuba has something to offer every traveler. Plan your trip, immerse yourself in the rich culture, and create unforgettable moments on this Caribbean island.

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3471 S. Roosevelt Blvd. Key West, FL 33040 Phone (main): (305) 923-4033 Phone (Havana Day Trips): (305) 290-3563 Phone (after-hours / urgent mobile): (305) 923-4034 Email: [email protected]

Havana day trips, yes, legal day trips to cuba are again available.

Air Key West operates in full compliance with the new stricter US regulations announced 4 June 2019.

Our excursions fall under OFAC’s “ Support for the Cuban People” guidelines by assisting and sponsoring Cuban entrepreneurs and their privately-owned and privately-run businesses to the maximum extent possible.

Our Havana Day Trip Ernest Hemingway excursion explores and educates travelers on the cultural and historical connections and close ties between Key West and Havana, Cuba.

Scheduled trips are available Tuesdays and Fridays  (eventually increasing back to four days per week).

Your day in Havana:

7:15 AM: Check in at Key West International Airport (KEYW). 8:00 AM: Flight departs Key West. 9:00 AM: Arrive at Jose Marti International Airport (MUHA) in Havana, Cuba where you meet your guide and driver. 9:30 AM: Depart MUHA and travel to “Finca Vigia”, Ernest Hemingway’s house and now museum. View Key West-registered boat “Pilar”. 11:30 AM: Visit the fishing village of Cojimar, where Hemingway would depart on fishing expeditions. 12:00 PM: Lunch at a “paladar” (privately-owned restaurant) in Cojimar. 1:30 PM: Visit Old Town Havana Hemingway literary landmarks including:

• “Ambos Mundos” hotel, where Hemingway frequented and whose room is maintained as a free museum.
• “La Bodeguita del Medio” restaurant and bar favored by many writers and poets, including Hemingway.
• “La Floridita” restaurant and bar that claims to be the birth place of the daiquiri, Hemingway’s favorite drink.
• Shop for crafts directly from local vendors at a local market.

4:00 PM: Meet driver at “Parque Central” for return to MUHA. 5:00 PM: Flight departs MUHA. 6:00 PM: Arrive at KEYW.

$1,195 per person

• Visa & all required documentation
• Transportation & guide in Cuba
• Entry to all museums & points of interest
• Lunch & drinks
• All US & Cuban government taxes  

Requires booking no later than 12:00 PM the day prior and a valid passport.

For additional information, or to book via the phone, call (305) 290-3563

Key West Rebecca

(305) 304-8910

[email protected], day trip to havana.

Tour Havana Cuba

Yes, legal Day Trips to Cuba are again available! Fly round trip from Key West to Havana all in one day.  Our excursions fall under OFAC’s  “ Support for the Cuban People”  guidelines by assisting and sponsoring Cuban entrepreneurs and their privately-owned and privately-run businesses to the maximum extent possible.

Our Havana Day Trip Ernest Hemingway excursion explores and educates travelers on the cultural and historical connections and close ties between Key West and Havana, Cuba.

Scheduled trips are available  Tuesdays and Fridays  (eventually increasing back to four days per week).

7:15 AM: Check in at Key West International Airport (KEYW). 8:00 AM: Flight departs Key West. 9:00 AM: Arrive at Jose Marti International Airport (MUHA) in Havana, Cuba where you meet your guide and driver. 9:30 AM: Depart MUHA and travel to “Finca Vigia”, Ernest Hemingway’s house and now museum. View Key West-registered boat “Pilar”. 11:30 AM: Visit the fishing village of Cojimar, where Hemingway would depart on fishing expeditions. 12:00 PM: Lunch at a “paladar” (privately-owned restaurant) in Cojimar. 1:30 PM: Visit Old Town Havana Hemingway literary landmarks including:

“Ambos Mundos” hotel, where Hemingway frequented and whose room is maintained as a free museum.

“La Bodeguita del Medio” restaurant and bar favored by many writers and poets, including Hemingway.

“La Floridita” restaurant and bar that claims to be the birth place of the daiquiri, Hemingway’s favorite drink.

Shop for crafts directly from local vendors at a local market.

4:00 PM: Meet driver at “Parque Central” for return to MUHA. 5:00 PM: Flight departs MUHA. 6:00 PM: Arrive at KEYW.

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FAQs - booking Cuba flights

How does kayak find such low prices on flights from key west to cuba.

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Key West to Cuba.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Cuba?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Cuba from Key West is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Key West to Cuba?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Cuba with an airline and back to Key West with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Cuba?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Cuba from Key West up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Key West - Cuba Flights

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Private charters to cuba.

CHARTER YOUR DREAM BOAT AND EXPERIENCE THE ADVENTURE OF A LIFETIME

Just 90 miles away and yet a world apart, Cuba awaits those daring enough to explore its colorful streets and fascinating culture. At Havana Fleet, we make planning the perfect journey easy with our range of options, from single-day round trips to extended voyages with certified captains and crew. For more immediate gratification, choose our state-of-the-art power yachts for a day trip through the plazas of Havana that’ll have you back in the U.S before nightfall. Or if you prefer something longer, take advantage of our luxury Cuba experience onboard the Havana Moon. Have the time to explore Matanzas, Santiago de Cuba, Cienfuegos, and other culturally rich ports around the island. With Havana Fleet’s knowledgeable team behind you – your Cuban dream getaway is just one call away! Don’t miss this fantastic opportunity – contact us today to plan your Cuba adventure!

Our professional captains and crews at Havana Fleet are here to provide an unforgettable experience. Explore Cuba’s vibrant culture and unique history with a luxurious power yacht charter from Key West. Discover why Cuba is called “The Pearl of the Antilles” – get in touch today!

Contact us for more information about charters to Cuba.

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Key West to Havana Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Key West to Havana offer the perfect respite. Not only does exploring Havana provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Key West to Havana may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Havana are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Havana more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Havana is now!

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* Please be advised, as of right now the U.S Government requires U.S citizens to have special permission to visit Cuba.  Any and all U.S charters to Cuba must be approved by the U.S Government prior.

Info About Cuba Charters

Directly across the Straights of Florida from Key West lies the island of Cuba. Only 90 miles away, yet a million miles from any country you’ve ever visited. Call Key West Charter Boat or fill out a quote form. We’ll introduce you to several travel options for journeying Cuba, from single-day round trips to excursions lasting a week or longer. Or if you prefer, fill out a quote form. Either way, Charter Boat to Cuba is an experience you don’t want to miss.

State-of-the-art power yachts from Key West to Cuba allow you to spend a day wandering through plazas of Havana and be back in the United States by nightfall. For a more leisurely voyage, employ the professional services of a certified captain and sail to Cuba on a 65-foot catamaran, making stops at Matanzas, Santiago de Cuba, Cienfuegos and other culturally rich ports around the island.

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Cuban History & Island Info

Circumnavigating Cuba has been popular since Christopher Columbus first set foot here in 1492. The famous explorer liked the tropical paradise so much, he claimed it in the name of Spain. Five centuries later, Ernest Hemingway felt the same, planting his flag and living in the outskirts of Havana for over twenty years.

On a Key West to Cuba charter boat trip, you can discover the island’s colorful history for yourself. No place in the world has quite the same blend of cultures and traditions. You’ll appreciate why Cuba’s nickname, Pearl of the Antilles, is a particularly accurate moniker. Being on Duval street is nice by why not have an authentic Cuban experience instead?

Cubas Untouched Beauty

Fortunately, Cuba still has much of the extraordinary raw beauty Columbus so appreciated— endless pristine beaches of pure white sand, sparkling turquoise waters, verdant, rugged mountains. Guided excursions into the interior can be arranged on the spur of the moment locally or planned in advance by Key West Charter Boat.

The food alone is justification enough to visit this island nation of eleven-million people. In addition to the exceptional regional fare, be sure to order the national dish of Cuba, ropa vieja. Local adaptations aside, ropa vieja is made of shredded flank steak in an aromatic tomato sauce base, served with black beans, yellow rice, plantains, and fried yuca—nearly always accompanied by beer.

The gastronomic masterpiece is both delicious and affordable, costing approximately nine Cuban pesos ($9.00 U.S. dollars) per serving. No wonder so many people return to Cuba year after year for vacation.

Ernest Hemingways Secret Retreat

Hemingway journeyed to Cuba for several reasons, not least of which was the world-class fishing. The warm waters of the Gulf Stream flow the entire length of the island’s north side, attracting spectacular Sailfish, Black Fin Tuna , Mahi Mahi, Wahoo, and a diverse assortment of other sport fish.

Key West Charter Boat can put you in the fighting chair of a sport fishing yacht trolling Cuban waters in a matter of a few hours. Surprisingly, Key West to Cuba distance is substantially shorter than Miami’s proximity to the Bahamas. Journey to the southern coast of this internationally acclaimed fishing destination and you’ll be in the Caribbean Sea, where the daily catch could easily include mammoth Tiger and Hammerhead sharks.

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Cuban culture.

No Key West to Cuba trip would be complete without spending at least a day in Havana. Once a playground for the rich and famous, Hollywood starlets and business tycoons were found here nightly, gambling in casinos and taking in a show at the world-famous Tropicana Nightclub. Havana in the 1950s was an “anything goes” town of fame and occasional infamy. Today the high life has disappeared, old-world charm lingers.

Stroll the streets of Old Havana and you’ll feel a mixture of cultural influences that are uniquely Cuban, from the conservative architecture of a Spanish cathedral to plazas lined with brightly colored building facades. Stop along the way and sample some of the city’s famous street food, including Tostones—deep-fried plantains served with a variety of dipping sauces.

Any walk through Old Havana is sure to pass under clotheslines strung between apartment buildings and have an encounter with at least one vintage 1950s-era Ford or Chevy automobile, still in operational condition and often used as taxis.

The Richness Of Cuban Culture

In Cuba, music feels like it’s a religion of its own, as sacred and loved. Some of the finest musicians you’ll ever hear can be found playing in places like Plaza Vieja and Plaza de Armas. So do what the locals do: sit, enjoy a cup of Cuban coffee, and partake in a little people watching.

Whether you travel from Key West to Cuba on a Hemingway excursion, fishing expedition, or simply to tour and experience a magnificent jewel of the Caribbean, you’ll discover Cuban citizens to be welcoming and engaging. For additional information about Key West to Cuba trips, either by sea or day trips by Air Key West , call Key West Charter Boat today.

Our Cuba Charter was absolutely stunning, to say the least.   We took our boat all over Cuba, visited fabulous beaches & explored local villages. Amazing.

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If you want to experience something like no other, charter a boat to Cuba.  Our trip to the island was like a step back in time, not to mention beautiful.

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Can You See Cuba From Key West? (Mystery Solved!)

You might find yourself on the soft andy beaches of Key West and wondering what you can see from across the distance? Is it just more open water or is there something more exciting out there?

Many have wondered if they could see the alluring life of Cuba from North America but it is a bit of a mystery as to whether that’s true. 

Now, instead of you hopping on a flight or packing up the car to see for yourself, we’ll answer the question for you. We do, however, recommend visiting Key West. It is a fantastic trip.

We have the details right here in this article. We’ll let you know if you can see Cuba from Key West and any essentials you may need for the discovery.

Where Is Key West?

You can find Key West located in Southwestern Florida. It is located at the of the Florida Keys which are a chain of small, coral islands extended from the southern tip of Florida. 

Key West, Florida is the southernmost point of the United States. This can make it seem difficult to travel to. On the contrary the island can be reached by land, air and sea. 

Simply drive along the US1 Highway or the Overseas High that connects Key West to mainland Florida.

The 160 mile drive from Miami is considered to be one of the most breathtaking and unique driving experiences the US has to offer.

The stunning turquoise waters whilst driving out to sea make this experience otherworldly no matter how many times you do it. 

Or you can get a short flight from Miami, Ft.Lauderdale, Tampa or Orlando to save time on your journey. Watch as the waters open up beneath you and take it all in. 

Traditionally, many prefer to travel by sea with the daily ferry services provided. Breathe in the fresh sea air and take in the sights and sounds of the ocean as you travel to the island. 

How To See Cuba From Key West

If you are trying to see Cuba all the way from Key West, Florida there are a few factors you will need to consider: 

Weather 

There can under no circumstances be a foggy, rainy, or generally gloomy sky. Please bid your view of the horizon a fond farewell if you visited Key West during the wet season.

It is crucial to ensure that the weather is bleak and clear if you have any chance of seeing the Cuban horizon.

You’ll need to pick the right time of day to see the desired Cuban view. Right before sunset is the perfect time to trial the idea of seeing Cuba from Key West. 

Instruments

Using your natural site might not get you very far during your exploits. In order to have a slight chance at seeing Cuba a telescope or a pair of binoculars will be required. 

With being only 90 miles south of Key West and if you happen to have a high-powered telescope, you might find yourself in luck! Otherwise you might experience some difficulties in coming out successful. 

Despite all of this, it should be noted that numerous attempts to see the fabled Cuban view from Key West have fallen short.

So none of the aforementioned actions provide a guarantee for the Cuban viewpoint. But that shouldn’t take away from the fun in trying!

Can You Travel From Key West To Cuba?

Of course! Like any form of long distance travel , the easiest way to get to Cuba from Key West is flying. 

Now, this will involve hiring a private or charter flight to take directly to Cuba from Key West. You can travel the 90 miles in less than hours and spend the day or week in Cuba before returning.

But this can be rather expensive and not generally attainable by everyone. 

So what are your other options? While you might not be out purchasing your own private flight to the Cuban Island, flying is still possible.

You would have to fly to Miami and then fly to Cuba. This can be time consuming and still come to a hefty sum. 

Or, the simplest method is by sea. There are multiple ways to travel by sea especially with companies such as Havana Ferry Partners and Cuba Ferries.

You can find a direct service from Key West to Cuba that will take around 4 hours. Make sure to book your seats on this epic journey across the sea to Cuba as soon as possible!

Driving to Cuba From Key West

While 90 miles may not seem like a large distance to cover, driving across the dividing water filled with sharks and other creatures is not recommended.

Not to mention that cars aren’t exactly made to be driven in water. 

But, an amazing group of people were creative enough to make it happen. Building a ‘Floating Truck’ which successfully carried them across the water from Key West to Cuba. 

Not exactly the trip you were looking to take the kids on now is it? 

However, traveling from Florida (Key West) to Cuba necessitates extreme preparations and efforts, none of which a typical traveler would choose to undertake.

In the end, even if you are able to create a magical hydraulic land vehicle, the Cuban government’s legislative prohibitions on sailing ships should cause you to reconsider your options.

Swimming to Cuba From Key West 

So driving isn’t the best option and you might fancy yourself as a decently strong swimmer. One dip in these Arctic Ice waters will have you reconsidering.

Known as the ‘shark attack capital of the world’ swimming in these waters isn’t something you should have on your bucket list. 

However, that’s not to say the journey hasn’t been done. In 2013, a 64 year old woman swam for 53 hours straight without the protection of a shark cage, and saw herself in Cuba.

Impressive but not exactly the easiest or safest way to see Cuba. 

This may seem like a fun, once in a lifetime exhibition but it is most definitely worth avoiding.

These sharks aren’t playing around and our bodies just aren’t made for the less than warm conditions of the water. 

So, Can You See Cuba From Key West?

In short, no you cannot see Cuba from Key West. Or any part of Florida for that matter. 

You might be partial to believing that climbing to the top of the Key West lighthouse would increase your odds. But it wont.

The naked simply cannot see the glorious lands of Cuba from Key West. Even with the help of telescopes and binoculars it’s not likely that you’ll be successful. 

You’re chances falling even more if you’re on ground level. 

Don’t believe us? Head down to Key West and find out for yourself! Enjoy the sites in Key West and try your luck at capturing the enticing lands of Cuba.

Don’t forget to check the weather forecast for your best chances. 

Your best bet at seeing Cuba is to simply catch a flight and soak in the culture and traditions of these history rich lands.

Or take your chances at hiring a water car and attempt to drive your way onto Cuban Lands. 

• Recent Posts

• What Is The Largest Island In Cuba? - September 19, 2022
• Havana – Why Is It Cuba’s Most Exciting City? - September 19, 2022
• Cheapest Time To Visit Cuba (Ultimate Guide) - September 19, 2022

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Cheap flights from Key West to Cuba from $496

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Prices for flights from Key West Airport to Cuba refresh daily.

How old do you have to be to fly from Key West Airport to Cuba?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Key West Airport to Cuba.

What documentation or ID do you need to fly to Cuba?

The travel and health documents you'll need for your trip to Cuba may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cuba. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Alternative routes for Key West to Cuba

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times, similar key west to cuba flights, flexible with your destination broaden your search and find flights similar to your key west to cuba route, flights from key west to:, flights from key west to caribbean, other flights from key west, flights to cuba from:, flights to cuba from florida, flights to cuba from united states, other flights to cuba, why use momondo, why should i use momondo to find a flight deal from key west to cuba.

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Key West to Cuba for you.

Can I find flights from Key West to Cuba with flexible booking policies on momondo?

Yes. All flights to Cuba from Key West on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Key West to Cuba?

momondo helps you find the best flight between Key West and Cuba by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Key West to Cuba right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Key West to Cuba flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Cuba trip

We make it super easy to schedule, organize and travel with friends or family. trips is free — and available to use no matter where you book., big names and deals, filter for what you want, trusted and free, price alerts, find better results for your stay in cuba, complete your trip to cuba, get notified when prices go down, daily price changes in your inbox - only with price alerts..

A Concise Measurement Guide: Distance Between Key West and Cuba

Distance Between Key West and Cuba

The distance between Key West and Cuba is a topic that has intrigued many people, myself included. As an expert blogger, I’ll provide you with some valuable information to satisfy your curiosity.

Located in the southernmost part of Florida, Key West is just 90 miles away from the shores of Cuba. This proximity has played a significant role in shaping the culture and history of Key West, as well as fostering a strong connection between these two places.

The short distance between Key West and Cuba has made it possible for adventurous individuals to embark on exciting journeys across the Straits of Florida. Whether by boat or even swimming, some brave souls have attempted this challenging feat, seeking to bridge the gap between these neighboring lands.

While there are legal restrictions and regulations regarding travel between Key West and Cuba, the geographical closeness serves as a constant reminder of the shared heritage and enduring ties that exist between these vibrant destinations.

Understanding the Geographic Location of Key West and Cuba

Let’s delve into the fascinating geographic location of Key West and Cuba. These two destinations are situated in close proximity, yet each possesses its own distinct characteristics. Here’s a breakdown of their locations and what sets them apart:

• Distance between Key West and Cuba: Key West, a vibrant island city, is located at the southernmost tip of the United States in Florida. It sits approximately 90 miles (145 kilometers) north of Cuba, making it the closest point in mainland U.S. to our neighboring island nation.
• Strategic Positioning: Due to its strategic position at the entrance of the Gulf of Mexico, Key West has historically played a significant role as a gateway to both the Caribbean Sea and Latin America. Its proximity to Cuba has influenced various aspects such as culture, trade, and tourism over time.
• Climate Variations: While both Key West and Cuba experience tropical climates with warm temperatures year-round, there are subtle variations due to their differing geographical features. Key West benefits from cool ocean breezes that moderate its climate while being shielded by larger landmasses from severe weather events like hurricanes compared to Cuba.
• Unique Landscapes: Key West boasts picturesque beaches with white sand and crystal-clear turquoise waters that attract tourists from around the world seeking relaxation or water activities such as snorkeling or diving amidst vibrant coral reefs. In contrast, Cuba offers diverse landscapes encompassing lush rainforests, majestic mountains like Sierra Maestra, tobacco fields in Vinales Valley, charming colonial architecture in Havana, stunning beaches like Varadero, and much more.
• Cultural Influences: The geographical closeness between Key West and Cuba has fostered cultural exchanges throughout history. Cuban influences can be seen in various aspects of Key West’s architecture, cuisine (such as Cuban sandwiches), music (like salsa), art (with hints of Afro-Cuban styles), and festivals (such as the annual Cuban-American Heritage Festival).

In summary, Key West and Cuba share a unique geographical connection that has shaped their histories, cultures, and interactions. While Key West offers a tropical paradise with its own distinct charm, it’s impossible to overlook the impact of Cuba’s proximity on this vibrant city.

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Amey, an intrepid traveler and avid blogger, roams the world, absorbing diverse cultures, flavors, and experiences. Her writing captures the essence of her adventures, inspiring others to explore. Amey's infectious passion for travel and storytelling epitomizes a life filled with exploration and adventure.

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Your Guide to a Florida Keys Road Trip: Key Largo to Key West

Posted: March 12, 2024 | Last updated: March 13, 2024

Your road trip guide to the Florida Keys

One of the best state road trips in America has to be the sun-kissed drive from Key Largo to Key West in the Florida Keys. This road, known as the Florida Keys Overseas Highway, takes you through a 125-mile island chain that begins just south of Miami. It hopscotches over 42 bridges and five islands, and has turquoise waters stretching in every direction into the Atlantic Ocean, Florida Bay and Gulf of Mexico.

So if you're looking for the perfect Atlantic Coast road trip or cheap beach vacation , look no further than this road trip guide from Key Largo to Key West. And if you'd rather travel from Key West to Key Largo, rest easy—the route works either way. There are shuttles that run from Key Largo to Key West, but keep in mind, you'd be missing out on all the fun in between.

By the way, once you embark on the Florida Keys Overseas Highway, you'll notice that many sites along the way use mile markers (MM) in their address. We use those mile marker points in this story to help you navigate the drive.

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Mile marker: 108–90

The first of the Florida Keys you'll hit after driving about an hour south from Miami en route from Key Largo to Key West is, well, Key Largo. Often referred to as the Dive Capital of the World, Key Largo includes one must-see stop: John Pennekamp Coral Reef State Park (MM 102.5), the first underwater preserve in the United States.

Experienced and novice snorkelers and SCUBA divers will be enthralled by the teeming marine life that lives just below the water's surface, like parrot fish, barracudas and sea turtles. More experienced divers enjoy exploring the USS Spiegel Grove, one of the largest ships ever intentionally sunk to create an artificial reef where pretty fish can thrive.

Back on dry land, travelers can wander nearly six miles of trails at Dagny Johnson Key Largo Hammock Botanical State Park, home to more than 80 species of plants and animals. You can also peruse the work of local artists at myriad galleries.

Best beach: Cannon Beach, found within John Pennekamp Coral Reef State Park, has shallow waters that are perfect for wading. You may even spot cannons and anchors on the beach that remain from a 1715 Spanish shipwreck.

Where to eat: Dig into the catch of the day at The Fish House, Key Largo Conch House or Snook's Bayside Restaurant & Grand Tiki Bar, some of the best traditional restaurants in the area. If you'd rather turf than surf, check out Jimmy Johnson's Big Chill.

Where to stay: If you can't get enough of the underwater world, stay at Jules' Undersea Lodge , the world's first underwater hotel. If you'd rather keep dry, try the adults-only Bungalows Key Largo .

Mile marker: 90–63

Next up en route from Key Largo to Key West is the fisherman's paradise known as Islamorada. Considered the Sport Fishing Capital of the World, it's where backcountry sport fishing and saltwater fly-fishing got their start. Countless seasoned boat captains are ready for hire to take you out to catch the wahoo, marlin, mahi-mahi and tuna that swim in these waters.

There's an even quirkier way to interact with fish here: hand-feeding the tarpon off the docks of Robbie's Marina (MM 77.5). Since 1976, countless Keys visitors have stopped to feed them, and more than 100 kinds of fish gather at the docks for their daily snacks. Feeding the fishies there is so popular, it's been named the No. 1 activity in all the Florida Keys.

Islamorada is also a terrific spot to kitesurf, stand-up paddleboard, go for a hike or take a bicycle ride. Stop by the Laura Quinn Wild Bird Sanctuary, where injured or displaced birdies now make their homes. Or visit the History of Diving Museum, which boasts one of the world's largest collections of diving helmets.

Best beach: Anne's Beach is popular with families (and dogs) because of its shallow waters and lack of waves. Take a walk along the boardwalk or enjoy a picnic at one of the covered tables.

Where to eat: For a quintessential casual Florida Keys meal, go to the Hungry Tarpon. If you want more elegant fare, make reservations at Chef Michael's for creatively inspired local dishes.

Where to stay: When it's time to lay your head for the night, check in to one of the new oceanfront suites at Cheeca Lodge & Spa , or your own cottage at The Moorings Village & Spa .

Mile marker: 63–40

Marathon is the island chain's top boating destination—and for good reason. The area boasts nearly 2,400 boat slips and plenty of facilities to accommodate sailors passing through. But you don't need your own boat to enjoy Marathon and its waters.

For a truly different experience, hop on over to Cruisin' Tikis and have a floating tiki bar adventure. Sunset, mangrove and harbor cruises are all available, as is a swim-stop cruise for a chance to jump into the water.

While you're here, you should also visit Pigeon Key, an island that is accessible by boat, trolley or walking the 2.2-mile Old Seven Mile Bridge. It has a museum to explore, either on a guided tour or on your own. The Bridge is open for walking, running, bicycling, rollerblading and, of course, watching the killer sunrises and sunsets.

Best beach: Sombrero Beach is one of the prettiest beaches in the Florida Keys—not to mention one of the best beaches in Florida . And it's not just popular with humans; sea turtles nest here between April and October.

Where to eat: For any meal, stop by Castaway, which has been serving guests for more than 70 years. Or make a night of it at Hide Away Café, which has an extensive wine list.

Where to stay: The Faro Blanco Resort & Yacht Club is set on the waterfront and gives you a taste of marina life. Lime Tree Bay Resort on Long Key has spacious townhomes for rent.

The Lower Keys

Mile marker: 40–4

After crossing the Old Seven Mile Bridge out of Marathon, you'll find yourself in the Lower Keys, where natural habitats and wildlife refuges thrive. It's no wonder this part of the Florida Keys is known as the Natural Keys. You might even want to consider taking an electric vehicle on this road trip so you don't disturb the animals.

Your best chance to spot a native Key deer, a subspecies of the Virginia white-tailed deer that somehow made its way south, may be in the National Key Deer Refuge, comprised of 9,200 acres stretching from Bahia Honda Key to Sugarloaf Key on the edge of the Gulf of Mexico. More than 20 endangered and threatened plant and animal species can be found within the refuge. Take a quiet walk at dusk or dawn for your best chance to glimpse a Key deer, or join a ranger-led tour to learn more about the area.

Aside from all the eco-friendly fun, Stock Island is well worth a stop. Their maritime history goes back generations, and the marina is filled with shrimping and fishing boats. Artists have been flocking to Stock Island, too, and share their works in galleries dotted across the small island.

Best beach: The shallow, clear water and white sand at Calusa Beach make it a locals' favorite. The beach is a perfect spot for snorkeling too.

Where to eat: In addition to the freshest of seafood, Big Pine Rooster serves up ribs and a special-recipe meatloaf. Or sip like the locals at No Name Pub, located on Big Pine Key.

Where to stay: Consider the waterfront Sugarloaf Lodge , stay in an Airstream at Big Pine Key Resort  or pop a tent on one of the reserved campsites at Bahia Honda State Park.

Mile marker: 4–0

You've made it to the end! Closer to Cuba than Miami, Key West is known for its nightly sunset celebrations, party atmosphere and laissez-faire vibe, but it's really so much more.

If you're a writer or bookworm, you'll certainly want to make plans to visit the Ernest Hemingway Home & Museum, where you should keep an eye out for the famous six-toed cats. Then wander through Key West's Bahama Village, a 12-block area of historic homes and restaurants.

Consider a day trip to Dry Tortugas National Park, about 70 miles west of Key West in the Gulf of Mexico, where you'll find some hidden gems . The island, accessible by boat or seaplane, is popular for snorkeling and feeling like you're on your own private island, not to mention touring the Civil War–era fort.

Best beach: Fort Zachary Taylor Beach—or Fort Zach, as locals call it—predates the Civil War and boasts the island's very best sandy stretch.

Where to eat: No visit to Key West is complete without a meal at Blue Heaven, where you can dine with wandering roosters for breakfast, lunch and dinner. Or snag a spot on the tiny balcony at Santiago's Bodega for tapas and flowing wine.

Where to stay: The boutique Gardens Hotel , the adults-only Kimpton Hotels Ridley House  or the new Capitana Key West , to name a few. Wherever you stay, you're sure to find your place in Key West, and it's likely you'll follow so many others' lead and start planning your return visit before you even leave.

Art and history in the Florida Keys

Road-tripping from Key Largo to Key West, it's easy to appreciate all the natural beauty. That said, the Keys aren't just a terrific destination for eco-travelers, but artists and history buffs too.

It's easy for artists to find inspiration throughout the Florida Keys. Fortunately for road-trippers, there are many spots to stop and admire their work. One of the largest artists' communities in the Florida Keys is Stock Island in the Lower Keys, just about three miles from the commercial area of Key West. What was once a shrimping boat marina is now a blend of fishermen and painters, sculptors and other artisans who have created an energetic and supportive community.

For history buffs, in addition to Pigeon Key in Marathon and the Civil War–era Fort Jefferson in Dry Tortugas National Park, other must-stops in Key West include the Audubon House & Tropical Gardens, Harry S. Truman Little White House and the Southernmost Point in the continental United States.

Planning your Florida Keys road trip

Now that you're inspired to hit the road, it's time to start planning. After budgeting for a road trip , your next step is to decide whether you will travel south from Key Largo to Key West, or north from Key West to Key Largo. Or maybe you'll opt for a roundtrip.

If you're starting off in Key Largo, it's important to note that the Florida Keys Overseas Highway begins at the Miami-Dade/Monroe County line. So if you're flying to Florida, Miami International Airport (MIA) is the way to go. If you begin in Key West, the airport (EYW) is on the island.

If you're already driving one of the best road trip cars to get to Florida, you're all set. But if you need a loaner, choose one of the best cars to rent for a road trip . Consider packing these road trip essentials and download some of the best podcasts for road trips to make the miles fly by.

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