jimmy buffett tours key west

Jimmy Buffett Tour Walking Tour In Key West

Insider Pricing

Expert guides, daily tours, verified tour provider.

You will begin this 1hour and 30 minute guided tour by meeting your tour guide, (who will be wearing a neon green shirt) at Margaritaville (500 Duval Street). Musician Jimmy Buffett arrived in Key West 50 years ago in 1971. This walking tour will take you to the locations around Old Key West that inspired his songs, where he played his first gig, some of his favorite watering holes, places he ate, bars he played in, his recording studio, the first and the current location of Margaritaville, Mallory Square, and end at Capt. Tony’s Saloon.

What to expect:

• Learn incredible facts about the life and times of Jimmy Buffett and Key West from knowledgeable tour guides.
• Enjoy a slice of Key Lime pie, water, and alcoholic beverage.
• This walking tour is moderately paced and suitable for most fitness levels.

What to bring:

• Key West can be hot, so please bring some water, sunscreen and a hat.
• Wear comfortable clothing and shoes for walking.
• Our walking tours will take place rain or shine. Ponchos are provided if necessary.

What To Bring

Restrictions, cancellation policy.

Jimmy Buffet Tours Near Me (Key West)

All you need to bring is your excitement. Dress appropriately and your camera, you do not want to miss out on capturing these memories.

An adult must accompany people under 18. This tour is for ages 12 and up.

Customers have the ability to cancel the trip with a full refund up to 48 hours prior to the tour.

Jimmy Buffet Tour Reviews

Don't take our word for it.

This tour has been hand selected & verified to be a top tier provider

Best haunted ghost tour in Key West! Loved seeing Robert the doll.

Just what we were looking for! We loved the whole experience! AMAZING GHOST TOUR

Family of 5

This tour was perfect 👌  Amazing guide & entire team! Highly Recommend!

Key West Travelers

Leave a comment cancel reply.

Save my name, email, and website in this browser for the next time I comment.

By using this form you agree with the storage and handling of your data by this website. *

Default title

Demo Description

This will close in 0 seconds

HEMINGWAY IN KEY WEST TOURS

Voted "Best Walking Tours" in 2023

Experience one of our authentic tours of the sights and sounds frequented by famed author Ernest Hemingway or Jimmy Buffett in old Key West.

Hemingway Food & Walking Tour 

Start Time:   9 :00  am

Jimmy Buffett

Start Time: 10:00 am

 Hemingway

Start Time: 7:00 pm

Jimmy Buffett thrills locals in a rare Key West homecoming

The man who made a fortune singing Margaritaville is thrilling his Key West fanbase — including some who knew him back when he landed here more than 50 years ago — with an extended visit back to the island.

Jimmy Buffett and the Coral Reefer Band will launch their Second Wind tour in Key West on Thursday, Feb. 9 and Saturday, Feb. 11 at the city's amphitheater. But the band played two surprise shows downtown on Saturday and Monday.

The arena star certainly built his multi-million-dollar brand out of Key West lore — hangovers and flip flops included. But aside from popup and private shows, Buffett, 76, rarely plays here. In 2011, he did a Duval Street show that drew a mass of fans.

In the intimate show Saturday night at the Key West Theater, Buffett treated the crowd of largely locals to an emotional retelling of his Key West story. He was a "nobody from nowhere," when he arrived in 1971.

The Key West he once knew was a dusty old funky beach town . It was long before the city pivoted to tourism, which today is its economic engine.

Buffett's story is one shared by many here: wash up at the end of the road without a plan or money, and wind out building a new life.

Even without the shared millions, Key West transplants like Buffett know the feeling of landing at Mile Marker 0 while on a losing streak and finding a safe haven from the mainland.

For the first act, he and his band played his first Key West-inspired record, A White Sport Coat And A Pink Crustacean, from 1973. Buffett saved the party anthems — Fins , Volcano , and yes, Margaritaville— which he wrote while stuck in traffic on the Seven Mile Bridge , for the second act.

"These days I'm up about the time I used to go to bed," Buffett said, recalling the old days when the Full Moon Saloon in Key West, the Conch Flyer bar at the airport and the Boca Chica Bar on Stock Island were considered a real pub crawl by long- time residents.

"It was like Columbus crossing the ocean, that's what we used to refer to it as," Buffett said, as a crowd laughed at the old saw about the chore of leaving Key West p roper.

Buffett's media team declined an interview with WLR N, but locals have seen the star around town lately — riding his bike along Simonton Street and stopping in a Stock Island restaurant for a hogfish sandwich.

He name checked Key West legends, starting with Coffee Butler, who let a young Buffett open for him at local bars , and he dedicated the show to his friend Tom Corcoran the Florida writer who died in January.

As Buffett strummed the opening of his tribute to the sea, A Pirate Looks at 40, on Saturday night, he had a moment.

"It's so cool singing this song in Key West," Buffett said off the cuff and without missing a note, to cheers. He released the song in 1974.

On Thursday, Buffett will make his debut at the Coffee Butler Amphitheater at the Truman Waterfront Park.

H e had added the Fe b . 4 and 6 Key West Theater shows, after locals fumed over Ticketmaster 's policies and and pricing. Tickets were $99 plus some fees.

For these surprise shows Buffett's team went old-school: People had to line up outside the Eaton Street theater until tickets went on sale at noon. Two per person, with ID required .

The ticket line, which started for a few fans before sunrise Feb. 3, lined a block between Eaton and Fleming streets. And, in Key West style, it turned into an impromptu street party.

#showday pic.twitter.com/yslTsNQSrW — Jimmy Buffett (@jimmybuffett) February 4, 2023

Orderly and cheerful, fans chatted and caught up under a bright sun. Some had chairs and snacks to share, including rum cake, hand delivered from another local who runs a rum distillery.

Those whose luck ran out at the box office window weren't happy, but they were reminded over the hours by the promoter's staff they were risking walking away empty-handed.

Those who scored were also applauded by their pals.

"This is why people come to Key West now," said Sally Crane, a local who showed up at 6:30 a.m. Feb. 3 to stand in line and succeeded. "They just want to hang out, have fun with their friends. Kind of live this island lifestyle and that's what Jimmy Buffett represents." Copyright 2023 WLRN 91.3 FM. To see more, visit WLRN 91.3 FM .

Work in Paradise - Join our team! Check our current openings Here .

• Reservations
•   Order Now

Jimmy in Key West

A brief jimmy buffett biography.

Jimmy Buffett arrived in Key West in November 1971 with singer and songwriter Jerry Jeff Walker (already famous for "Mr. Bojangles") and Teresa "Murphy" Clark. Jerry Jeff, Murphy and her young son, Justin, had offered Jimmy refuge in their open-air Coconut Grove home after Jimmy fled Nashville's weather and business climate.

His marriage to his hometown sweetheart had ended, and he'd failed to find many open doors in the Music City. The record industry didn't understand the young man's style, motivation or lyrics. Murphy and Jerry Jeff wanted to deliver some happiness to dispel Jimmy's gloom and sense of loss. After a week or two of Florida-orientation, they piled into "Flying Lady," Jerry Jeff's elegant silver and maroon '47 Packard sedan, for a drive southward. Jimmy Buffett had never before seen the Florida Keys. Key West was an outpost over 100 miles from our mainland - closer to Cuba than to Florida - a place of fascinating history and charm, dependent upon the ocean for much of its income yet subject to the whims of weather and the perils of change. Jimmy's discovery of the island meant everything to the man.

It changed his life and countless other lives in turn. As time passes, that quick November 1971 jaunt to the Keys means more and more to the island, the state of Florida, and the national culture.

Read more about Jimmy Buffett  HERE .

THE OLD ANCHOR INN - "THE SNAKE PIT"

People slept in their cars behind the bar. The restrooms often flooded; you walked on bricks to keep your shoes dry. Men in clothes swiped from clotheslines gambled tens and twenties at the pool table. The picket fence lining the sidewalk was erected to appease the city; there had been too many complaints of saloon patrons falling out the front door. Murals on the insides of the window shutters were painted by Monkey Tom, swapped for a "bottomless" bar tab. Bud and Dorothy MacArthur's place at 208 Duval always was crowded - but more at three in the morning that at three in the afternoon. A blue cloud hung low, directly above the roof.

Many survivors of The Snake Pit recall wee-hours dance marathons and Joe Cocker singing "She Came in Through the Bathroom Window" 20 or 30 times a night. Speaking of the subject, there was a fine message crawled on the wall in the men's room: "Life and ink run out at the same time. - Squid" As we know the quote found its way to immortality.

There are more Anchor Inn stories that can't be told than ones that will be told. One evening, in 1972, Jimmy was fortunate to escape the bar's upstairs apartment and a woman gone crazy on Lower Duval. Curse words, a broken beer bottle and a hasty exit were reported. Several of Jimmy's most valued possessions escaped harm and possible theft. Indeed, that's one of the stories we don't tell.

THE CHART ROOM BAR

In November 1971, when Jimmy was brought for the first time to Key West by Jerry Jeff Walker and Teresa "Murphy" Clark, the trio's first stop in town was the Chart Room Bar at the Pier House Motel. The bartender on duty was Tom Corcoran, a friend of Jerry Jeff and today an author whose mystery novels are set in Key West and the Lower Keys. Tom gave Jimmy his first beer "on the house" as a welcome to the island. Jimmy saw the freebie and the bar's ambiance as omens of great things to come.

Jimmy began his tropical career playing for drinks in the The Chart Room for treasure divers, pot smugglers, beachcombers, politicians and friends. Some nights he was joined by Vaughn Cochran on washboard ( and today a well-known artist ), Steve Goodman (writer of Banana Republic and City of New Orleans), and even Jim Croce. Jimmy's earliest Key West related songs were tested on the Chart Room audience, and he sang a few that might surprise the die-hard fans: Tell Laura I Love Her was a frequent request, as were Danny's Song by Loggins & Messina, and the obscure, beautiful On My Own, written by B. W. Stevenson.

HOWIE'S LOUNGE

There's some debate about who'd been hired for the gigs, but most believe it was Jerry Jeff Walker. That didn't keep Jimmy from sharing the spotlight. And a single spot it was, with the stage being the ten square feet normally occupied by Coffee Butler's piano bench in the front window of Howie's Lounge at 109 Duval Street.

Howie employed only females, so the joint drew a willing crowd. The ten or twelve people who cared and knew what they were seeing fought for the barstools that bordered Coffee's grand piano.

They got to witness such spontaneous wonders as "Go-Jo," about Jimmy and Jerry Jeff having to rebuild the front suspension of a old Packard in order to travel down the Keys.

They pulled their lyrics out of smoky air (to which they returned). Memorable performances; too few, too short.

PETTICOAT III

Inventor-industrialist Foster Talge (the Rival Manufacturing Company - maker of Seal-a-Meal, Crock-Pot and electric can openers ) retired to Key West to fish as often as possible from his yacht, Petticoat III.

He hired Norman Wood, a local bank director, to be his captain. Norman loved deep sea fishing as much as Foster did, and his $175 weekly salary was more an object of false contention than payment for his skills and time.

Several men whom Norman had met in the Chart Room - including Rick Lutz and Jimmy Buffett - were hired as mates for the regular fishing trips.

One has to believe that their paychecks compared favorably to the captain's. The bonuses were tops: all the fresh fish they could eat.

Norman and Shirley Wood became loyal supporters of the new entertainer in town. Buffett relished the time he spent in the company of the Wood family. When his musician's income required a supplement, the First Mate job was always open. When the first pressing of A White Sport Coat and a Pink Crustacean arrived by air express, Jimmy took it directly to the Woods' living room for an island debut.

A LOT TO DRINK ABOUT

On any given Thursday night in Key West, the spirited staff from Margaritaville don their domestic caps and assume the laid-back lifestyle that our island is known for; walking the beach, applauding the sunset, lounging poolside or in my case, hoping to hell I don’t fall out of the hammock as I dose off….again.

But last Thursday was different, last Thursday was better, last Thursday the sun set a little slower, last Thursday Jimmy Buffett was in town.

We got the word on Wednesday and even though we were sworn to secrecy, by 8PM the following evening a throng of locals were choking the 500 block of Duval. I’m not sure how they all knew because I told my friends not to tell anyone. But no worries, this time there was a list, a VIP list I suppose you could say and we were all on it. This time Jimmy saw to it that the employees were in first, seated first, and had a drink in hand…first. Of course we had to pay for the drink(s) but being on the list is, at the risk of sounding cliché, priceless.

Jimmy had spent the week in CMA Musician of the Year Mac McAnally’s Muscle Shoals recording studio working on new songs. The current state of the country prompted our troubled troubadour to take pen in hand and put his spin on the state of the union, noting in particular that "we have a lot to drink about.” And since drinking was involved, what better place than Key West to premier the new song.

Key West’s current living legend embodies the spirit of our islands infamous forerunners in the guise of shipwreck salvors, road weary writers and bar owners; it’s safe to say that best-selling author Jimmy Buffett has certainly found treasure in Margaritaville. So he and Mac came into town on Lincoln’s Birthday to share the new song, spend some time with old friends and favor the Margaritaville crew with Key West classics, the songs we know by heart.

Tryin’ to reason with hurricane season while reminiscing over lost landmarks and cousins who’ve crossed over, Jimmy took us all on a nostalgia trip that I for one, at times, wish was one-way. The past is so pleasant, the memories so malleable, the beer is too cold the daiquiris too fruitiful….but I digress. Jimmy played the good old songs for over an hour, recorded a video of “We've Got A Lot To Drink About” that is probably already on YouTube, gave a heartfelt thanks to partners and supporters and then told the staff, “…you don’t have to go to work tomorrow!”

The economy is in a bad way, my 401(K) took a hit, and the ATM machine kept my card, but this is one night that I can truly say that it pays to work at Margaritaville. So despite Jimmy’s verbal permission slip and the protestations of the morning shift, Friday morning its bidness as usual. But in our case, usual is pretty special.

Jimmy Buffett Tour

• Visit historical locations
• A slice of Key Lime Pie and water
• Alcoholic Beverages
• 500 Duval St, Key West, FL 33040, USA Tour Guide (wearing a neon green shirt) will meet you on the sidewalk in front of Margaritaville
• Capt Tony’s Saloon, 428 Greene St, Key West, FL 33040, USA
• Not wheelchair accessible
• Service animals allowed
• Near public transportation
• Confirmation will be received at time of booking
• No heart problems or other serious medical conditions
• Travellers should have a moderate physical fitness level
• This experience requires good weather. If it’s cancelled due to poor weather, you’ll be offered a different date or a full refund
• This experience requires a minimum number of travellers. If it’s cancelled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
• This tour/activity will have a maximum of 15 travellers
• For a full refund, cancel at least 24 hours in advance of the start date of the experience.

Similar experiences

• You'll start at 500 Duval St 500 Duval St, Key West, FL 33040, USA Tour Guide (wearing a neon green shirt) will meet you on the sidewalk in front of Margaritaville See address & details
• 1 Key West Stop: 2 hours You will begin this 1 hour and 30 minute guided tour by meeting your tour guide, (who will be wearing a neon green shirt) at Margaritaville. Musician Jimmy Buffett arrived in Key West 50 years ago in 1971. This walking tour will take you to the locations around Old Key West that inspired his songs, where he played his first gig, some of his favorite watering holes, places he ate, bars he played in, and his recording studio. You will get to eat a slice of the best Key Lime Pie, before visiting the location of the first Margaritaville, Mallory Square, and end at Capt. Tony's Saloon with an alcoholic beverage. Read more
• You'll end at Capt Tony’s Saloon 428 Greene St, Key West, FL 33040, USA See address & details

• thomasdB217KU 0 contributions 5.0 of 5 bubbles Great Way to Learn about Hemingway and Key West This is a wonderful way to get to know Key West and appreciate the Key West that Hemingway knew. While the tour does not include a tour of Hemingway's residence on Whitehead Street, the tour does visit most of the places that Hemingway frequented. Our tour guide, Caleb, was excellent. A novelist himself, he had an excellent knowledge of Hemingway's life and writings. His stories about Hemingway and his influence on Key West added an extra dimension to our discovery of the history and culture of Key West. The tour included an early lunch at Kermit's Key West Lime Shoppe which included a slice of its famous Key Lime Pie. It was a great way to spend the morning. Read more Written 12 March 2024
• NorthStar781963 0 contributions 5.0 of 5 bubbles Great history review Caleb walked us around the neighborhood of Hemingway house and gave us a great history of the man and the area. He was very articulate and provided many insightful observations of lesser known facts about him. He also provided a good intro into the living history of Key West. The meal was very good too. Read more Written 10 February 2024
• gilliansT4056QY 0 contributions 5.0 of 5 bubbles Fun & Educational Caleb was excellent! We had a great time and learned a lot. This was our first time to Key West, and this tour gave us great insight into this remarkable town and its history. Read more Written 30 January 2024
• dsullybg1 0 contributions 5.0 of 5 bubbles Hemingway walking tour with additional island information. Lunch included Liz, the tour guide is friendly, informative and organized. It’s a well paced tour and we learned a lot about Hemingway and a bunch about the island also. Would recommend the tour to anyone who can handle an approximate 1.5 mile casual walk and can hear normally. It can be a little noisy along the way. Read more Written 5 January 2024
• Lana H 0 contributions 5.0 of 5 bubbles Excellent Guide Our guide was very knowledgeable and organized. She had lot of great facts about Key West and Hemingway. We would highly recommend this tour. Read more Written 17 July 2023
• stephaniepopik13 0 contributions 5.0 of 5 bubbles Key West Treasure Caleb was an awesome, knowledgeable tour guide. He answered all of our questions and generally made the experience worthwhile! Highly recommend this tour to anyone visiting Key West! Read more Written 6 June 2023
• toadsoup 0 contributions 2.0 of 5 bubbles So disappointed First of all, call this a Hemingway Walking Tour with lunch - not a food tour. The only time we ever got out of the sun and the too fast paced walk was a sit down lunch that we had to scarf down in 20 minutes. The guide did not interact with us very well, wanting to only walk and talk with one another person so we really couldn't hear that well (there were only 5 on the tour other than the guide). She also got some things wrong about Hemingway (getting confused on the wives and the number of years he was married). According to our guide, Hemingway must have been married at 10. Reason I know this is because we had visited the Hemingway House and had an amazing guide. Our tour guide here also didn't know Hemingway had a sister boat now located in the Bass Pro shop in Islamorada. So, if you want to know all about Hemingway, visit the house and take a guided tour and then go to Kermit's and get your own lunch, which BTW was very good, although we didn't know what we were getting (including a rum drink) until it was hastily plopped in front of us. We were so disappointed in this tour. But if you enjoy long, fast walks to a few signs that says Hemingway was here, and hopefully you are not a vegetarian or teetotaler, then by all means, you'll enjoy this tour. If not, well, then just pass on by. Of course, judging by all the favorable reviews of this tour, we may have just had a not-so-good tour guide. Read more Written 21 May 2023
• Kent E 0 contributions 5.0 of 5 bubbles Interesting, informative, and fun! We really enjoyed our tour and learning so many "behind the scenes" tidbits about Ernest Hemingway. The walk was comfortable and we were amazed how much we covered as we were constantly engaged by our guide, Caleb. He was interesting, funny, informative and really friendly. Great way to get some exercise and see some historic sites. We left the tour with ideas on new places to explore, which made this the ideal tour for us. Read more Written 10 May 2023
• Sherpa15373038123 0 contributions 5.0 of 5 bubbles Super fun walk! Great walking tour with a great tour guide!!!! So happy we did this! We learned not only more about Ernest Hemingway, but lots of very interesting information about Key West. Our guide also gave us new places to visit, that we didn’t even know about. Worth the money!! Loved it! Read more Written 17 March 2023
• boblN3071HP 0 contributions 5.0 of 5 bubbles Kudos! from Booking #153797151 for and Gregg and his "Hemingway Food & Walking Tour" Gregg, our guide, was fantastic, and made every part of the adventure "our favorite," and a definite "do-over." Thanks for connecting us with the best tour guide I've experienced in quite some time! Gregg provided unexpected charm and tons of high-quality, articulately-delivered, and well-researched information that only a true Freshwater Conch would be able to provide. I will definitely look forward to engaging Gregg again and recommend him highly for any gig he may be interested in! Everyone loved him. It shoukl be noted that the tour excludes the Hemmingway House. Many thanks again for a surprisingly enjoyable Key West experience! Read more Written 20 February 2023
• F2800FLnancyd 0 contributions 4.0 of 5 bubbles Good tour Nice tour. Stopped at some important points of interest. Included lunch with key lime pie and a drink at the end of the tour Read more Written 31 December 2022
• DayTrip492936 0 contributions 5.0 of 5 bubbles Great tour for both Hemingway history and Key West History Highly recommend this tour. Mark was very knowledgeable, friendly and made the history very interesting. We enjoyed that he wove Hemingway history in with the history of the island. Enjoyed the food provided. My husband liked the tour so much that he wanted to do the Buffet tour but unfortunately we didn’t have time left on our visit. Definitely worth checking out! Read more Written 29 December 2022
• Amy B 0 contributions 5.0 of 5 bubbles Great experience! Highly recommend!’ Our tour was great! The tour guide was awesome. It was educational and fun! We took many of his recommendations for food during our stay and they did not disappoint! He was very knowledgeable about key west and Ernest Hemingway! Highly recommend this tour! Best key lime pie I’ve ever had! Read more Written 13 December 2022
• dcnal 0 contributions 5.0 of 5 bubbles "The Tour also rises" - 5 stars! Our tour guide Caleb was an aspiring local author himself, so the stories he told of Hemingway were rich with lore and mystic. Caleb also added a few non-Hemingway Key West facts along the way. The tour was a well worth adventure, the food at Kermits KW pies was fresh and tasty with dessert being their famous key lime pie. Concluding the trip at the original Sloppy Joes/Captain Tony's with a Priate Punch was a perfect ending. Read more Written 26 November 2022
• J1258VCsandrab 0 contributions 5.0 of 5 bubbles Amazing, walking tour! Loved all the history of Hemingway! The lunch was delicious, and the rum drink was amazing! The tour through the house was not included, but we paid and went anyway. Seeing things that the tour guide told us about on the walking tour. We also bought two of Hemingway‘s books at the bookstore on the Hemingway property. Super fun and we knew nothing about this gentleman before the tour ha ha ha. Our tour guide Caleb was the coolest and funnest guy ever! His knowledge was the best! We would highly recommend this walking tour. Read more Written 24 November 2022

More to explore in Key West

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as waiting time, length of visit, general tips, and location information.

Buy it with

Jimmy Buffett Tour provided by Hemingway in Key West Tours

Cultural & Theme Tours

• Food, Wine & Nightlife
• Walking & Biking Tours

Are you interested in?

Popular Attractions

31 Attractions

Top Key West Tours

242 Tours & Activities

55 Tours & Activities

Jimmy Buffett Tour

• Text Message

Key West Tours

• All Key West Tours
• Craft Classes
• Catamaran Cruises
• Day Cruises
• Dinner Cruises
• Dolphin & Whale Watching
• Glass Bottom Boat Tours
• Night Cruises
• Sailing Trips
• Sunset Cruises
• Water Tours
• Cultural Tours
• Ghost & Vampire Tours
• Historical & Heritage Tours
• LGBTIQA+ Friendly Tours
• Literary, Art & Music Tours
• Private Day Trips
• Electric Car Rentals
• Deep Sea Fishing
• Flats Fishing
• Light Tackle Fishing
• Specialty Fishing Charters
• Cooking Classes
• Dining Experiences
• Street Food Tours
• Wine Tasting & Winery Tours
• Kid Friendly Tours & Activities
• Luxury Tours
• Romantic Tours
• Adrenaline & Extreme
• Fishing Charters & Tours
• Golf Tours & Tee Times
• Nature & Wildlife
• Custom Private Tours
• Private Sightseeing Tours
• Port Transfers
• Ports of Call Tours
• Adults-only Shows
• Theater, Shows & Musicals
• Attraction Tickets
• Museum Tickets & Passes
• Special Offers
• Water Parks
• Audio Guided Tours
• Bus & Minivan Tours
• Full-day Tours
• Fun and Games
• Golf Cart Rentals
• Half-day Tours
• Hop-on Hop-off Tours
• Night Tours
• Pedicab Tours
• Photography Tours
• Private Tours
• Self-guided Tours & Rentals
• Skip-the-Line Tours
• Sustainable Tours
• Trolley Tours
• Tuk Tuk Tours
• Vehicle Rentals
• Airport & Ground Transfers
• Airport Services
• Private Drivers
• Unique Experiences
• Bike & Mountain Bike Tours
• Walking Tours
• Boat Rentals
• Dolphin Tours
• Jet Boats & Speed Boats
• Jet Ski Tours
• Kayaking & Canoeing
• Other Water Sports
• Parasailing
• River Rafting & Tubing
• Scuba Diving
• Scuba Instruction
• Stand Up Paddleboarding
• Surfing & Windsurfing
• Water Equipment
• Waterskiing & Jetskiing
• Honeymoon Packages
• Wedding Packages

Attractions

• Things to do in Key West
• Marine Park
• Mallory Square
• Southernmost Point of the Continental USA
• Ernest Hemingway Home and Museum
• Mel Fisher Maritime Museum
• Harry S. Truman Little White House
• Duval Street
• Key West Lighthouse and Keeper's Quarters Museum
• Key West Historic District
• Best food & culinary tours in Key West
• Family-friendly things to do in Key West.
• Rainy day activities in Key West
• Senior-friendly tours, activities and things to do in Key West
• The Top 10 Key West Tours and Activities of 2024
• The best tours and activities for culture lovers in Key West
• Things to do in Key West this summer
• Top Day Trips from Key West
• Key West Event Calendar
• Good Friday in Key West
• Easter in Key West
• Memorial Day Weekend in Key West
• Cinco De Mayo in Key West
• Juneteenth in Key West
• 4th of July in Key West
• Labor Day in Key West
• Halloween in Key West
• Thanksgiving in Key West
• Veteran's Day in Key West
• New Year’s Day long weekend in Key West
• New Year’s Eve in Key West
• Hanukkah in Key West
• MLK Day in Key West
• President's Day in Key West
• Valentine's Day in Key West
• St. Patrick's Day in Key West

You will begin this 1 hour and 30 minute guided tour by meeting your tour guide, (who will be wearing a neon green shirt) at Margaritaville. Musician Jimmy Buffett arrived in Key West 50 years ago in 1971. This walking tour will take you to the locations around Old Key West that inspired his songs, where he played his first gig, some of his favorite watering holes, places he ate, bars he played in, and his recording studio. You will get to eat a slice of the best Key Lime Pie, before visiting the location of the first Margaritaville, Mallory Square, and end at Capt. Tony's Saloon with an alcoholic beverage.

Description

Stop At: Key West, Key West, Florida

Duration: 2 hours

• Reservations are REQUIRED for all bookings
• Book Your Package On-Line and Receive Your Confirmation
• Departure point: Detailed check-in instructions - including the address and parking information if applicable - will be included in your final confirmation email.
• Duration: 1 hour 30 minutes (Approx.)

Capt Tony’s Saloon, 428 Greene St, Key West, FL 33040, USA

What's Included

• A slice of Key Lime Pie and water
• Visit historical locations
• Alcoholic Beverages
• Gratuities (Optional)

What To Bring

• Confirmation Voucher (printed or mobile)
• Any required or suggested items listed on your confirmation email.

Additional Info

• Service animals allowed
• Public transportation options are available nearby
• Not recommended for travelers with poor cardiovascular health
• Travelers should have at least a moderate level of physical fitness

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

• For a full refund, you must cancel at least 24 hours before the experience’s start time.
• If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
• Any changes made less than 24 hours before the experience’s start time will not be accepted.
• Cut-off times are based on the experience’s local time.
• This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
• This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Average 4.85 out of 5 stars based on 46 traveler reviews collected by City Baloon Tours and partner sites such as Cool Destinations and TripAdvisor

Still have questions?

We’re here to help. Call Us , " data-help-center="text-us"> Text Us , or Live Chat to speak with a Destination Specialist Product code: C-302751P2

Similar Tours & Activities

Mel Fisher Maritime Museum Admission Ticket

Key West Photo Shoot at Your Resort or the Beach

Experience Key West Food Walking Tour

Travelers who bought this tour also bought.

Key West Original Island Jet Ski Tour

Key West Split Fishing Charter

Key West 4 Seater EZGO Golf Cart Rental

Free cancellation, log in or sign up, welcome to city baloon tours.

Log in to add things to your wishlist and access your bookings from any device.

Let's try that again

By selecting Agree and continue , I agree to Cool Destinations’s Terms of Service , Payments Terms of Service , and Nondiscrimination Policy and acknowledge the Privacy Policy .

Cool Destinations will send you members-only deals, inspiration, marketing emails, and push notifications. You can opt out of receiving these at any time in your account settings or directly from the marketing notification.

Sorting, ranking, and search results

City Baloon Tours wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through City Baloon Tours over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

Accessibility

Accessibility modes, online dictionary, readable experience, visually pleasing experience, easy orientation, accessibility statement.

• cityballoontours.com
• April 26, 2024

Compliance status

Screen-reader and keyboard navigation.

• Screen-reader optimization: we run a background process that learns the website’s components from top to bottom, to ensure ongoing compliance even when updating the website. In this process, we provide screen-readers with meaningful data using the ARIA set of attributes. For example, we provide accurate form labels; descriptions for actionable icons (social media icons, search icons, cart icons, etc.); validation guidance for form inputs; element roles such as buttons, menus, modal dialogues (popups), and others. Additionally, the background process scans all of the website’s images and provides an accurate and meaningful image-object-recognition-based description as an ALT (alternate text) tag for images that are not described. It will also extract texts that are embedded within the image, using an OCR (optical character recognition) technology. To turn on screen-reader adjustments at any time, users need only to press the Alt+1 keyboard combination. Screen-reader users also get automatic announcements to turn the Screen-reader mode on as soon as they enter the website.These adjustments are compatible with all popular screen readers, including JAWS and NVDA.
• Keyboard navigation optimization: The background process also adjusts the website’s HTML, and adds various behaviors using JavaScript code to make the website operable by the keyboard. This includes the ability to navigate the website using the Tab and Shift+Tab keys, operate dropdowns with the arrow keys, close them with Esc, trigger buttons and links using the Enter key, navigate between radio and checkbox elements using the arrow keys, and fill them in with the Spacebar or Enter key.Additionally, keyboard users will find quick-navigation and content-skip menus, available at any time by clicking Alt+1, or as the first elements of the site while navigating with the keyboard. The background process also handles triggered popups by moving the keyboard focus towards them as soon as they appear, and not allow the focus drift outside of it.Users can also use shortcuts such as “M” (menus), “H” (headings), “F” (forms), “B” (buttons), and “G” (graphics) to jump to specific elements.

Disability profiles supported in our website

• Epilepsy Safe Mode: this profile enables people with epilepsy to use the website safely by eliminating the risk of seizures that result from flashing or blinking animations and risky color combinations.
• Visually Impaired Mode: this mode adjusts the website for the convenience of users with visual impairments such as Degrading Eyesight, Tunnel Vision, Cataract, Glaucoma, and others.
• Cognitive Disability Mode: this mode provides different assistive options to help users with cognitive impairments such as Dyslexia, Autism, CVA, and others, to focus on the essential elements of the website more easily.
• ADHD Friendly Mode: this mode helps users with ADHD and Neurodevelopmental disorders to read, browse, and focus on the main website elements more easily while significantly reducing distractions.
• Blindness Mode: this mode configures the website to be compatible with screen-readers such as JAWS, NVDA, VoiceOver, and TalkBack. A screen-reader is software for blind users that is installed on a computer and smartphone, and websites must be compatible with it.
• Keyboard Navigation Profile (Motor-Impaired): this profile enables motor-impaired persons to operate the website using the keyboard Tab, Shift+Tab, and the Enter keys. Users can also use shortcuts such as “M” (menus), “H” (headings), “F” (forms), “B” (buttons), and “G” (graphics) to jump to specific elements.

Additional UI, design, and readability adjustments

• Font adjustments – users, can increase and decrease its size, change its family (type), adjust the spacing, alignment, line height, and more.
• Color adjustments – users can select various color contrast profiles such as light, dark, inverted, and monochrome. Additionally, users can swap color schemes of titles, texts, and backgrounds, with over 7 different coloring options.
• Animations – epileptic users can stop all running animations with the click of a button. Animations controlled by the interface include videos, GIFs, and CSS flashing transitions.
• Content highlighting – users can choose to emphasize important elements such as links and titles. They can also choose to highlight focused or hovered elements only.
• Audio muting – users with hearing devices may experience headaches or other issues due to automatic audio playing. This option lets users mute the entire website instantly.
• Cognitive disorders – we utilize a search engine that is linked to Wikipedia and Wiktionary, allowing people with cognitive disorders to decipher meanings of phrases, initials, slang, and others.
• Additional functions – we provide users the option to change cursor color and size, use a printing mode, enable a virtual keyboard, and many other functions.

Browser and assistive technology compatibility

Notes, comments, and feedback.

Welcome Fellow Foodies!

• Shop Foodies
• Foodies Essentials

Foodies South Shore, LLC

Local. Fresh. Lifestyle.

Travel · April 14, 2023

Florida Keys Itinerary: A Jimmy Buffett Inspired Road Trip

“The days drift by, they don’t have names, all of the streets here look the same…there’s so many quiet places, smiling eyes match the smiling faces…I have found me a home”

– Jimmy Buffett [lyrics from “ I have found me a home” in reference to his first couple months living on the island of Key West]

I have received numerous inquiries in the past few weeks about the Florida Keys and Key West; namely, because several friends and family members will be retreating to the United States’ southernmost island in February, March and April, and asked me for numerous recommendations, which ultimately warranted this blog post.

My obsession with Jimmy Buffett and Florida started when I was a kid, road-tripping to Florida and stopping in Jekyll Island, St. Augustine, Siesta Key, and eventually Englewood. However, I had never been to “Buffett Land,” also known as Key West. He was the first road-tripper from Nashville all the way to Key West, taking notes on his observations, and of course, which places had the best grouper sandwich and ice-cold beer. Countless hours of research, phone calls, and e-mails have resulted in the creation of a “Buffett-inspired itinerary,” so you can follow in the footsteps of his first adventure through the Florida Keys and eventually, Key West in the early 1970s.

You can find out more about the trip in Jimmy Buffett’s memoir, A Pirate Looks at Fifty , in which he describes the trip through the Keys as very “Kerouac-like” (author of the 1957 counter-cultural novel On The Road ) , and talking about what he felt at that time, which ended up being the trip that quite literally changed his life. Two other great books that contain information about the early years and Key West are A Good Life All the Way and Jimmy Buffett: The Key West Years . One final recommendation: buy the Essential Book of Boat Drinks – you’ll thank me later.

Pre-Trip Planning

• Book one-way ticket to Miami, FL from your home destination, with an early morning flight departure (6am)
• Contact one of the car rental companies (Hertz, Turo app, etc.) in the Miami airport and rent a convertible, or similar vehicle in which you can take the top down (we rented a black Mustang Convertible) so you can truly feel and enjoy the experience (Seven Mile Bridge, etc.)
• Book one-way ticket back to your home destination from Key West (for the day you plan to leave). Or, if you have the time, drive back up to Miami from Key West and stop at some of the places you may have missed
• If you happen to be staying one night in Miami – please, go to Mac’s Club Deuce . The place is something out of a movie (actually a lot of the neon memorabilia is leftover from the filming of Miami Vice). It was Anthony Bourdain’s favorite bar in Miami, and you should go so you can find out why. If anything, it is simply a quiet refuge away from the madness and the oppressive heat of the Miami strip. It is, I gathered, the oldest bar in Miami.

Florida Keys Itinerary

Once you leave Miami, it is about a 45-minute drive on US 1 until you reach a fork in the road – it is imperative at this point that you take Card Sound Road, which is the more scenic route and reminiscent of “old Florida,” and will also lead you to the first stop on the Itinerary, Alabama Jack’s.

Stop 1: Alabama Jack’s, Key Largo

Alabama Jack’s is an old crab shack reminiscent of “old Florida” that consists of plywood and a tin roof. But don’t be fooled – over 50 years old, this is a favorite dining and watering hole for locals, Buffett acolytes, and road-trippers alike. The bar overlooks a channel and sits between the mangroves, and often pelicans and alligators may pay you a visit. According to Buffett, get the grouper sandwich, some conch fritters, boiled shrimp, a few crab cakes, and in true Jimmy fashion: ice cold draft beer.

“There were several locals peeling shrimp at a wooden picnic table, tossing the hulls into the ocean…commercial crab boats lined the wharf…and a squadron of brown pelicans law in wait atop the dock pilings at the sight of shrimp hulls hitting the water” – Buffett on Alabama Jack’s, early 1970s

Stop 2: Caribbean Club, Key Largo

Second stop on the Buffett inspired road trip is the Caribbean Club in Key Largo. This is the actual site of the famous Humphrey Bogart and Lauren Baccall movie classic, Key Largo directed by John Huston. The back deck adorned with palm trees and a few docks, is still is basically untouched from the famous scene in which Bogie thwarts the gangsters plan to escape. The bar is a classic old Florida bar and vibe – old film memorabilia, pool tables, jukebox, interesting signs and wood carvings, and locals drinking Coronas accompanied by a pack of Marlboros and stories of the day’s fishing conquests. To this day, it remains one of my favorite beach-style bars because of the rarity and uniqueness as these bars do not really exist anymore.

“It was a bar like many others, but it wasn’t….faded stills from the classic movie lined the walls…I tried to place the real location with the action from the movie, and then walked out to the pier where Bogie thwarts the escape of the gangsters…I sat there and sipped my beer…knowing I would be associated with this world [Florida Keys and Key West] for the rest of my life…” – Buffett on the Caribbean Club, early 1970s

Stop 3: Robbies Marina Of Islamorada

Robbie’s Marina is a must-stop – voted one of the best stops in keys – grab a fresh grouper sandwich at the Hungry Tarpon Restaurant, a Rum Swizzle with Pilar Rum at the Thirsty Tarpon Bar, and check out the Tropical Open Air Market. Also, make sure you feed the tarpon, it is a great experience.

Optional Keys Bars (If You Don’t Want Your Adventure to End)

Lorelei Restaurant and Cabana Bar, Islamorada, Sunset Grille, Marathon, FL ; No Name Pub, Big Pine Key, FL

Key West Itinerary

I recommend you stay at the Casa Marina Resort (where we stayed) or the Southernmost Beach Hotel , or somewhere in that general area of the island. It was nice to party on famous Duval Street, and then have the option to retreat back to the quiet grounds of the resort and have a drink on the private, secluded beach. This area of the island is also convenient, because you are right next to the Southernmost Point Buoy which is an awesome place to take a picture as it is the literal Southernmost Point of the Continental Contigious United States – get there early, because it becomes insane with a tourist line by 9am. Lastly, you are also a two minute walk to one of the island’s best restaurants and bars (and my personal favorite), Louie’s Backyard .

First Order of Business (After Check-In)

Rent bikes! Make sure you rent bikes – I can not stress this enough. The island gets congested very quickly and early, and it is so easy to navigate and see so much more with your ten-speed. And yes, there are coozies attached to the bikes for those that want to do the “Duval Crawl.” Once you have a bike, the world is your oyster.

Bars, Pubs and Saloons

There are bars up and down Duval Street, but many of the famous ones are clustered towards the end of Duval, near Mallory Square. From the hotel, it is about a 15 minute walk; on bikes, 7 minutes.

*Favorite Bar/Restaurant Combo in Key Wes t* – Louie’s Backyard

Because of the ambiance, view, historical aspect, as well as excellent food and drinks. Louie’s Backyard, by far, is my favorite bar in Key West. It is the restaurant in which Buffett started playing in the early 1970s in exchange for beer instead of money; where he was married and divorced (not on the same night); and where he eventually landed an apartment next door and wrote the song “Tryna’ Reason with the Hurricane Season” about a hangover and not being able to “go at this pace very long” in which he stumbles over to Louie’s to get a much needed Bloody Mary.

Enjoy your time at Louie’s and savor the experience – also make sure you buy the Louie’s Backyard Cookbook, it is awesome!

*Second Favorite Bar* – The Chart Room

Because of vibe, uniqueness, and historical aspect, The Chart Room (Inside the Pier House Hotel) is my second favorite bar in Key West. After Louie’s you should immediately go here before it gets too crowded. This is a bar that has solidified itself against time, and was traversed by Jimmy Buffett, Hunter S, Thompson, Jim Harrison, Tom MCGuane, and may other famous literary giants, artists, and musicians. This is one of the old bars left of “Old Key West” and one of the former bartenders, Phil Clarke, was Buffett’s friend and inspiration for the famous song “A Pirate Looks at 40.”

*Third Favorite* – Schooner Wharf Bar

I love Schooner’s because it is an authentic Key West fisherman’s bar. Tall tales, awesome live music, happy and hour is from 7am to 11am. I inquired why so early, and the waitress responded: “how can you drink all day if you don’t start in the morning?” Also, while you are at Schooner’s make sure to visit Shrimpboat Sound , Jimmy Buffett’s recording studio!

*Fourth Favorite* Captain Tony’s (Authentic Key West Bar, original Sloppy Joe’s)

Captain Tony was the Mayor of Key West thanks to help from Buffett. The song “Last Mango in Paris” is about Captain Tony, and all he did for Jimmy in his early years in Key West. By the way, Captain Tony’s is the original Sloppy Joe’s Bar, where Ernest Hemingway would often frequent. Toss a quarter into the grouper’s mouth while you have your back to it after a couple drinks – allegedly it is good luck (or the bar just gives you a free drink. Either way, enjoy!

Other Favorite Bars (With Great Live Bands , Great Drinks, and Good Vibes)

Sloppy Joe’s (not the original), Irish Kevin’s , The Coconut Man in Mallory Square, Hogs Breath Saloon , Willie Ts , Original Margaritaville (get a margarita, they are incredible!), and Green Parrot Bar

Restaurants

*Personal Favorite* – Louie’s Backyard – incredible restaurant right on the ocean. Great spot for pre-gaming before heading out to Duval, or getting dinner on the way home after an early Duval trek. Also the restaurant deck is where Jimmy Buffett started out playing gigs in the 70s for free beer as his apartment was next door.

Blue Heaven

My favorite breakfast spot in Key West – cats run wild, chickens roam the grounds, and people start drinking champagne at 7am. Make sure to get the lobster benedict, and try the whipped Key Lime Pie!

Pepe’s Cafe , Banana Cafe , Le Crepere Cafe Key West , Cuban Coffee Queen

B.O.s Fish Wagon, DJs Clam Shack, Thirsty Mermaid, and Moondog Cafe

Get Dinner at Latitude’s on Sunset Key

Sunset Key is only a 5-minute ferry ride from Mallory Square in Key West. Latitudes, is the bar and restaurant on the island, and it makes for a wonderful evening for dinner. If you can, definitely go.

Louie’s Backyard – can’t stress it enough! The place is the real deal.

Other dinner spots : Santiago’s Bodega, Thirsty Mermaid, Blue Heaven, and any of the bars mentioned above

Kermit’s Key Lime Pie Shoppe

My favorite dessert of all time is Key Lime Pie, and the limes, are from Key West and the surrounding island. They are different than other limes. I think I tried the Key Lime Pie at eight restaurants. They were all incredible – Kermit’s is up there. Enjoy!

Papa’s Pilar Rum Distillery (Hemingway’s Family Distillery), Key West First Legal Rum Distillery , and Key West Trading Company

Hemingway Home and Museum

One of my favorite activities in Key West, was the tour of Hemingway’s House, which we did twice. He remains one of my favorite authors, and deserves so much respect for his contribution to the literary world in America. He lived in Key West from 1931-1939, and did some of his best writing in the studio that is connected by a bridge from his main home. He was so disciplined, that he would get up at 6am, no matter how hungover, and write until about 11am. He then would then trek to Duval Street and drink at the Original Sloppy Joe’s (now Captain Tony’s) and eventually stumble back to his home at night (using the Key West Lighthouse as his compass). And then do it all over the next morning. A true American legend and icon.

Shrimpboat Sound

This remains Buffett’s music studio, aptly named “Shrimpboat Sound,” which is still in use today and was used to make his most recent album, Life on the Flip Side. You will be able to recognize it by all of the stickers; it almost looks like a big white shipping container. When we were in Key West, we just missed Kenny Chesney leaving the studio; presumably recording a new country song with Buffett.

Other Activities

Get dinner on Sunset Key, catch a Mallory Square sunset, Butterfly Museum, bike to Fort Zachary Park and have lunch, Key West Conch Tour, Key West Lighthouse Tour, Harry S Truman White House Tour, ferry to and snorkel Dry Tortugas National Park, scuba diving around Key West, rent jet skis, rent a boat to the Snipes Keys or Ballast Key, go fishing for Tarpon, venture to Stock Island and check out Higfish Bar and Grille and have your fish you caught filet in front of you and cooked, check out the Key West Bookstore, picture at the “Mile 0” marker

Most importantly, the Keys and Key West are about going with the flow and doing what you feel is fun at the moment. Go down some side streets. Pop into a corner a bar not listed on this guide. Bike to an off-the-beaten-path beach. The island has a great vibe and you will love it. And, most importantly have a lot of fun and make some wonderful memories.

If you are not going to Key West this winter, here are a few books and early Buffett albums that are directly related to the Keys and Key West that can take you there.

Suggested Reading: A Pirate Looks at Fifty , Jimmy Buffett: The Key West Years ,

For True Parrotheads: A Good Life All the Way, Captain Tony: Life Lessons from a Legend

Early Albums on Key West: A White Sport Coat and a Pink Crustacean , Living and Dying in 3/4 Time , A1A , Havana Daydreamin’ , Changes in Latitudes, Changes in Attitudes , Son of a Son of a Sailor

*If you use this guide, please drink responsibly

You’ll Also Love

The Red Lion Tavern – Cozy Winter Date Night

Trending now, lobster boil on the spit join the newsletter to find out more.

The Foodies blog is a place to share our favorite places to eat, hidden gems, best places to drink, offer helpful recipes, go-to travel spots, DIY’s and how-to’s, and share the overall beauty of the South Shore and beyond.

Work With Us

• About Foodies
• Get in Touch

Shop My Favorites

foodiessouthshore

Copyright © 2024 Foodies South Shore, LLC

Book Direct and Save up to 25%

--> 25% Off --> --> 30% Off --> -->