hawaii sailing tours

• Paradise Sailing Hawaii

Kailua Kona Sailing Catamaran Charters - Big Island Boat Tours

Enjoy a true sailing experience with a small number of passengers during a Kona sailing charter on Hawaii's Big Island! Our beautiful new sailing catamaran features plenty of shade , comfortable cushioned seating with tables, nice clean toilet facilities and the roominess, stability and speed of the newest 36' sailing catamaran offering Big Island boat tours.  We offer a variety of Kona sailing charters including a relaxing Kona Sunset Cruise and private catamaran charters.

Because we are family owned and operated , we provide the kind of personal service only a small business can and the comfort of catamaran sailing without the big boat crowds . Please check out our reviews on GOOGLE and TripAdvisor to find out how much our guests enjoy sailing with us!

Our most popular Kona Sailing tours

4 hour private catamaran charter.

Have our beautiful catamaran all to yourself and spend the morning sailing, snorkeling & looking for wildlife. Snorkel equipment and refreshments are provided. BYOB STARTING AT $1,595 Click here for more details

Private Kona Sunset Cruise

Sail into the sunset aboard Kōlea on our  Sunset Sail and enjoy the beautiful  Big Island Sunset. Refreshments are provided.  BYOB STARTING AT $995 Click here for more details

CUSTOM PRIVATE CATAMARAN CHARTERS

Starting at just $995*.

Google Rating

5.0 159 reviews

Paradise Sailing Hawaii , Honokohau Marina Slip J24, 74-380 Kealakehe Pkwy, , Kailua Kona , HI 96740 , United States (US) - Phone: (808) 883-0399

Go on an Adventure

Best hawaii boat tours & cruises.

Click here for Port Waikiki cruises sailing daily from the Hilton Pier at Hilton Hawaiian Village Waikiki Beach Resort.

Hawaii Nautical is one of Hawaii’s largest family-operated ocean-activity providers, with a fleet of vessels islandwide serving many harbors across Oahu, Maui and the Big Island.

My wife and I did the sunset cocktail cruise today and it was awesome. One of best experiences here. We’ve done the submarine, the helicopter tour, waterfalls, etc but this has been easily the best adventure for the price. Completely worth it! The crew was amazing and the views were unreal! DO IT!

5 Star Google Review

Whale-Watching

Whale-watching tours offer the opportunity to witness these magnificent marine mammals in their natural habitat. Aboard a boat, participants can observe whales breaching, diving and swimming while learning about their behavior and conservation efforts.

Snorkel Tours

Join us for an unforgettable adventure as we cruise along the coastline, spot playful dolphins in their natural habitat and experience the wonders of swimming alongside graceful sea turtles with a snorkeling adventure. Our expert guides will lead you to the best spots to encounter these fascinating creatures, providing a memorable and educational experience for all ages.

Scenic Tours

Enjoy a sail, fresh breeze and beautiful sights of the Hawaiian Islands coastline on this scenic and invigorating tradewinds sail. Relax and enjoy a perspective you can only get at sea. See marine wildlife in its natural environment.

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Sunset Cruises

Experience the breathtaking beauty of a sunset on the water with our sunset cruises. Enjoy the stunning views while relaxing on board, siping a cocktail and taking in the tranquil atmosphere.

Luxury Charters

We offer an exclusive experience for those seeking a premium and personalized yacht charter. With a fleet of high-end vessels and a team of experienced professionals, we provide customized itineraries, gourmet cuisine, and top-notch amenities to ensure a seamless and unforgettable journey on the open sea.

Disney Catamaran

Experience the magic of Disney like never before aboard our luxurious catamaran. Relax and indulge in the enchanting atmosphere while enjoying first-class amenities and entertainment, perfect for a family vacation or romantic getaway.

Whales Guaranteed

Near Ko Olina, Waikiki, Kona and the Kohala coast, come enjoy sailing, snorkeling, dolphin- and whale-watching, sunset-and-fireworks dinner cruises and private charters, all with Hawaii Nautical! We are Hawaii’s first Dolphin SMART-recognized operator for proper viewing of dolphins.

  Waikiki, Kona and West Oahu servicing Aulani, a Disney Resort & Spa in Ko Olina (ask about Disney catamaran sailing excursions exclusive to Aulani guests); Four Seasons Resort Oahu, Marriott’s Ko Olina Beach Club; Beach Villas at Ko Olina; Hilton Hawaiian Village Pier; and convenient to Waikoloa, Four Seasons Resort Hualalai, Mauna Lani and the Kona-Kohala coast.

Whom We Work With

Working with the most premier brands to provide the most premier experience on the islands.

Dolphin SMART

Sponsored by the National Oceanic and Atmospheric Administration (NOAA), Dolphin SMART educates guests about dolphin conservation and advises not to seek activities that pursue close interactions with wild dolphins.

NOAA cautions against swimming with wild dolphins, as it may constitute harassment, which is illegal under federal law. Additionally, per NOAA,  “manta rays are inherently vulnerable ” and are on the Threatened Species list; swimming near them day or night disrupts their natural feeding patterns.

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Who We Are & The Hawaii Nautical Difference

Home | Whale-Watching | Dolphin Tours | Snorkel with Turtles | Sunset Cruises | Luxury Charters | Disney Catamaran

Business office: 808-234-7245 8 a.m. - 5 p.m. Hawaii Time

Questions?  Contact Us

Reservations office: 87-1988 Pakeke Street, Unit 4, Waianae, HI 96792

Corporate mailing office: 46-471 Hololio Street, Kaneohe, HI 96744

Waikiki Sailing Tours

Cruise aboard a private luxury yacht - waikiki, oahu, hawaii, sailing tours.

Private sailing and snorkeling tours in small, intimate groups for families and couples in Waikiki, Honolulu.  Book a tour with us and make memories that last forever.

Sunrise Turtle Snorkel & Sail

DURATION:  2.5 Hours |  7am and 3pm

• CAPACITY: Min 2 ppl |  Max 6ppl
• Semi Private Charter: $99/person
• Private Charter: $599
• USCG licensed Captain

Whale Watching Sailing Tour

DURATION:  2 Hours |  11am, 1pm and 3pm

• Semi Private Charter: $109/person

Diamond Head Sail & Swim

DURATION: 2.5 Hours | 8am, 11am, and 2pm

Friday Night Fireworks

DURATION: 2 Hours  |   6pm Friday Nights Only

Sunset Tour

DURATION: 2 hour s  |    5:00pm

• Private Charter: $599

Sunset Dinner w/ Private Chef

• CAPACITY: Private Dinner for 2
• Dinner w/ Private Chef: $1300
• 2 Days advance booking

Special Events

DURATION:  customized per chartered event

• Committal of ashes
• Private Parties
• Bachelor/Bachelorette
• Birthday parties
• Anniversary

Hawaii Sail Charters

Updates From This Business

We specialize in Private Boat Charters

Give us a call at (808) 936-4875 to book an… read more

Private Sailing, Snorkeling, and Whale Watching,

Join Hawaii Sail Charters on our Beautiful 40'… read more

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Highlights from the Business

Eco-friendly

Family-owned & operated

Kid friendly

Romantic vibe

Services Offered

Verified by Business

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Review Highlights

“ We had the best time with Captain Tim and we can not thank him enough for the amazing experience we had with our family. ” in 3 reviews

“ I've been on his sailboat once before and both times he provided a great and fun experience. ” in 3 reviews

“ We started out fishing and enjoying the view and then stopped for a snorkel at the most beautiful bay. ” in 3 reviews

Location & Hours

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74-380 Kealakehe Pkwy

Kailua-Kona, HI 96740

Serving Kailua-Kona Area

Amenities and More

About the business.

We invite you to join us sailing and snorkeling the tranquil, clear waters off the Kona coast of Hawaii on our beautiful 40-foot sailboat, the Moana. Our experienced captain and crew will strive to provide you with a unique and memorable experience. We only offer private charters, with a maximum of six guests. …

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Hawai'i sail charters is amazing!! Such a gorgeous boat, amazing crew, and Nick is the best captain ever!! Highly recommend booking with them for any of your sail adventures!!

We had the best time with Captain Tim and we can not thank him enough for the amazing experience we had with our family. His boat is beautiful and he was a great Captain. There is nothing like sailing in Hawaii.... And this is the boat to do it on.

See all photos from Jacquie J. for Hawaii Sail Charters

We found Captain Tim and his Moana sailboat simply by walking around the harbor and finding the PRETTIEST and CLEANEST boat. This sailboat was sparkling and stunning. Booking was super easy through his website and the journey was reasonably priced. Capt Tim reached out to get our food + beverage preferences and any allergies. I am actually gluten free and turns out that Capt Tim went out to THREE or more different grocery stores before the trip to find gluten free wraps / gf poke for me!! The amount of effort he put into finding gluten free was so sweet and generous. He also provided beverages (and adult beverages) for us - the boat was stocked up with anything we needed! Captain Tim and his crew went ABOVE and BEYOND to make our trip fun, safe, and memorable. The boat is prepped for anything we wanted to do - snorkel, fish, whale watch, just hang out! There is no generic set plan he had to follow for the day - it is really a personalized day based on what his guests want - Capt Tim is so accommodating. Only thing we wish we had done differently is go out earlier in our trip so we had time to book a second day!!! We will definitely be back for round two. THANK YOU CAPT TIM AND CREW! (GARY!)

See all photos from Chandler C. for Hawaii Sail Charters

Absolutely FANTASTIC!!!! By far the BEST experience we had in all of Hawaii. Let's start from the beginning....we're a family of four, husband and wife with two young men 14 and 19, on a bucket list vacation. Wife specifically asked for a sunset sail in Hawaii on a sailboat. Now, I'm no dummy, happy wife, happy life, I wasn't about to book a catamaran tour with 20 strangers, so I set off on my search. When I came across Hawaii Sail Charters and pictures of the beautiful Moana, I was sold, I had found what I had hoped would be exactly what she wanted. Booking the tour was simple, they asked for my wish list and length of time I wanted. We chose a sunset sail with fishing, snorkeling and paddleboarding if we could squeeze it all in. I got an email confirmation of our requests and a reminder email the day before our sail. In fact, the morning the day of our scheduled sail we got a call from them suggesting we move our scheduled time up a half hour as the sun was going down earlier and they didn't want us to pay for sailing in the dark, how consisiderate!!! That early evening we made our way down to the marina, and found the beautiful, impeccably clean, Moana sailboat, just short of 40 feet of absolute beauty!! We were greeted by Captain Nick and first mate Sam, short for Samantha I assume as she had quickly grabbed the attention of our two young men. We were welcomed aboard, given a quick tour, talked about our planned adventure, and were off. Honestly, we were blown away. A fully stocked cooler of beers, seltzer, juices and soft drinks, a bar with Mai Tais and Colladas. An endless supply of the most beautifully presented and delicious snacks one could ask for. From the most delicious white pineapple to the fresh macadamia humus, and fresh poke made 2 ways, to the hot delicious garlic shrimp, we were in heaven. And let's not forget about the activities, pulling out of the marina we saw a HUGE marlin caught as part of a tournament. Capt Nick maneuvered that 40 foot sailboat as close as he could so we could clearly see the winning fish, it was amazing. We headed out and saw baby spinner dolphins which we photographed and admired before we threw some lures in the water to see if we could catch some fish on our way to the snorkeling grounds. Once there Capt Nick and Sam went over the rules and gave pointers to all. Sam was the first one in the water, diving in to moor the boat, very impressive. They handed out top notch equipment and let us go off. The wife wanted to try paddleboarding and soon everyone was giving it a try, Heck even Capt Nick and Sam dove in, and actually found and showed us the biggest conch shell ever, it was so cool. We then admired the sunset and slowly worked our way back to port. Honestly we did a lot of cool things while we were in Hawaii, but the sail on the Moana was by far the greatest experience we had on our trip. The most beautiful boat, the nicest people, and the greatest service ever. If on the Big Island make sure you put this on your list. I promise you won't be disappointed!!!

This company is great! Can't say enough nice things. Tim and Mike took us on a lovely afternoon/sunset sail. It was awesome to have a private charter. Saw dolphins and beautiful sunset! Food, beverages and service were great. Tim is a highly skilled captain- very safe- and everyone had the Aloha spirit. It's clear Tim loves doing this work! Glad these guys were here to help us have an adventure. Thanks again.

My friend's brother booked this boat for a post COVID (well, intra-COVID) trip for his wife's birthday. There were five of us. The boat was spotless, the captain and his assistant were fabulous, and the music and food were really something - sushi and guacamole and fruit- really, it was 100% perfect from beginning to end! It was so relaxing and I, who is usually TERRIFIED of boats, forgot to be scared because they did such a great job. I'd do it again in a heartbeat.

Tim was an amazing host and guide. He made sure to ask what we wanted to do and customized the tour around that. All equipment needed for our day of snorkeling and sailing was provided for us. He has a beautiful boat that was clean and spacious, perfect for avoiding large groups. It was a nice change of pace to be able to sail instead of just cruising on another power boat. He provided delicious snacks and drinks for us as well. Definitely a highlight of our trip and will recommend him to anyone we know headed out to the big island.

Captain Tim is the best! I've been on his sailboat once before and both times he provided a great and fun experience. This last time we had a lot of dolphins around and we got to swim with them. There's snorkel gear on the boat so we didn't even need to bring our own. There were also snacks and drinks on the boat to quench our thirst along with reef safe sunblock in case we forgot to bring any. We did an incredible sunset tour. All thumbs up!

This sail boat was the highlight of our vacation!!! My family was so excited to have the whole boat to ourselves! We started out fishing and enjoying the view and then stopped for a snorkel at the most beautiful bay. We saw a turtle while swimming and as we left we saw a very rare Hawaiian monk seal! They offered the best fresh snacks including Poke, wraps and cold beverages! The boat had plenty of room to make ourselves at home! Thank you captain Tim for the beautiful day and experience! We will be back next time for another private sailing charter!

We booked this boat because it was one of the few sail boats that could take us snorkeling, fishing, had stand up paddle boards and we could stay out till sunset...pretty much everything you could want. It is beautiful 40 ft Beneteau, very clean and well equiped. The captain and owner, Tim was so great with everyone. He is a very experienced sailor and was quite comfortable letting us all steer the boat, and not just for 5 minutes, you really got to feel it as he gently coached you. Tim knew great snorkle spots that were not so crowded and the boat was easy to get on and off. The crew was very helpful and always there to help with everything. The food was really good and easy to eat onboard. I think he said guests can request special food too. I felt liked it was just the perfect day, so easy and relaxing, and just our friends which created a great atmosphere to catch up with each other and enjoy being out on the water. We saw a huge turtle as we left the Harbor which was a bonus. The dock was easy to find and parking was easy too. We will definitely be back for Whale season and Dolphins.Mahalo!

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• All Adventures
• Waikiki Sail & Snorkel Adventure

Diamond Head Sunset Cruise

Explore famous turtle canyons, private whale watching cruise.

• Friday Nite Fireworks Cruise

Offshore Fishing

• Private Sunset Dinner Cruise
• Interisland Overnight Adventures
• ASA Sailing School
• Event Planning
• Luxury 43 Ft Sailing Yacht
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Experience the Magic of Hawaii!

Sunset sails, snorkeling adventures, whale watching, friday night fireworks, explore turtle canyons, asa certified sailing school, anniversaries, bachelorette parties, memorials & ash ceremonies, catering photography, waikiki sail & snorkel adventure.

Oahu’s Best Snorkeling Tour features a three hour cruise aboard a private luxury yacht. Enjoy a leisurely sail off the idyllic coast of Oahu’s famous Waikiki Beach with stunning views and  a chance to see dolphins, sea turtles and whales in season.

Escape the crowds and let your captain guide you to a relaxing anchorage where you can snorkel with tropical fish, sea turtles and beautiful coral.  Invite your family and friends and make memories while your Captain and crew take care of the rest.

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Immerse yourself in a gorgeous Hawaiian sunset. Idyllic sailing awaits you with spectacular views of iconic Diamond Head and Waikiki. Catch a glimpse of dolphins, sea turtles, and whales in season.  Honolulu’s city lights provide an enchanting backdrop for your return to port.

Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with Sea Turtles and tropical fish. The crystal clear waters of Waikiki’s Famous Turtle Canyons reveal a kaleidoscope of colors and marine life. Discover the secrets of this diverse marine ecosystem as you swim among the colorful inhabitants and witness the beauty of Hawaii’s underwater world up close. Our Top Rated Sea Turtle Swim features a three hour private cruise aboard a luxury yacht. Get a chance to see dolphins and whales (in season) while taking in the magnificent views of Oahu’s Famous Waikiki coastline. 

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales.  Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for majestic whales. Dolphins, sea turtles, and manta rays are often seen while relaxing aboard with your family and friends.

Sport fishing from a sailboat is a true adventure!  We head offshore where the big fish are and sail fast to catch real gamefish like mahimahi, ono, and tuna. We do not fish the delicate reef ecosystem, those fish should only be caught on camera, and you can do that on our snorkeling tours. Offshore fishing in Hawaiian conditions can be physically challenging so be sure you are ready. We often see dolphins, sea turtles and manta rays while sailing offshore.

We offer beginner to advanced sailing and navigation instruction aboard private yachts in the Hawaiian Islands. Instructors are ASA Certified and dedicated to teaching you the skills required to be your own Captain. We give you the knowledge and experience to be confident and safe on all your sailing adventures- Whether you charter a boat from a local harbor, go on an exotic sailing vacation, or even buy your own boat.

Special Event Planning

Bring the Spirit of Aloha to your next Birthday, Anniversary, Hawaiian Wedding, or Corporate event. Let our preferred Honolulu event specialists assist you in making your event an unforgettable success! If you would like to have a Memorial at Sea or a Hawaii Ash Scattering we can help you create the right ceremony.

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Want your own private sunset tour? This is it! The tour was very professional as well as fun. Michelle made booking the tour very easy. Michelle and Will were very good on the open Ocean and very accommodating. Allowed music if you wanted and can bring whatever drinks you want. Will had just crossed the Pacific Ocean in a boat! Wow!

What to do with a dozen friends all in town at once? Our sunset sail was wonderful! Everyone had a lovely time, enjoying the beautiful skyline and horizon. The highlight of the trip was our close sighting of humpback whales! They were less than 30 yards away at times – it’s hard to say whether the kids or the adults were more excited! The crew was very helpful and the boat Tefiti (for sailing nerds) is beautiful, clean, in perfect condition, and amazingly set up for singlehanding – almost everything is automated to the point she almost sails herself. Not a spot of rust anywhere – she clearly gets a lot of TLC!

Our family of 10 rented the boat originally for two hours to take my husband’s ashes out to Diamond Head and scatter them in the ocean he loved so much and sailed so often. It was a Memory that the entire family will cherish forever. Michele and our captain couldn’t have been more accommodating. After we put his ashes into the water, we asked if it would be possible to stay out an extra hour so that we could all swim in the waters off Waikiki…and the two of them were totally good with that! Such a fun time after such an emotional day for us all. Michele was so good with the two youngsters we had with us…even providing brand-new life jackets for them…ages 6 + 7! It was sunset as we came into the channel…docking was a picture perfect ending to the afternoon. Thank you so much! We loved it and highly recommend this team for a perfect sail aboard the Beneteau 50 Te Fiti!

Had a great day with Honolulu Sailing Company. It was really nice to have a private yacht and avoid the crowds packed on other boats. Our family really appreciated that the captain and crew were fully vaccinated and it made the tour very relaxing. It’s hard these days to find something to do that feels safe. We booked a snorkel cruise and will book a sunset sail before we head home to Arizona.

When it comes to variety and quality in Hawaii water activities of all kinds, Hawaii Sail is the trusted expert.

Oahu Water Sports

“Dining Cruises, Sunset Snorkels, Pirates and Fireworks… Oh my.”

Maui Water Sports

“Molokini One of Top 10 Snorkel Spots in the World”

Big Island Water Sports

“Dinner Cruises, Whales, & Snorkeling”

Kauai Water Sports

“Explore the Incredible NaPali Coastline”

Dinner Cruises

Sail off into the sunset and enjoy a traditional Hawaiian buffet dinner. Perfect for a romantic getaway out on the water.

Snorkeling Tours

An entire world awaits just under the waves, full of tropical fish, colorful coral reef and even green sea turtles.

Shark Encounters

Enter the feeding grounds of the sacred Hawaiian shark with only a metal cage between you and the frenzy.

Parasailing Excursions

Float gently over the ocean while tethered to a boat. Enjoy the scenery from high above the island of Oahu.

Jet Ski Rentals

Speed on the water is best achieved on a powerful jet ski. You can also attempt to balance on the water-jet-powered Flyboard.

Land and Sea Tours

Why settle for one? Make a day of it and take advantage of the best tours offered on both the land and the sea.

We know Hawaii, We know the Pacific

We offer an array of sailing options to suit any interest..

Snorkel with the whole family, young and not-so-young alike! Keep you eyes peeled on a whale–watching excursion to see some of the world’s largest and most powerful creatures. Kick back with a frosty tropical cocktail on a relaxing dinner cruise while we sail around the calm waters of paradise. How about really getting the adrenaline pumping with a thrilling ride on a parasail, high above the beaches of Waikiki? Whatever the perfect marine adventure means to you, Hawaii Sail has got you covered. Let the experts show you what real Hawaii sailing is all about!

What our Guests Say About Us

Destinations in hawaii.

The very best spots, seen at just the right time, can reveal a whole world of enchanting plant and animal life in the waters surrounding the islands. That’s why our in-depth knowledge of the area is so vitally important. There are a lot of general Hawaii tours around, but our deep love of the ocean and its inhabitants makes all the difference. Once you feel it, you’ll know what we’re talking about. This intimate knowledge of the water and its surroundings also means that our staff are informed at all times about the weather and sea patterns. This makes them the most qualified to make sure that our visiting snorkelers and cruisers enjoy themselves in comfort and safety.

Parasailing in Hawaii

Above the sea.

Picture it: You’re strapped into a parachute harness and towed behind a motorboat. It’s similar to water skiing – until you gain enough speed to lift off the surface of the water and glide through the air behind the boat! The thrill of the takeoff is soon followed by awe and wonder as you discover breathtaking views all around you. We’ll take you soaring along the south shore of Oahu, where you can catch unforgettable views of Diamond Head, Waikiki, and the dramatic Honolulu cityscape.

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• (808)900-6070
• [email protected]
• Honolulu, HI 96813

Copyright 2023 Hawaii Sail

Hawaii Sailing Adventures, LLC

Private Charters in Maui, Oahu, Lanai, Kauai

Before or after your sailing trip

In addition to our own luxury catamaran and yacht charters , Hawaii Sailing Adventures recommends the following tours and excursions to further explore Maui, Kauai, Oahu and Hawaii.

Hawaii Forest & Trail Kailua-Kona, Hawaii

Maunakea Summit & Stars Adventure

Mauna Loa Helicopter Tours - Big Island Kailua-Kona, Hawaii

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Myths of Maui Luau at the Royal Lahaina Resort Lahaina, Maui

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Aloha Sunshine Tours Honolulu, Oahu

3A - Arizona Memorial Pearl Harbor & Historic Honolulu City Tour departing Waikiki Hotels

8A, 8B, 8C - Battleships of WWII at Pearl Harbor Tour departing Waikiki Oahu Hotels

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North Shore Adventure Tour

Pearl Harbor USS Arizona

And You Creations Honolulu, Oahu

Dolphins and You

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Aerial Challenge Course

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One-on-One Private Surf Lesson

SNORKEL AND SAIL

EXPERIENCE THE BRILLIANCE OF THE BIG ISLAND, HAWAII WITH A KONA BOAT TOUR.

HAWAIIAN OWNED & OPERATED

BOAT TOURS KONASTYLE®

KONASTYLE® OFFERS A VARIETY OF KONA BOAT TOURS EXPLORING THE COAST OF THE BIG ISLAND OF HAWAII. THIS IS YOUR CHANCE TO SNORKEL IN A MARINE SANCTUARY, SAIL INTO THE SUNSET, BOOK A PRIVATE CHARTER OR JOIN US ON A NIGHT MANTA RAY SNORKEL TOUR. OUR KONA SNORKEL TOURS ARE ALL ABOUT THE MAGIC OF THE HAWAIIAN SEA WITH SPECIAL EXPERIENCES FOR YOU ON THE HORIZON.

KONASTYLE® Private Charter

Any destination, anytime, book a tour.

• Boatbuilding
• Hanne's story
• Don's story
• Kevin's story

Hawaiian Canoe Sailing Tours

Sail a traditional Hawaiian canoe on Hilo Bay in the moonlight, experience the pristine beaches and rugged cliffs on the Kona coast, hike along the shore on a path in the lava where the Hawaiians have walked for centuries, explore steam vents and black sand beaches.

Wa'akaulua is the Hawaiian word for double hull canoe.  Captain Kiko is a sailor and experienced boat builder specializing in traditional Hawaiian canoes made by hand.  He has spent his entire life on the Big Island of Hawaii and can show you many off-the-beaten-path places on this island.  On his tours he will teach you about the history, geology and customs of this land and the sea surrounding it.  He will teach you to paddle a traditional Hawaiian canoe.  He might even teach you a few Hawaiian words and songs.

Come experience Hawaii with Captain Kiko.  It will be the highlight of your Hawaiian vacation.

All trips run from the mouth of the Wailoa River in Hilo, Hawaii.

Call captain kiko at (808) 895-3743..

copyright © 2019 by Kiko Johnston-Kitazawa

USE CODE "ALOHA" AND RECEIVE 10% OFF OF YOUR BOOKING!

Maui Sailing Canoe

Sail, snorkel, paddle - wailea, maui.

Native Hawaiian owned and operated since 2005

Outrigger Canoe and Turtle Town Snorkel Tours - Maui, HI

Native Hawaiian Owned and Operated since 2005 Book online now and get a discount!

Leave the crowds behind and sail into old Hawai’i

“eco-tour operator of the year 2009” — hawaii ecotoursim association.

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• Book now online and get a discount!

Sail Paddle Snorkel Tour

The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Juice/water and snorkel gear are provided. Explore the beautiful Wailea coast in a Hawaiian Outrigger Canoe!

• Hour Glass 2 hours
• User Ages 2+

PRIVATE CANOE EXPERIENCE

Great for group adventure! Bring up to 8 people with you and sail, snorkel, and paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe for 2 hours! We have 8:00 am and 10:00 am schedules available.

• Users Up to 8 guests

SAIL WITH US IN A HAWAIIAN CANOE!

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold drinks and snorkel gear are provided. Our adventure starts on Polo Beach in beautiful Wailea, Maui, where you will learn first hand about ancient Hawaiian sailing canoe tradition, construction, and navigation. We then launch the Hawaiian Sailing Canoe ‘Ke Anuenue’ straight from the beach just like the Hawaiians did in ancient times and sail on the gentle Wailea breeze for a unique perspective on the island of Maui.

Family owned and Operated since 2005!

This is an excellent way to experience a bit of old Hawaii. You learn more about the island as you skim along, just barely above the water. This is our favorite activity on Maui, and shouldn't be missed. Since this is a sailing activity, it is also ecologically friendly.

This was a very private low-key experience without the crowds of other tours. If you enjoy sailing and are interested in how the Hawaiians do it then this is the experience for you. Sage is very knowledgeable and easy to talk to and loves what he does.

We had a beautiful day on the water with Sage and his son. The boat is easy to get to from Kihei and we thoroughly enjoyed the snorkeling and sailing!

Great experience! We spent a peaceful and relaxing morning with Sage as our captain on his Hawaiian canoe. We sailed along the coast south of Waimea and learned about the history of Maui and the Hawaiian islands. Much more personal adventure than the big boat trips!

The 8 best Hawaii cruises in 2024 and 2025

C ruising the Hawaiian Islands offers U.S. travelers an immersive South Pacific escape with all the comforts of home. In fact, the Aloha State is in many ways an ideal cruise destination. It has year-round sunny weather, four main islands featuring varied topographies — including sandy beaches, cascading waterfalls, volcanic mountains and vibrant green valleys — and a wide array of land- and water-based activities.

The main caveat? Hawaii cruise options are somewhat limited — just a fraction of what's available in the Caribbean — and many itineraries involve multiday crossings from the West Coast. Only one cruise line offers Hawaii itineraries throughout the year; most others visit during specific months or when repositioning ships in spring and fall.

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Looking for the Hawaiian Islands sailing that's right for you? Here's a look at the eight best Hawaii cruises for every type of traveler.

Norwegian Cruise Line's 7-night Inter-island Hawaii

For travelers who want more aloha time than the typical eight-hour port call allows, Norwegian Cruise Line has a solution. Its 2,186-passenger Pride of America lets vacationers sample four Hawaiian islands over seven days, with overnights in Maui and Kauai, plus port calls on both Hilo and Kona on the island of Hawaii. In total, this itinerary offers nearly 100 hours of shore time.

Pride of America sails round-trip from Honolulu every Saturday year-round. As a U.S.-flagged ship, it's the only large vessel permitted to sail this way. Not only do you skip the long Pacific crossing that most cruise ships do to reach Hawaii, but passports are not required for U.S. citizens, and you can tack on pre- or post-cruise stays on Oahu.

The overnights on Maui and Kauai also mean it's possible to try several of Hawaii's signature experiences that most port calls don't allow. Passengers can catch dusk or dawn from atop Maui's massive 10,023-foot dormant volcano with sunrise and sunset excursions to the Haleakala Crater. And with the ship in port all night on Kauai, guests who want to enjoy traditional Hawaiian cuisine, music and hula performances can book the Luau Kalamaku for a fun evening out.

Pride of America, which has been cruising Hawaii since 2005, doesn't have the onboard thrills (race track, virtual-reality gaming, waterslides) of Norwegian's newer ships , but that's okay because the islands, not the ship, are your main destination. Its American-themed decor celebrates U.S. cities in a vibrant, and at times, kitschy way, but a 2021 refurbishment left its cabins and public spaces feeling refreshed.

Many of Norwegian's specialty dining venues (which incur a surcharge) are on board, including Cagney's Steakhouse, Le Bistro (here, it's Jefferson's Bistro), Moderno Churrascaria and Teppanyaki.

Who should go: Anyone seeking a convenient way to island-hop — and see a lot of Hawaii — by making the most of the generous shore time with a combination of independent exploration and shore excursions. Most sailings attract couples ages 50 and older, although summer and holiday sailings have plenty of families on board.

Related: Best time to cruise Hawaii

UnCruise Adventures' 7-night Hawaiian Seascapes

Cruisers seeking a less traditional, more carefree Hawaii experience can have it from November to April aboard UnCruise Adventures ' 36-passenger Safari Explorer. The seven-night Hawaiian Seascapes itinerary, which begins either on Molokai or the island of Hawaii, is an unconventional one designed for those who enjoy going off the beaten path in an intimate and more authentic setting. U.S. passports aren't required to sail.

UnCruise visits four islands — Maui and Lanai plus Molokai and Hawaii — and focuses on not only their striking landscapes and underwater beauty but also the cultural traditions, cuisine and music of the Hawaiian people. On Molokai, where there's not a single traffic light and the lifestyle is slow-paced, passengers get a chance to "talk story" with locals and enjoy a pa'ina (feast) and evening jam session. Lanai activities range from snorkel, paddleboard and kayak excursions to off-road adventures exploring the privately owned island's dramatic sea cliffs, red rock formations and vast fields once filled with Dole pineapples.

Most UnCruise sailings are during Maui's humpback whale season, so sightings while cruising off the coast of Maui are possible. You might also catch glimpses of dolphins and sea turtles. A "Captain's Choice" day is a wild card determined by the weather, marine life in the area and other factors, while the final two days are spent exploring the Big Island of Hawaii — including a hike up Hualalai volcano and a skiff ride along the rugged coast.

Constructed in 1998, Safari Explorer was designed with adventure itineraries in mind (in summer the U.S.-flagged ship repositions to Alaska). Its size allows it to navigate areas larger ships can't reach, which in Hawaii means bays and coves ideal for snorkeling or watersports.

With such a small number of passengers aboard, guests get to know each other — and Safari Explorer's friendly and knowledgeable crew — quite well. Passengers come together over meals featuring locally sourced ingredients, and as all UnCruise fares include unlimited wines, spirits and microbrews, shipmates can raise a glass without worrying who's buying a round. It all lends itself to an exclusive yet utterly relaxed week of cruising.

Who should go: The ship's laid-back onboard vibe paired with its land- and water-based activities make the Hawaiian Seascapes itinerary ideal for active travelers seeking a nature-focused itinerary — although cruise fares (which start around $5,900 per person) are among the priciest for a Hawaii cruise.

Related: Why it's easier to meet new people on a smaller cruise ship

Holland America's 17-night Circle Hawaii

Travelers who have more than two weeks to spare and who prefer to arrive in Hawaii via ship rather than an airplane can do so on Holland America 's 17-night Circle Hawaii itinerary. They'd better also love sea days because crossing the Pacific from San Diego or Vancouver to Honolulu and back requires 10 days.

That means passengers enjoy five or six days in Hawaii on Kauai, Oahu, Maui and the island of Hawaii. Some itineraries stay in select ports overnight. Cruises departing from San Diego also call on Ensenada, Mexico. With either departure port, passports will be required.

The itinerary is offered in 2024 and 2025 on the 2,650-passenger Koningsdam and 1,432-passenger Zaandam.

Travelers with more time on their hands can also visit Hawaii as part of longer Pacific island cruises with Holland America. Koningsdam will sail a 35-night Hawaii, Tahiti & Marquesas itinerary in 2025 that combines visits to four Hawaiian islands with calls on five islands in French Polynesia and Fanning Island, Kiribati (and 20 sea days).

Related: Holland America unveils epic cruise to Hawaii and Alaska for 2025

Zaandam will also sail 51- to 56-night Tales of the South Pacific itineraries that visit multiple islands in Hawaii and French Polynesia along with ports in the Cook Islands, American Samoa and Fiji.

Holland America is popular with cruisers ages 60 and older, many of them retired, who have time to enjoy longer itineraries on ships that offer good value with a focus on culinary and musical enjoyment. Two of Koningsdam's most popular venues are its live entertainment area with three venues — B.B. King's Blues Club (for Memphis-style rhythm and blues), Billboard Onboard (for chart-topping hits played by a live pianist) and Rolling Stone Rock Room (for a live band playing classic rock), and World Stage, a theater with a 270-degree screen used for both special BBC Earth in Concert and theatrical productions.

Onboard specialty dining options (at an added cost) include Pinnacle Grill for steaks and seafood, Tamarind for Pan-Asian cuisine and Rudi's Sel de Mer for French Brasserie specialties and seafood.

Who should go: Mature travelers who prefer not to fly and who enjoy a more traditional cruise experience. They should also love sea days as much (or even more so) than port exploration.

Related: 16 mistakes cruisers make on cruise ship sea days

Princess Cruises' 15- or 16-night Hawaiian Islands

Princess Cruises is also a good option for longer sailings. The cruise line offers numerous round-trip itineraries to Hawaii from Los Angeles, San Francisco and San Diego in the fall and winter.

The majority of sailings are aboard the 3,080-passenger Crown Princess and Ruby Princess from San Francisco, and the 2,600-passenger Grand Princess and 3,080-passenger Emerald Princess from Los Angeles.

Ships are in port for nine to 11 hours in Hawaii (Hilo), Kauai and Maui and for 16 hours in Oahu. Itineraries include a stop in Ensenada, Mexico (so passports are required), plus nine or 10 sea days.

The ships feature many of Princess' popular dining venues, including Alfredo's Pizzeria (a sit-down venue serving personal-size pizzas), Crown Grill for steaks and Sabatini's Italian Trattoria. There's plenty of outdoor space for soaking up the sun — including an adults-only sun deck — and a dazzling Piazza for enjoying cocktails, gelato and pop-up street performers.

Fans of Princess' Movies Under the Stars poolside screenings (with free popcorn) and Discovery at SEA enrichment programming will have ample time to enjoy these perks on a Hawaii sailing.

Who should go: These sailings will appeal to couples or groups of friends who prefer to have a wide choice of sailing dates, can take the time to enjoy a leisurely Pacific crossing and appreciate Princess' focus on quality cuisine and a sun deck designed for relaxation rather than thrills.

Related: Best Hawaii cruise shore excursions

Celebrity's 9- to 12-night Hawaii Cruise

Travelers seeking modern interior decor on a ship designed with couples in mind can visit Hawaii aboard Celebrity Cruises ' 2,852-passenger Celebrity Solstice or 2,918-passenger Celebrity Edge on itineraries ranging from nine to 13 nights — but only if the timing is right. That's because the line offers only two sailings per ship each year (in spring and fall) as the ships reposition between Alaska and destinations in the Pacific. The itineraries are one-way (Vancouver to Honolulu or vice versa) with passports required.

These cruises call on three ports on two islands: Honolulu (Oahu) and Hilo and Kona (Hawaii), with one or two overnights in port and 10 hours ashore on one-day visits. All include five days in a row at sea. Since the itineraries either begin or end in Honolulu, there's also a chance for some pre- or post-cruise exploration.

Sea days offer opportunities to enjoy the chic, grown-up ambience and amenities aboard these ships. Each vessel offers multiple complimentary and extra-fee specialty restaurants. Celebrity Solstice features Tuscan Grille for Italian specialties and steak and Murano for modern French cuisine, while Celebrity Edge offers the whimsical Le Petit Chef and the international Eden Restaurant.

Celebrity's signature Martini Bar and many other onboard watering holes keep the grown-up vibe going day and night. Choose cruise fares that include alcohol and Wi-Fi, or pay a lower rate and pay for your drinks as you go.

Who should go: The slightly shorter one-way sailings and the ships' contemporary ambience make these itineraries ideal for couples and groups of friends seeking a relaxing escape — especially Gen Xers in their 40s and 50s, who are Celebrity's target market.

Related: 6 national parks you can reach by cruise ship (and 2 are in Hawaii)

Carnival's 14- or 15-night Hawaii from Los Angeles

If fun is your cruise mantra, the "Fun Ship" brand Carnival Cruise Line offers a handful of round-trip sailings to Hawaii from Los Angeles (Long Beach) aboard the 2,984-passenger Carnival Radiance. Like other roundtrips from the West Coast, these itineraries spend just five days in Hawaii, offering eight to 14 hours of shore time in ports on four islands: Maui, Kauai, Oahu and Hawaii. Along with enjoying eight sea days, guests will also call on Ensenada, Mexico, so passports are required.

Carnival Radiance first sailed under that name in 2021, but it's not a new ship. Before an epic makeover, it sailed for the cruise line as Carnival Victory. Ship features include many of Carnival's signature complimentary and extra-fee dining venues, including Guy's Burger Joint and Pig & Anchor Bar-B-Que Smokehouse, BlueIguana Cantina, Fahrenheit 555 Steakhouse and Bonsai Sushi Express.

Additional guest favorite destinations on board include the RedFrog Pub, Alchemy Bar and WaterWorks aquapark. Expect high-voltage theater shows from Playlist Productions at night and poolside interactive contests by day.

Who should go: Socially inclined cruisers who love Carnival's emphasis on onboard fun and can appreciate a colorful ship with a lively ambience and lots of day and evening activities.

Related: Best Hawaii cruise tips for getting the most from your island-hopping trip

Royal Caribbean's 9- to 13-night Hawaii Cruises

A megaship cruise experience to Hawaii is available, too — with pricing that's quite affordable. Royal Caribbean cruises there on two vessels in one of its newer classes of ships: the 4,180-passenger Quantum of the Seas and Ovation of the Seas.

All are one-way cruises just before or after the Alaska cruise season (so late April or early October) between Oahu and Vancouver (or vice versa). The ships call on two Hawaiian islands and spend four or five days in a row at sea. Passports are required since these itineraries begin or end in Vancouver.

Ovation of the Seas and Quantum of the Seas feature a mix of thrills for all ages. These include RipCord by iFly simulated sky diving, FlowRider simulated surfing, bumper car racing in the SeaPlex indoor activity complex and the North Star sightseeing capsule, which ascends 300 feet above the top deck for 360-degree views.

Both ships also offer 14 dining venues, including the innovative Wonderland, Jamie's Italian by Jamie Oliver and kid-favorite Dog House, as well as bar options that include Schooner Bar for by-request piano tunes, Boleros for mojitos and merengue and Bionic Bar for drinks poured by robotic bartenders. Entertainment includes live cover bands in the Music Hall and multimedia music and dance performances in Two70.

Who should go: Cruisers who love a big ship with a wide array of dining choices, all kinds of evening entertainment and plenty of exciting activities to pass the time on sea days. Quantum-class ships are great for families, but the sail dates might not work for those with school-age kids.

Related: Do you need a passport for a cruise?

Viking's 16-night Hawaiian Islands Sojourn

For a guaranteed adults-only sailing in a relaxed, boutique-style setting, upscale cruise line Viking also offers round-trip Hawaii cruises from Los Angeles in late 2024 and early 2025 on its 930-passenger Viking Neptune.

What sets Viking apart from most of the other lines offering Hawaii cruises is that it includes a free shore excursion in every port. These include a highlights tour of Honolulu and Pearl Harbor on Oahu and a visit to a scenic waterfall and the Kilohana sugar plantation on Kauai. Additional excursions can be booked at an extra charge.

The 16-night Hawaiian Islands Sojourn sailings visit four islands — Hawaii (Hilo), Oahu, Kauai and Maui — and like other round-trip sailings from the West Coast include 10 sea days and a call on Ensenada, Mexico, so passports are required.

Viking Neptune will also do 32-night Grand Hawaii and Polynesia sailings round-trip from Los Angeles in late 2024 and early 2025 that visit four islands in Hawaii and four in French Polynesia.

The ship, which debuted in 2022, features sleek Scandinavian-inspired decor, a soothing spa with a complimentary thermal area, an aft infinity pool and hot tub, a panoramic Explorer's Lounge and five onboard restaurants. Specialty restaurant Manfredi's serves an extensive menu of Italian specialties, while The Chef's Table offers rotating five-course themed menus, including Asian, French and California-inspired.

In addition to the free shore excursions, pricing includes complimentary wine or beer with lunch and dinner, specialty dining at no extra charge, crew gratuities and transfers.

Who should go: Couples who prefer the quieter ambience of a ship that doesn't allow anyone under 18 onboard, doesn't have a casino and offers presentations by regional experts that enhance immersion into local culture. Viking cruisers are generally over age 55.

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Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.