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Hawaii Sunset Sails & Cruises

There are 93 tours in this category. Hawaii's Leader in Affordable Tours and Discount Activities

Sunset Sails & Cruises Sorted by Specific Tour

Hawaii Sunset Cocktail Cruise

Enjoy a Romantic Hawaii Sunset Cocktail Cruise!

Taking a Hawaii sunset cocktail cruise may prove to be among the most romantic and relaxing moments of your vacation. Sunset cruises probably won't rank high on your list of adventure items on your trip but may instead be the simple ending to a perfect day. Hawaii sunset cocktail cruises or sunset sails are differentiated from Hawaii Dinner Cruises in that they do not include a dinner. Usually these tours are a couple of hours in length and provide Hawaiian appetizers or 'pupu's' and some cocktails, wine and beer. Each sunset cruise boat is of course different and has a different food and drink offering but the one thing they will all have in common will be a great view of the sunset. The sunset hours are very special here and your sunset cruise in Hawaii will highlight this time of day as a central component of the tour's ambiance. Typically these moments of the day will be associated with calm ocean conditions as the ocean breezes will usually die down at sunset. In any event the locations your sunset cruise will depart from are generally chosen because of their particularly smooth ocean surroundings. These cruises are not the ones you would want to choose if you were interested in a vigorous ocean sail with plenty of wind to fill the sails but instead would be chosen because you wanted to enjoy the gentle breezes that are suitable for relaxation.

Hawaii Sunset Cocktail Cruises Are Found On Every Island!

Each island has its special spots that are suitable for a great sunset cruise. These locations are generally west-facing so as to capture the full impact of the setting sun and generally depart from the leeward coastlines of each island so as to provide the most protected and calm areas.

Oahu

On Oahu these departures are generally along the Honolulu and Waikiki coastline. 

Big Island

On the Big Island the area's best for departure would be along the Kona Coast from Kailua/Kona to Waikoloa.

Maui

Maui has two coastlines that are suitable for a great sunset cruise in Hawaii; the coastline from Lahaina to Kaanapali and from Maalaea Harbor

Kauai

Kauai's sunset cruises will depart from Poipu in the winter months and in the summer when the waves have calmed down the sunset cruises will generally depart out of Port Allen and take a longer four or even five hour cruise up to see the spectacular Na Pali Coastline.

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Sunset Sails & Cruises Sorted by Company

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(4 Reviews, 5 Stars)

Holokai Catamaran

1 Activity Option

Reserve a trip with the Holokai Catamaran

Go out on an adventure with Holokai Catamaran! Snorkeling, sailing, and great views of the island- we've got something the whole family will enjoy!
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(4 Reviews, 5 Stars)

Mauna Lani Sea Adventures

1 Activity Option

21' Power Catamaran, 50' Sailing Catamaran

The beautiful Mauna Loa Resort in Waikoloa is the departure point for all the activities provided by the Mauna Lani Sea Adventures. Pristine snorkel adventures, scuba diving trips, sunset sails and whale watching trips in season are all available. The 55' Polynesian style catamaran 'Winona' carries intimate groups of passengers on tours along this gorgeous coastline.
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(4 Reviews, 5 Stars)

Port Waikiki Cruises

2 Activity Options

54' Catamaran

If sailing is truly your ultimate objective in going out on a boat you will be thrilled with a ride on the sailing boat Paragon. The Paragon is a 47' sailing catamaran that is designed for these waters and designed for speed. There are not that many boats that pass through these waters that could go faster than this one.
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(3 Reviews, 5 Stars)

Atlantis Adventures

6 Activity Options

Submarine tours of Hawaii.

Atlantis Adventures will provide you with an opportunity to dive in absolute comfort in a 'state of the art', window filled submarine to a depth of about 100' for about forty minutes. Very spacious and air-conditioned these vessels hold just under fifty passengers as they are taken on one of the most unique rides of their lifetime.
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(3 Reviews, 5 Stars)

Hang Loose Boat Tours

1 Activity Option

Hang Loose Boat Tours

Wild dolphin watch & snorkel, evening sunset & manta snorkel, Kealakekua Bay snorkel.
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(3 Reviews, 5 Stars)

Maui Ocean Charters

1 Activity Option

Maui Ocean Charters

Set sail with Maui Ocean Charters on their sailboat "Shadowfax". Trips are available that last anywhere from a few hours to a few days or more!
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(3 Reviews, 5 Stars)

Hawaii Nautical

5 Activity Options

Leid Back' Dinner Cruise, Snorkeling and Dolphins, Whale Watch off the leeward coastline,Oahu Scuba

Hawaii Nautical offers a large variety of boat tours throughout the island of Oahu and on the Big Island of Hawaii. Snorkel tours and dolphin watches are offered in the mornings and the afternoons and in addition they offer sunset sails, dinner cruises, scuba and snuba options, whale watching in season and private charters.
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(3 Reviews, 5 Stars)

Trilogy Excursions

3 Activity Options

64' - 55' - 51' Sailing Catamarans, 55' Sailing Catamaran, 55' Catamaran to

One of the most popular and respected boating companies on Maui is Trilogy which has been in operation here since 1973. Though being a large company now, operating seven 50' range sailing catamarans, they are still the family owned operation that was begun by Eldon Coon and his two sons, Jim and Randy. Today they offer sailing tours to Lana'i, Molokini, the West Coast of Maui and an assortment of shorter sunset and sailing options and whale watches.
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(2 Reviews, 5 Stars)

Anelakai Adventures - Big Island

2 Activity Options

Kayak with Anelakai Adventures

Anelakai offers kayak, outrigger canoe and stand up paddling adventures off the Kona coast on the Big Island of Hawaii.
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(1 Review, 5 Stars)

Alii Nui Sailing Charters

2 Activity Options

Dinner cruise with hotel pickup.

The one of a kind, luxury catamaran Alii Nui departs from Maui's Maalaea Harbor and offers a variety of sail options which include Molokini snorkel tours, sunset sails, dinner sails and whale watches. All the specialty details have been included on all its tours to provide a privileged ocean experience. Snorkel tours include hot showers on board and large terry beach towels for your personal use. Dinner cruises are limited to 32 guests and even complementary pick-up is included on its whale watches.
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(15 Reviews, 4.9 Stars)

Scotch Mist Sailing Charters

2 Activity Options

50' Sailing Yacht, 50' Santa Cruz Sailing Yacht

The Scotch Mist is a 50' Santa Cruz Sailing Yacht which carries 18 passengers and offers sailing and snorkel charters off the coast of Maui. Having been the winner of the coveted Victoria to Maui Yacht Race in 1984, this vessel is a perfect choice to enjoy the waters off the coast of Maui and Lanai. She offers sailing and snorkel tours, sunset sails, trade wind sails and whale watching in season.
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(29 Reviews, 4.9 Stars)

Maita'i Catamaran

2 Activity Options

Waikiki Sailing Charters and Booze Cruises

The 44' sailing catamaran, Mai Tai, has been one of the most popular boats we have ever had on Waikiki Beach. Leaving right from the sand between the Sheraton and the Halekulani this 47 passenger boat will take you out for a day sail, a snorkel or a sunset sail and a view of the Waikiki Coastline and Diamond Head.
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(9 Reviews, 4.9 Stars)

Kauai Sea Tours

5 Activity Options

24' Rigid Hull Inflatable Rafts, Lucky Lady' 60' Sailing, Power Catamaran

Kauai Sea Tours is a large charter boat company that offers tours off the coast of Kauai and particularly the NaPali Coast with its beautiful 'signature' boat , Lucky Lady. In addition it also provides romantic dinner cruises and whale watches and also has a fleet of specially designed raft boats which are great for exploring caves, snorkeling and racing dolphins.
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(8 Reviews, 4.9 Stars)

Blue Dolphin Charters

3 Activity Options

56 foot wide-beam sailing Trimaran, 27' Raft and 63' Catamaran

Blue Dolphin Charters offers spectacular motor sailing cruises to the NaPali Coast of Kauai and to the 'forbidden island' of Niihau. In addition Blue Dolphin also offers whale watches, snorkeling, snuba, dinner cruises, sunset sails and rafting excursions. All emphasis is placed upon customer comfort and its large boats each maintain large walk-in restrooms, fresh water showers and plenty of deck space.
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(7 Reviews, 4.9 Stars)

Pride Charters

1 Activity Option

65' Maxi Catamaran, 65' Catamaran

The Pride of Maui is one of the largest and most stable power catamarans available in Maui's fleet of boats. Leaving from Maalaea Harbor the 'Pride' offers tours to Molokini in the mornings but will also operate beautiful sunset cruises a few times a week and in addition will provide one of the most comfortable boats for whale watching in the winter months.
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(13 Reviews, 4.8 Stars)

Holo-Holo Charters

3 Activity Options

61' and 48' Sailing Catamarans, 38' Raft

Holo Holo Charters offers a variety of boat tours on Kauai on large, powerful and stable catamarans. Tours include beautiful snorkel and dolphin watch excursions to the NaPali Coastline, raft tours of NaPali during the summer months, dinner sunset cruises, whale watching and tours to the forbidden island of Niihau.
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(6 Reviews, 4.8 Stars)

Sea Maui

1 Activity Option

Snorkeling, Whale Watching, Sunset Sails & Private Charters

Sea Maui II is a beautiful 55 foot power sailing catamaran, and the new Sea Maui III is a 65ft luxury sailing catamaran, they both depart from Kaanapali Beach. They offer a variety of snorkeling trips, whale watching, and sunset sailing options daily. Sea Maui has consistently been awarded "Maui's Best Boat Tour" for 2017, 2018, 2019 & 2020! Food is provided by the award winning Chef Joey Macadangdang of Joey's Kitchen.
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(34 Reviews, 4.8 Stars)

Teralani

2 Activity Options

65' Catamaran, 64' Sailing Catamaran, 65' Sailing Catamaran

The 65' sailing catamarans of Teralani Charters offer snorkel sails along the West Coast of Maui as far up as Honolua Bay, offer dinner cruises leaving off the white sands of Kaanapali Beach and offer spectacular whale watches during the winter months. Sailing will generally be a part of all cruises, weather permitting, and the stiff afternoon winds off the western shores usually provide some adventure and excitement. Evenings cruises however usually just have a gentle breeze.
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(33 Reviews, 4.8 Stars)

Captain Andy's Expedition

3 Activity Options

55' Sailing Catamaran, 55' Gold Coast Yachts, 30' and 38' RAIV

Captain Andy's Sailing Adventures for years has offered tours to see the spectacular NaPali Coastline of Kauai. Sailing large and luxurious Gold Coast Yacht Sailing Catamarans, Captain Andy's will take you snorkeling and dolphin watching as well as provide romantic dinner and sunset cruises. In addition you can enjoy rafting adventures to the NaPali Coast.
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(7 Reviews, 4.7 Stars)

North Shore Catamaran Charters

2 Activity Options

40' Sailing Catamaran, 40' Catamaran

The beautiful North Shore of Oahu provides the seascape for one of the most majestic boats on the island, the Ho'o Nanea, operated by North Shore Catamaran Charters. This 19 passenger, 40' sailing catamaran is one of the fastest on the island and offers fabulous sunset cruises, picnic snorkel sails and whale watching in season.
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(22 Reviews, 4.7 Stars)

Body Glove

1 Activity Option

65' Custom Catamaran, 51' Trimaran

Kailua Kona's Body Glove Charters offers snorkel and dolphin watching tours on a daily morning charter, dinner cruises in the evenings, a historical luncheon cruise, SNUBA diving and a whale watch during the winter season. If you are interested in a wonderful 3 hour coastal tour without the snorkeling, Body Glove is the only game in town.
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(8 Reviews, 4.6 Stars)

Paragon Sailing Charters

2 Activity Options

47' Sailing Catamaran

Certainly one of the very fastest boats found in the islands is the 47' customized sailing catamaran, Paragon. Paragon Sailing Charters offers a number of choices for boat tours ranging from morning sails to Molokini; Day Trips to Lanai; Sunset Sails; and Performance Sails.
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(23 Reviews, 4.6 Stars)

Star of Honolulu

8 Activity Options

Lunch and Whale Watch, Sunset Sails, Sunset Dinner Cruise

The 232' Star of Honolulu is the largest dinner cruise boat in Hawaii, has four levels and seats as many as 1500 people. Choose a dinner and show package from the 4 tiers of dinner options; Luxury 7-course, Deluxe 5-course, Casual 3-course or the Buffet dinner, all at varying prices. A smaller vessel, Starlite, seats only 149 passengers and provides dinner cruises as well. Each dinner option is served on its respective deck. In the winter months the Star of Honolulu also provides whale watches.
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(4 Reviews, 4.5 Stars)

Gemini Charters

1 Activity Option

64' Sailing Catamaran

Gemini Charters offers sailing tours that depart off of Kaanapali Beach and has done so for over 30 years. They offer multiple tours which include a sail and snorkel up the coast to Honolua Bay when weather permits, a delightful champagne sunset sail and whale watching tours in season. Their seaworthy 64' Sea Runner Sailing Catamaran is an excellent choice for a real sail.
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(39 Reviews, 4.5 Stars)

Hawaii Ocean Project

1 Activity Option

118' Motor Yacht.

The environmentally conscious Hawaii Ocean Project operates a number of tours out of the West Side of Maui port of Lahaina Harbor. Their touring options include day tours and ferry trips between Maui and Molokai, dinner cruises, sunset cruises, snorkeling tours to Lanai and whale watches. Marine naturalists will be on board to explain the marine life and ecological education is the underlying foundation of all its activities.
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(10 Reviews, 4.3 Stars)

Makani Catamaran

2 Activity Options

65' Sailing Catamaran

One of the most beautiful sailboats sailing the waters off the coast of Waikiki is the Makani Catamaran. This 64' x 32' Cat is one of the very fastest on Oahu often achieving speeds of over thirty knots. Flush with the most modern amenities you will be able to enjoy a wonderful sunset sail, a coastal daytime sail and a snorkeling excursion.
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(11 Reviews, 4 Stars)

Pacific Whale Foundation

9 Activity Options

52' and 60' Power Catamaran, 52' and 65' Power Catamaran, 65' Power Catamaran, 65' Catamaran

The Pacific Whale Foundation is one of the main companies we have on island that goes out in search of the whales during the winter months. In addition, throughout the year they also offer boat tours to snorkel at Molokini, dolphin watches that look for dolphins and snorkel off the coast of Lanai and have rigid hull inflatable tours that visit the back side of Lanai.
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(10 Reviews, 4 Stars)

Kamanu Charters Inc.

1 Activity Option

36' Sailing Catamaran

You'll enjoy "real sailing", snorkeling and whale watching on this trip with Kamanu Charters on their 36' custom designed sailing catamaran "Kamanu" to Pawai Bay. This area, located just north of Kona, is under State Fishery Management . The bay is within the Queen Liliuokalani Trust Land at Kaiwi Point and it is private. They also offer night manta ray snorkels.
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Makena Boat Charters

1 Activity Option

Makena Boat Charters

If you're staying on the south shore of Maui in the Kihei area, Wailea or Makena a really good choice for a snorkeling tour would be on the 65' sailing catamaran "Kai Kanani". This boat was built in 2007 and is a state of the art custom motorized sailboat. The location of the departure point for this boat is one of the very best because it is located just off the coast of Molokini, perhaps a short fifteen minute ride away.
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Hawaii Glass Bottom Boat

2 Activity Options

Hawaii Glass Bottom Boat

The Haleiwa Queen is a new 49 passenger glass-bottom viewing boat offering day and sunset cruises as well as the ever popular Friday Night Fireworks Cruise for a wonderful display in the sky and in the sea.
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Ocean Joy Cruises

2 Activity Options

Kai Oli'Oli a 61' power catamaran

One of the most scenic coastlines on Oahu is the West Coast above Waianae near Ka'ena Point. Ocean Joy Cruises specializes in touring this area which is great for snorkeling but is extremely famous for its dolphin sightings. Their large and stable 61' power touring catamaran has all the comfortable features to make this outing a great day on the water.
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Paradise Helicopters

2 Activity Options

Scenic Helicopter Tours of Oahu, Pearl Harbor Flights, Door's Off Adventure Tours

Paradise Helicopters is one of the premier helicopter touring companies that services both the Big Island and Oahu. One of the biggest differences between this company and many others is the fact that they will offer you the opportunity to take a flight with the doors off. As nerve racking as that may sound, you are completely strapped in an just a secure as you would be in an enclosed helicopter. The big difference is that your view from this perspective will be absolutely amazing.
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Tradewind Charters, Inc.

2 Activity Options

Oahu Private Sail & Snorkel, Mimosa Sunrise, Sunset Dinner, Whale Watch Tours, Ash Scatterings

Tradewind Charters specializes in private charter tours. The maximum of only twelve passengers on the 43 foot sailing yacht or 40 foot sailing catamaran creating an intimate non crowded atmosphere. Our 50 foot motor catamaran for larger groups up to 49 guests. With additional options for catering or an on-board bar guests can really create their own adventure at sea. If you're on Oahu for a vacation or event check out Tradewind Charters.
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Kona Snorkel - Noa Noa

1 Activity Option

Kona Snorkel  - Noa Noa

Kona Snorkel offers morning and afternoon snorkeling and sailing on the "Noa Noa," our 50 foot sailing catamaran. Certified for 43 passengers and permitted for operations from Kailua pier, she boasts roomy seating in an open-air shaded cabin and up front in netted trampolines on each side of our retractable swim ladder. She provides a comfortable ride, safe and easy water access and is equipped with a fresh water shower and his/her restrooms.
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Makai Adventures

2 Activity Options

Makai Adventures

Come experience all that West Maui has to offer with Makai Adventures on Kainalu, our 37' powerboat. Whether you want to go fishing, snorkeling or just cruise the coast, Kainalu will be able to get you there FAST!
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Kaha Loa

1 Activity Option

Make a reservation for the Kaha Loa

Kaha Loa is a 26-foot Glacier Bay power catamaran, perfect for cruising the waters around Lahaina and Maui. This boat features a shaded canopy top, an onboard marine head, fresh water shower, a full-feature stereo (feel free to bring your own music and we play it for you) a swim platform with ladder. There is plenty of seating on this boat, capable of carrying up to 10 guests, we only take a maximum of 6 guests in the interest of your comfort. The forward bow seating area is a very popular feature and this boat will reach speeds up to 28 knots, depending on ocean conditions.
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Sea Monkey

1 Activity Option

Sea Monkey -  a 32' sport yacht offering private tours

Sea Monkey is a perfect boat for a private charter of up to 6 for your family or special small group. Spend a day or watch the sunset on the water.
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Aloha Dolphin Tours

1 Activity Option

Aloha Dolphin Tours - 25 Foot Power Catamaran, Group and Private Cruises

Aloha Dolphin Tours offers a variety of sea tour choices for exciting ocean adventures. Ideal for small group or intimate private charters this power catamaran makes Kealakekua Bay accessible to enjoy with your family and friends.
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Hawaiian Boating Adventures

1 Activity Option

Grady White, 30', Power Cat, catamaran design, twin 200 hp Yamaha engines

Design your own customized ocean adventures on the Big Island of Hawaii and choose both how long you want to go out and what ocean activities you want to do on your special tour.
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Hawaii Pirate Ship Adventures

2 Activity Options

Hawaii Pirate Ship Adventures - Sailing tours on the 85' Spanish Galleon

Featuring unique day and night sailing tours with the pirate theme on an 85 foot pirates galleon. Tours go out for approximately an hour and a half along the Oahu coast with opportunity to dress up and participate in on-board activities.
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And You Creations

1 Activity Option

And You Creations - 55-foot Luxury Tour Power Boat, Group and Private

And You Creations offers a an exclusive Dolphin Swim and Snorkel Tour, a Circle Island Sites and Food Tour and a Manoa Falls Hiking Adventure, all with Waikiki Hotel pick up. They offer Japanese translation on these exciting ocean and land adventures. Ideal for your family and friends!
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Mana Kai Catamaran

2 Activity Options

Waikiki Sailing Catamaran Charters

Come aboard the Mana Kai for an unforgettable sail that shows you the island of Oahu from a unique perspective. Standing 32 feet long and 16 feet wide, the Mana Kai Catamaran accommodates up to 26 passengers. Based in Waikiki Beach, our famous Hawaiian Rainbow sail, lounge net, restroom, and a pleasant sound system add to your sailing pleasure.
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North Shore Sailing Adventures

1 Activity Option

40' Sailing Trimaran Boat

North Shore Sailing Adventures sails out of Haleiwa Harbor to explore the beauty of the North Shore in a fast or leisure sail that is comfortable, and in a safe atmosphere. Areas we sail to: majestic Waimea Bay, the 7 Mile Miracle of the North Shore, Ka’ena Point and outside the Harbor depending upon the season.


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Kainani Sails

2 Activity Options

Maui Sailing Charters

Private sailing charters aboard a 45' Beneteau Oceanis, Maui's newest monohull charter yacht. Come on board for an exclusive, personalized and memorable experience for up to 6 people. Sailing, snorkeling, wildlife, sunset cruises, sightseeing, celebrations, proposals, memorials and even elopements... anything is possible!
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