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Hawaii Sunset Sails & Cruises

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There are tours in this Category that range in price from $24.95 to $3500.00

Sunset Sails & Cruises

Enjoy a Romantic Hawaii Sunset Cruise!


Taking a Hawaii sunset cruise may prove to be 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 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 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.


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


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


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'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.

Look for this symbol in the tour descriptions below to indicate if it is Pride of America compatible.

Sunset Sails & Cruises Sorted by Specific Tour


Sunset Sails & Cruises Sorted by Company

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(4 Reviews, 5 Stars)

Hula Girl

3 Activity Options

65' Sailing Catamaran

You would be 'hard pressed' to find a more beautiful sailboat on Maui to take out on a snorkel sail, whale watch, dinner or sunset sail or a private charter. This multimillion dollar state of the art 65'x35', 90' wing mast sailing catamaran is designed for sailing and for maximum comfort. In addition it comes with its own full galley and private chef so all your meals will be prepared custom just for you.
More Info / Buy Now


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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)

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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(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

4 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)

Trilogy Excursions

2 Activity Options

64' - 55' - 51' Sailing Catamarans, 55' Sailing Catamaran, 55' Catamaran to Molokini, 55' Sail Catam

One of the most popular and respected boating companies on Maui is the Trilogy which has been in operation here since 1973. Though being a large company now, operating six or so 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 Lanai, Molokini, the West Coast of Maui and an assortment of shorter sunset and sailing options and whale watches.
More Info / Buy Now


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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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(2 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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(1 Review, 5 Stars)

Hawaii Nautical

4 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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(1 Review, 5 Stars)

Kainani Maui Sailing Charters

2 Activity Options

Kainani Maui Sailing Charters

Her modern yacht shape, spacious interior, and blue water sailing capabilities make her the perfect Hawaii sailing charter boat. She is also available for Memorials at Sea or Ash Scattering Services and special requests.
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(1 Review, 5 Stars)

Hawaiian Outrigger Experience

1 Activity Option

Book the Hawaiian Outrigger Experience.

Experience and relive a part of Hawaiian History as your cultural guides teach you traditional chants (oli), ancient myths, legends and historical facts. In honoring the wisdom and knowledge passed on by generations from ancestors. Offered daily Hawaiian Outrigger Canoe Tours depart from Wailea Beach in South Maui.
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(12 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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(18 Reviews, 4.9 Stars)

Alii Nui Sailing Charters

3 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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(26 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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(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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(6 Reviews, 4.8 Stars)

Frogman Charters

2 Activity Options

55' Power Catamaran

The charter boat company Boss Frog's is also known by the name Frogman Charters and it operates Molokini tours, whale watches, sunset sails and dinner cruises from it departure point of Maalaea Harbor. It's two main boats are the 55' power catamaran Malolo and the 55' power catamaran Quicksilver.
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(6 Reviews, 4.8 Stars)

Kauai Sea Tours

2 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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(6 Reviews, 4.8 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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(29 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.
More Info / Buy Now


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(10 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.
More Info / Buy Now


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(29 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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(4 Reviews, 4.8 Stars)

Sea Maui

2 Activity Options

Make reservations for a snorkel trip or sunset sail on the Sea Maui.

Sea Maui is a beautiful 51 foot power, sailing catamaran that departs out of Kaanapali Beach. They offer a trade-wind sail every afternoon, a sunset sail in the evening and snorkel trips in the morning. Food is specially provided by renowned Chef Joey Macadangdang the former corporate executive chef of Roy's Kitchen.
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(17 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)

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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(5 Reviews, 4.6 Stars)

Holokai Catamaran

2 Activity Options

Reserve a trip with the Holokai Catamaran

Go out on an adventure with Holokai Catamarans! Discover colorful tropical fish, green sea turtles, exotic coral reef and more of Hawaii's undersea life. Dolphins are also possibilities on this incredible adventure. Snorkeling in Hawaii is very fun and easy.
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(32 Reviews, 4.6 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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(7 Reviews, 4.6 Stars)

Paragon Sailing Charters

1 Activity Option

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.
More Info / Buy Now


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(19 Reviews, 4.5 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. You will have your choice of various tiers of dinner options varying between 7 course, 5 course and 3 course meals, all at varying prices. A smaller vessel, Starlite, seats only 149 passengers and provides dinner cruises as well. In the winter months the Star of Honolulu also provides whale watches.
More Info / Buy Now


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(9 Reviews, 4.3 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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(8 Reviews, 4.1 Stars)

Pacific Whale Foundation

6 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.
More Info / Buy Now


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(2 Reviews, 4 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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Aqua Zone

1 Activity Option

Oahu SCUBA Diving

Aqua Zone is a great option if you are looking to take-in some diving while visiting Oahu. One and two tank certified dives are available to visit the numerous 'boat and airplane wrecks' located off the southern and eastern shorelines. One and two tank introductory dives are also available at bountiful sea life locations as are daily snorkel tours.
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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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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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Privacy Charters

1 Activity Option

Sailing, Power Catamaran

Privacy features a large air conditioned cabin with a couch seating for 3 guests, table seating for four, or sit in either of the two captains chairs at the lower helm station. Further forward there is a large clean restroom on the port side, and stateroom with a queen size bed on starboard side.
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Royal Hawaiian Catamaran

1 Activity Option

52' Catamaran, 52' Catamaran - Sunset Excursions, 52' Sailing Catamaran, 52' Catamaran - Sunset Excu

One of the most beautiful catamarans to ever grace the waters off the coast of Waikiki is the 52' Rudy Choy designed custom cruising catamaran, the Royal Hawaiian. This famous boat builder built this specific boat with the expressed purpose of sailing Hawaiian waters. The boat is used for snorkel and sailing trips as well as private charters which can include dinner, sunset, star watching and whale watches.
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Tradewind Charter

1 Activity Option

Sail Oahu, Private Sail and Snorkeling, Private Sailing, Sunrise Sails, Snorkeling Tours and Memoria

Tradewind Charters specialize in private charters and can accommodate anywhere between just two to as many as twelve passengers on their 43 foot sailing yacht. Depending upon how many you may have in your party you just may be completely surprised in a favorable way by just how much money it will actually cost to charter a boat privately.
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Kona Style

1 Activity Option

Kona Style

Kona Style 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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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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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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Sea Monkey

1 Activity Option

Sea Monkey -  is a 31 foot Sea Ray Sundancer  Yacht

Sea Monkey is perfect for a private charter of up to 6 of your favorite people for a day or sunset on the water.
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Aloha Dolphin Tours

3 Activity Options

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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Epic Tours

1 Activity Option

Epic Tours - Hawaii

Epic Tours offers Jeep and 4 wheel drive SUV tours to hard to reach areas of the Big Island of Hawaii.
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Hula Kai

1 Activity Option

Hula Kai part of the Fair Wind

Join us aboard Fair Wind's sister vessel, Hula Kai.
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Sail Oahu

2 Activity Options

SV Shalimar is a 67 foot Mega Yacht

Experience Hawaii and the Pacific Ocean aboard your private yacht, Shalimar. The meaning of Shalimar in Sanskrit is "Home of Love on the Water".
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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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