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Hawaii Sailing Charters

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There are tours in this Category that range in price from $29.90 to $4900.00

Sailing Charters

Sailing in Hawaii is a Way of Life.


Sailing in Hawaii whether it be on a Hawaii sailboat charter, a Hawaii Boat Tour or a Hawaii yacht charter is simply a way of life in the islands.


Keep in mind that the very first people to come to these islands came by virtue of a sailboat and so the sailing heritage runs deep in the waters surrounding Hawaii.


For that matter keep in mind that each and every one of the Hawaiian Islands is completely surrounded by water and so it is natural for Hawaii sailing to be such a big portion of the culture here.


Ocean water is one thing we have plenty of in Hawaii but the other ingredient necessary for a good sailing experience is wind, and we have been blessed here in Hawaii with plenty of that as well.


The trade winds will blow from the northeast in Hawaii about 300 days a year.


A typical day will have the wind blowing between 8 and 12 mph but it can get much windier than that.


Even on normal trade wind days wind gusts can be much greater than the average of that days wind velocity.


The trade winds will generally blow strongest in the afternoon and will begin to come up in the late morning hours so sailing conditions for most Hawaii Boat Tours are usually best in the afternoon if you are truly looking for a strong sail.


The Time of Year Can Affect Sailing in Hawaii.


Sailing in Hawaii during the winter months can be affected by the wind which can often reverse itself and come from the south.


We refer to these days as having Kona weather conditions.


This is the time of the year when we can have big storms and of course those days are not ideal for sailing but moderate Kona conditions can be just fine for Hawaii sailing adventures.


Where you are on an island can also play an important part in determining if it is a good place to launch from to enjoy some sailing fun.


The heaviest winds will most often be affecting the 'windward' sides of the islands which are the north and east coastlines.


These are the areas that will get wind first but quite often the wind will wrap around to the 'leeward' coastlines later in the day.


Many sailing charters prefer to leave from a location on the leeward side of an island and work their way up to the wind line as it wraps around.


This method allows for the beginning of a sail in calmer waters and also a return to calmer waters when coming back to port.


The Strongest Sailing Breezes in Hawaii are Usually in the Afternoon.


Stiff winds are not the only type of winds that are ideal for Hawaii sailing tours as late afternoon or Sunset Sails usually occur at a time when the wind has died down and what light wind is occurring is caused by the "temperature differential' caused by the cooling of the island mass.


These gentle conditions are ideal for romantic Sunset Sails and Dinner Cruises when too much wind would have an adverse affect upon the serving of cocktails and the enjoyment of Hawaiian "pupu's".


If you are looking to find wind for your sailing tour when you are visiting the islands the highest annual wind velocity is usually found in July however it should be mentioned that the wind speeds for each month are usually pretty consistent.


Rainfall might be something that would affect a beautiful Hawaii sailing charter and rain is something you could expect to be happening during the winter months.

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


Recent Reviews


Sailing Charters Sorted by Specific Tour


We sell tickets to 98 items in the category Sailing Charters in the state of Hawaii.

View the complete list below or use our Activity Finder to narrow down your options.

Displaying 98 of 98 Results

$104.90

From Waikiki, your professional nature guide will shuttle you by van to a tropical rain forest past Puowaina (Punchbowl Crater) to the top of Pu'u Ohia (Tantalus). Guests be outfitted with a bike and Bell…

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$157.90

From Waikiki, your professional nature guide will shuttle you by van to their own private 75 acre property in Manoa Valley. Guests will be issued trail snacks and a water bottle with optional rubber boots…

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$56.90

Meet at Kewalo Basin to board a 38 foot catamaran. Relax and unwind as you sail off the coast of Waikiki and Le'ahi (Diamond Head). Weather permitting, there will be optional swimming and snorkeling.…

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$147.00

The hospitality of the captain and crew on this Na Pali Coast Snorkel Tour is every bit as comforting as the stable ride guests encounter on this sea worthy ocean sailing catamaran. Expect dolphins, turtles…

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$200.00

Be one of the lucky few who have had the privilege of experiencing the crystal clear waters off the forbidden island of Niihau. This tour is similar to the NaPali trip but after going to NaPali they set…

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$159.00

Start your morning with a beautiful cruise along the NaPali Coast with amazing snorkeling and a hosted breakfast and lunch. All the gear is included. Explore Kauai's rugged NaPali Coast of spectacular…

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$89.00

Two hours of sailing into the sunset aboard a luxury catamaran with Kauai as a backdrop is a must do for every Hawaiian holiday. Enjoy a large shaded cabin area, comfortable cushioned seating and clean…

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$129.00

Explore Kauai's rugged Napali Coast where guests will see spectacular sea cliffs, enchanting waterfalls and timeless lava tubes. Enjoy a sunset with the history and legends of the ancient civilizations…

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$179.00

Start your morning with a beautiful cruise along the Na Pali Coast, where you'll see spectacular sea cliffs, enchanting waterfalls and timeless lava tubes. Enjoy the history and legends of the ancient…

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$159.00

Treat yourself to one of the new Star 65 foot luxury catamarans. Enjoy a large shaded cabin area, spacious, luxurious seating and opulent full size restrooms. Enjoy spectacular views of the rugged, pristine…

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$138.00

Tour along the awesome Napali Coastline. The special design of this vessel permits the Kahanu to get up close to view cascading waterfalls, lava tubes and sea caves. Snorkel Nu'alolo Kai (depending…

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$145.00

Guests of all levels come snorkeling aboard the Fair Wind II. This 4 hour cruise includes 2 hours of snorkeling at Captain Cooks Monument in Kealakekua Bay. All the snorkel gear and instruction are provided.…

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$89.00

Come and enjoy a scenic coastal cruise to Kealakekua Bay. Guests will enjoy 1 1/2 hours of snorkeling time, with snacks, beverages and a no-host bar during the last hour of the cruise. Set out on this…

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$110.90

Sail from West Maui's beautiful coastline. Daily destinations are based on the current weather conditions. They often go to either the Cliff House, Olowalu, Honolua Bay or Lanai. This large sailing…

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$89.00

See the scenic Ko'Olina Coast during the months of May through November on this West Oahu Ocean Playground afternoon adventure. Guests can often catch a dolphin sighting. Cruise and snorkel or upgrade…

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$69.00

Book this scenic sail and sightsee along the townside of Oahu, from the hip Kewalo-Kakaako district, down the Ala Moana Beach shoreline, along Waikiki and toward Diamond Head. Guests will often see turtles…

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$389.00

Hawaii Nautical takes you on an unparalleled yacht to experience the beauty and grandeur of the Kona coast and its most bejeweled underwater treasures at stunning snorkeling bays along the historic Kona…

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$2700.00

Sail to Kealakekua Bay and enjoy the scenic and historic Kona coastline. Snorkel Kealakekua's underwater marine sanctuary, in view of the Captain Cook Monument. See dolphins and turtles year round. During…

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$113.90

Three and a half hour afternoon scenic tour of Kauai's southwest shores, and the NaPali coast to see the sunset. This trip is on board the stable 65' catamaran Holo-Holo. Includes heavy appetizers,…

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$51.90

Enjoy your morning on Oahu and go on a snorkel on the Holokai Catamaran leaving from a Waikiki beach! Discover colorful tropical fish, green sea turtles, exotic coral reef and more marine life with this…

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$51.90

Go on a Waikiki snorkel at Noon on the newest boat in the Hawaiian Islands. Discover colorful tropical fish, green sea turtles, exotic coral reef and more of Hawaii's undersea life. Dolphins are also possibilities…

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$29.90

Choose this Waikiki coastline tour and experience an afternoon tradewind sail. This tour boasts having the newest boat in the Hawaiian Islands. A fun and high speed sailing adventure that travels along…

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$164.90

The 3 hour adventure begins with thorough instruction by our certified guides at He'eia State Park. Journey to Kaneohe Bay which is protected by Oahu's only Barrier Reef. Sailing sites are weather…

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$102.00 - $232.35

Join Hula Girl for a relaxing West Maui premiere snorkeling excursion on a beautiful sailing catamaran. In the spring and summer this tour usually goes to Honolua Bay, where there is an incredible variety…

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$1600.00

Choose the one of a kind beautiful sailing catamaran "Hula Girl" for your next private-charter excursion. Different seasons boast special attractions but all year Maui has wonderful things to see and experience…

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$115.90

Sunrise Dolphin and Turtle Reef Snorkel Experience. Board Island Princess and enjoy the beautiful scenery of the West coast of Oahu from the top. The top is also excellent to spot dolphins, and whale…

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$4900.00

Set sail from Maalaea Harbor and anchor along the southern shore in a remote, secluded area of Lanai. Snorkel, swim and sunbathe. After a delicious BBQ, watch the sunset as you're returning to Maui.…

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$2800.00

Set out for a half day of sailing and snorkeling aboard the luxurious Island Star. Search for dolphins and turtles, sail or just relax and sunbathe on the decks of this 57 foot luxury yacht.

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$1375.00

Sail away from the crowds aboard your own private yacht. Choose to experience performance sailing in the Pailolo Channel or leeward sailing in the 'Au'Au Channel. Snorkel with an in-water guide at a local…

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$825.00

Set sail in the calm leeward waters of Lahaina and discover the beauty of catching the wind. Relax and enjoy 360 degree views as the sun sets and lights up the islands of Maui, Molokai and Lanai. A private…

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$88.90

Three and one half hour snorkel trip to Pawai Bay, which is a protected area on private land that's located on the Kona Coast. Enjoy real sailing on Kona's only sailing catamaran. Snorkel amidst…

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$101.90

Weather permitting, you will head north looking for dolphins and get in the water for a once in a lifetime encounter. This is nothing like seeing them in captivity. You will be able to see them up close…

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$79.90

This tour usually departs around 5:00pm, arriving at the manta ray site in about 45 minutes. You can snorkel a bit before you watch an amazing sunset from the boat. Snacks, fresh island fruit, soda, juice…

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$84.90

Join us for a deluxe morning snorkel trip to Pawai Bay, a protected area on private land, located on the Kona Coast. Enjoy real sailing on Kona's only sailing catamaran. Snorkel and see rainbow colored…

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$133.90

Enjoy a 5 hour morning adventure to the NaPali coast on an exciting sailing catamaran. This tour teems swimming, a chance to snorkel, great food and hearing about the history and legends of the area together…

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$102.90

Experience an amazing 4 hour cruise along Kauai's spectacular coast with a 3 course dinner and a romantic Hawaiian sunset. As the afternoon light brings special magic to NaPali hear the history and legends…

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$133.90

Imagine 5 hours to enjoy the sea on this deluxe afternoon snorkel and dinner cruise. Sunset is a magical time and towards the end of your tour the scenery will show off it's color palette. Listen while…

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$33.90

The trade-winds provide the backdrop as Maita`i surfs the swells off Waikiki. The wind and waves rush by on this unique hour and a half sail. Book the Tradewind Sail and make it park of your Oahu adventure today!

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$79.90

Enjoy a nice 2 hour afternoon sail along the south shore and see the beautiful views of the lush Ko'olau Mountains, Diamond Head, Waikiki and Honolulu sky lines. Spinner Dolphins are often seen and…

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$97.90

Sail out to Turtle Canyon along the south shores of Honolulu and Waikiki and snorkel off the boat in the warm water where you will see turtles and a variety of fish. On your trip back, keep an eye open…

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$185.00

This boat conveniently departs from the beach in front of the Makena Beach and Golf Resort, making it ideal for those staying in the Wailea and Makena area. Come aboard the Kai Kanani II as it departs…

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$1300.00

Snorkel like a pro while you see turtles, tropical fish endemic to Hawaii, and enjoy some of the Pacific's best dive sights. Shadowfax is equipped with the very best snorkel and safety gear. and offers…

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$99.00 - $650.00

With NOAA's Hawaiian Islands Humpback Whale National Marine Sanctuary located right in Kihei, whale watching is the best in the world in Maalaea Bay. Every year the same whale community commutes from Alaska…

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$325.00

Make your dreams come true by customizing your trip aboard Shadowfax. Your crew with 30 years experience in Hawaiian waters can help you have the time of your life. Go sailing, snorkeling or enjoy a beautiful,…

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$99.00

Enjoy two hours of tradewind sailing on Shadowfax. Maui's tradewinds offer great sailing all around Maui County, this is the perfect vessel to experience the freedom of moving on the wind along the water.…

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$109.00

Book this Sunset whale watch and enjoy 2.5 hours on the water at a spectacular time of day. Every year the same whale community commutes from Alaska to birth their calves around Maui in our warm, safe…

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$91.90

Enjoy a morning of sunshine, motor out to a secluded snorkel site along the Kohala Coast, receive a short briefing and get geared up, descend on Winona's easy access "Stairway to the Sea" directly into…

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$110.00

Choose this sailing adventure aboard the sleek Ho'o Nanea for a 4 hour snorkel adventure! Guests are provided all snorkel gear and instruction and will snorkel in the clear tropical water near famous…

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$60.00

Cruise along the picturesque North Shore to the Waimea Bay area. Feel free to bring your own alcoholic beverages.For guests needing assistance with a walker please inform agent at time of reservation so that you can be properly accommodated.

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$80.00

The North Shore of Oahu has more whale sightings than any other location on Oahu. Annually there can be over 700 sightings. There have even been two double breaches in the Haleiwa Harbor Channel documented.…

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$60.00

This tour will set sail in search of turtles aboard the sleek Ho'o Nanea, and in the summer months when ocean conditions permit snorkel in the clear tropical water near famous Waimea Bay. Guests will…

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$60.00

Sunset, stargazing and full moon cruise. These trips are usually available two nights out of each month, most of the year. Tour is run in lieu of the traditional sunset cruise. Dates are determined by…

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$80.00

Get ready for an amazing 3 hour sail and snorkel adventure aboard the sleek Ho'o Nanea. Guests are provided all snorkel gear and instruction! Expert crew members will show you tropical fish and fascinating…

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$105.89

Reserve the Honolua Bay Snorkel Sail and go aboard Ocean Spirit, a luxury sailing catamaran, and cruise along the beautiful Ka'anapali Coastline. A continental breakfast and lunch with a colorful souvenir…

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$109.90

Let the wind catch the sails and you are off to Maui';s most visually stimulating snorkel destination. This five hour morning snorkel trip features a continental breakfast, buffet lunch, snacks, beer,…

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$64.90

Sailing out of Maalaea Harbor provides some of the best speed sailing in the world with flat water and stiff breezes. We often reach speeds in excess of 20 knots. This three hour trip features two hours…

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$174.90

The adventure begins in Lahaina Harbor where we set sail across the Au'au' channel to Lana'i. A continental breakfast featuring some of Hawaii's tastiest tropical fruit is served as you enjoy the panoramic…

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$133.90

This is a unique tour with no pre-planned destination. After about an hour's sail it's the Captain's choice of where your destination and the best snorkel spot of the day will be. Spend some time exploring…

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$67.50

Maui is a special place to see the humpback whales. Feel the wind and "sail" with these gentle giants. Each year they migrate from Alaska to make Hawaii their home. The Au'au channel off the coast of Maui…

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$129.00

Enjoy an all-you-can-eat lunch at sea, and snorkel in Hawaii's beautiful azure waters at the Turtle Canyon. Our eco-conscious cruise lets you see whales (in season, late November through April), fish,…

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$39.00

Set sail off Oahu's coast on, the Hilton Adventure Sail, a morning expedition to Diamond Head. For those doing a lot in one day this tour is only an hour and makes room for other adventures or events you…

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$89.00

There's nothing like a Hawaiian sunset and nothing beats seeing a sunset from sea. During this trip you will enjoy a scenic cruise from the Hilton Pier south towards Diamond Head. Normally the captain…

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$149.00

Set sail from Waikiki Beach onboard the 54 foot catamaran Spirit of Aloha to view the fireworks and eat dinner at sea. During the cruise you will be served an array of gourmet, fresh selections. The menu…

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$106.90

Choose this Pride Premier Morning Molokini Snorkel for a deluxe two destination snorkel, snuba and scuba excursion featuring an island style continental breakfast and a hot BBQ lunch! A friendly crew will…

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$450.00 - $3175.00

This wonderful Power Flybridge catamaran is an ideal private charter boat for small groups or a family searching for a moderately priced excursion with the luxury of a private charter. Go sailing, snorkeling,…

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$450.00

Explore the island of Lanai's world famous dive sites. Choose from up to forty different dive sites from Cathedrals to Shark Fin Rock. Spinner dolphins are common sightings around the island of Lanai.…

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$174.90

The destination of this trip is usually at Turtle Canyon where you can snorkel in 20 feet of water for 35 to 45 minutes over beautiful tropical reefs filled with many varieties of fish and sea creatures.…

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$1650.00 - $4500.00

Choose what you like to do and book this private boat tour for two, three, four or six hour cruises. Food and beverages are provided and alcoholic beverages are available for the adults. Equipment for…

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$2250.00

On this Private Sunset in Paradise Sail feel the sea spray and look for dolphins on the bow while the sun sets slowly into the majestic Pacific Ocean! Relax Hawaiian style, enjoy tasty "Pupu's" (Hawaiian…

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$2250.00

Choose this Private Friday Night Firework Sail and get the Sunset and a Fireworks display! Guests can look for dolphins or whales on the bow while the sun sets slowly into the majestic Pacific Ocean!…

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$1200.00

Reserve a private charter to say farewell and pay your last respects to a loved one aboard a luxury sailing yacht. Create a serene and reflective mood whether you choose a beautiful sunrise or want to…

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$98.90

This 4 hour excursion includes two hours of sailing and two hours of snorkeling. A knowledgeable crew will guide you through the pristine reef along the Lanai and Maui shores and afterwards you will enjoy…

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$61.90

Enjoy two hours of sailing off the majestic West Maui Coast, and enjoy a beautiful sunset at sea while you sit back, relax and let us do all the work. Whale watching when in season, December-May.

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$1200.00 - $2100.00

Design your own custom charter for you and your private group.

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$52.90

Enjoy two hours of real sailing. This voyage will take you along the West Maui coastline. Take in the sun, wind and salt spray as the island trade winds fill the sails. Whale watching is also available when in season.

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$52.90

Relax and enjoy the trade-winds as you sail silently along in Maui's crystal clear water, on a wind-powered sailing vessel, no engine noise so you can enjoy the quiet of the world.

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$124.90 - $1000.00

This is the only catamaran departing from Kaanapali Beach that will take you to Lanai for a snorkel, sailing adventure. In search of West Maui's best snorkel sites, you set off for the island of Lanai…

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$105.90 - $1000.00

Depart from Kaanapali beach and set off in search of West Maui's best snorkel sites for the day, based on current water conditions. Enjoy your breakfast and coffee that has been prepared by Chef Joey and…

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$121.90

Sail for about 45 minutes along the beautiful Kona coast to historic Kealakekua Bay. Your captain will select the best snorkeling sites for the day and your friendly and professional crew members provide…

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$107.90

Enjoy a beautiful Hawaiian sunset aboard the Hokulani, as you sail from Keauhou Bay into the setting sun (sailing times vary according to sunset). After sunset we drop sail and head for the World Famous…

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$70.90

Your captain will select the best snorkeling site of the day, in Kealakekua Bay, and your friendly and professional crew members will provide site briefings and historical facts along with snorkel tips…

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$468.90

Your loved one's ashes can be scattered on the smooth ocean waters of Hawaii by your family and friends or by the captain, during a beautiful sunrise or sunset. Pay your last respects to a loved one aboard…

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$570.90 - $1133.90

Individuals, families and small groups or companies can sport fish in privacy aboard our comfortable vessel. A variety of reef fish are caught while anchoring or drift fishing over reefs on a reef fishing…

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$468.90

This sail is ideal for the romantic couple who is up at dawn due to time zone changes. Enjoy the brilliant colors of a sunrise at sea from the deck of the Love Boat. Enjoy complimentary mimosas (champagne…

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$704.90 - $823.90

This sail is perfect for visitors with a desire for real sailing in a private setting. Departure from Honolulu permits guests to enjoy the beauty and excitement of blue water sailing year round, and while…

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$468.90

Develop your basic skills and knowledge to further your sailing dreams. Through private lessons and hands-on instruction, sailors quickly advance, developing the confidence and competence to safely operate…

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$468.90 - $704.90

Between December and May every year, humpback whales visit the Hawaiian Islands. These whales reach lengths of 35 to 50 feet and weigh up to 50 tons. These intelligent visitors return annually to deliver…

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$218.42

This trip is what Trilogy is best known for. Depart from Lahaina Harbor at around 10:00 am (occasionally there is a sunrise departure at 6:30am). Start your day with an island style breakfast of Mama Coon's…

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$138.19

Explore the crystal clear waters of Molokini Crater and Maui's coastline, the home of the Hawaii honu (sea turtle). As you sail from Ma'alaea Harbor, enjoy Mom Coon's home made cinnamon rolls…

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$133.73

Snorkel, swim and discover snuba from Honolua Bay to Olowalu with views of Moloka'i, Lana'i and the West Maui Mountains. Snorkel (weather permitting) at an alternate site may be chosen if undesirable…

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$60.62

Delight in this amazing two hour whale watch leaving from Kaanapali. You start off a little wet as you load directly from the beach through the surf onto the boat! Aboard this catamaran Trilogy naturalist…

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$88.26

Experience a idyllic sunset sail exploring the West Maui coastline surrounding Kaanapali. Enjoy Maui's legendary kamakani (wind) with Trilogy. They really put the sails up then while you take it all in…

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$60.62

Leave from Maalaea for this amazing two hour whale watch! Trilogy is dedicated to sharing accurate information about the endangered humpback whale and its habitat with guests through on-board naturalists.…

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$60.62

Enjoy this amazing two hour whale watch leaving from Lahaina! Trilogy is dedicated to sharing accurate information about the endangered humpback whale and its habitat with guests through on-board naturalists.…

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$132.84 - $132.84

Experience fine dining with an unbeatable view! Tables are set for intimacy and comfort. Your evening begins with cocktails and sailing along the pali sea cliffs. After mooring in a protected cove, your…

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$124.81

Sail with Trilogy to "Maui's Mother Reef" and experience one of the largest turtle cleaning stations in Hawaii! Relax and enjoy a later departure, a continental breakfast along the way, before arriving…

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$132.84 - $132.84

Experience fine dining with an unbeatable view! Tables are set for intimacy and comfort. Your evening begins with cocktails and sailing along the west side of Maui. After mooring in a protected cove, enjoy…

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$1050.00

Join Wahine Charters for your customized private charter. The crew of Wahine Charters loves to fish, swim with dolphins, snorkel coral reefs and help others discover what the oceans of Hawaii have to offer.…

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Sailing Charters Sorted by Company

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(11 Reviews, 5 Stars)

North Shore Catamaran Charters

6 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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(9 Reviews, 5 Stars)

Blue Dolphin Charters

2 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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(9 Reviews, 5 Stars)

Maui Ocean Charters

5 Activity Options

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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(7 Reviews, 5 Stars)

Port Waikiki Cruises

4 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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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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(4 Reviews, 5 Stars)

Bike Hawaii

3 Activity Options

Bike Adventures, Mountain Bike Tours

The company 'Bike Hawaii' deals with much more than just bike rides. Over their long history they have evolved to include hiking tours and kayaking trips as well as snorkeling and sailing adventures. Common ground for all these tours is a desire to take the island visitor to out of the way places and provide an ecological perspective.
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(3 Reviews, 5 Stars)

Tradewind Charter

6 Activity Options

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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(2 Reviews, 5 Stars)

Catamaran Kahanu

1 Activity Option

36' Sailing Catamaran, 36' double hull Hawaiian Catamaran

Catamaran Kahanu is a boat tour company that offers tours of the spectacular NaPali Coastline on Kauai's North Shore and also offers dinner cruises and whale watches. With a maximum capacity of only eighteen passengers these tours are very personalized and your captain and crew are of Hawaiian ancestry and have been lifelong residents of Kauai.
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(2 Reviews, 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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(1 Review, 5 Stars)

Iruka Hawaii

1 Activity Option

Dolphin Snorkel Tours, Manta Tour, Whale Watch

Iruka Hawaii offers snorkel and dolphin watch tours off the coasts of the two islands in Hawaii that provide the very best venue for observing dolphins, the Waianae Coast of Oahu and the Kona Coast of the Big Island of Hawaii.
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(1 Review, 5 Stars)

Island Star

2 Activity Options

57' Sailing Yacht - Private charter only

The Island Star is a sail boat that is in a category of its own. This 57' sailing Columbia Yacht can accommodate as many a twenty guests and is used exclusively for private charters.
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(1 Review, 5 Stars)

Sea Paradise

3 Activity Options

Snorkel - 50' Catamran

Sea Paradise is a 50 foot sailing catamaran, the Hokuhele, which explores beautiful locations along the Kona coastline. Trips depart from Keauhou Bay heading down the coastline towards the historic marine preserve, Kealakekua Bay. Dolphins or even whales when in season will often become a major focal point of these trips. Evening tours are also available to see the amazing giant Manta Rays.
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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)

Holokai Catamaran

3 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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(29 Reviews, 4.9 Stars)

Paragon Sailing Charters

5 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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(21 Reviews, 4.9 Stars)

Scotch Mist Sailing Charters

5 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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(8 Reviews, 4.9 Stars)

Fair Wind Charters

2 Activity Options

50' Sailing Catamaran, 55' Teknicraft Catamaran

Well established as a tour boat company on the Kona Coast of the Big Island, Fair Winds Charters has two beautiful and distinctive boats that offer a complement of tours which include snorkel tours to Kealakekua Bay and evening Manta Ray excursions. Also included as a part of the day snorkels are SNUBA diving and the new sea rocket underwater propulsion vehicles.
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(48 Reviews, 4.8 Stars)

Trilogy Excursions

10 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.
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(12 Reviews, 4.8 Stars)

Kauai Sea Tours

3 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)

Hula Girl

2 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.
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(45 Reviews, 4.8 Stars)

Captain Andy's Expedition

5 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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(13 Reviews, 4.8 Stars)

Kamanu Charters Inc.

4 Activity Options

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, 4.8 Stars)

Holo-Holo Charters

1 Activity Option

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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(8 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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(3 Reviews, 4.7 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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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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Holokai Kayak Adventure

1 Activity Option

Kayak off Kaneohe

Blessed with some of the most calm, clear and beautiful snorkeling waters in the state Kaneohe Bay is the location that is visited by Holokai Kayak and Snorkel Adventure. You will enjoy the bay and the sea life but will also get a chance to kayak out to the film location of Gilligan's Island. These guided kayak tours are wonderful but if you would like to rent a kayak on your own, that can be arranged as well.
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Maita'i Catamaran

1 Activity Option

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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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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Pacific Whale Foundation

1 Activity Option

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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Privacy Charters

2 Activity Options

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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Wahine Charters

1 Activity Option

Dolphin Excursions, Whale Watch Tour - Wahine Charters, Snorkeling and Manta Ray trips from Honokoha

Wicked Wahine Charters operates a series of boat tours out of Kailua-Kona on the Big Island. Their 29' custom power vessel can easily traverse the 12 miles of coastline between Honokohau Harbor and the Captain Cook Monument while snorkeling and dolphin watching on the way, or it can take you out on a night time Manta Ray adventure or whale watching.
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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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Sail Oahu

4 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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Top Activities
Customer Favorite Tours Based on Reviews