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Sailing charters and tours in Hawaii.

Hawaii Sailing Charters

There are products in this Category that range in price from $29.90 to $4200.00

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 sail boat 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 effecting 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.


We sell tickets to 86 items in the category Sailing Charters in the state of Hawaii.

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Displaying 86 of 86 Results

$59.00
(7 Reviews, 5 Stars)

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…

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$69.00
(6 Reviews, 5 Stars)

Enjoy two hours of sailing off the majestic West Maui Coast, while enjoying one of our complimentary beverages-beer, wine, soft drink, or bottled water-while you sit back, relax and let us do all the work.…

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$171.90
(5 Reviews, 5 Stars)

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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$131.90
(5 Reviews, 5 Stars)

This 5 hour morning trip to the NaPali coast includes it all. Thrill to the sight of playful spinner dolphins, sea turtles and the spectacular beauty of NaPali. Your friendly and attentive crew share history…

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$159.00
(5 Reviews, 5 Stars)

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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$147.00
(4 Reviews, 5 Stars)

You will find the hospitality of the captain and crew every bit as comforting as the stable ride you'll encounter on this sea worthy ocean sailing catamaran. Expect dolphins, turtles and whales (in…

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$101.90
(4 Reviews, 5 Stars)

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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$64.90
(4 Reviews, 5 Stars)

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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$44.90
(4 Reviews, 5 Stars)

Sail out to Waikiki's best diving spots, where you can swim, snorkel and explore the reef. Afterwards, have lunch aboard the boat, then kick back, listen to tunes, soak up the sun and enjoy an exhilarating…

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$101.90
(3 Reviews, 5 Stars)

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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$135.00
(3 Reviews, 5 Stars)

Go snorkeling aboard the Fair Wind II. This 4 hour cruise includes 2 hours of snorkeling at Captain Cooks Monument in Kealakekua Bay. Snorkel gear and instruction are provided. In addition, the boat…

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$101.90
(3 Reviews, 5 Stars)

A 3.5 to 4 hour cruise along Kauai's spectacular coast as the afternoon light brings a special magic to NaPali. Hear the history and legends from the crew and experience sightseeing, dolphin watching…

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$79.90
(3 Reviews, 5 Stars)

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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$79.00
(3 Reviews, 5 Stars)

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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$88.90
(3 Reviews, 5 Stars)

Set sail for an adventure aboard the sleek Ho'o Nanea and snorkel in the clear tropical water near famous Waimea Bay. Our expert crew will show you tropical fish and fascinating reef formations. A…

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$94.90
(3 Reviews, 5 Stars)

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), where you'll be outfitted with…

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$71.90
(3 Reviews, 5 Stars)

The North Shore of Oahu has more whale sightings than any other location on Oahu. Last season there were over 700 sightings and two double breaches in the Haleiwa Harbor Channel. Between December and…

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$55.90
(3 Reviews, 5 Stars)

Cruise along the picturesque North Shore to the Waimea Bay area. Feel free to bring your own alcoholic beverages.

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$99.00
(2 Reviews, 5 Stars)

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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$89.90
(2 Reviews, 5 Stars)

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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$704.90
(1 Review, 5 Stars)

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, while…

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$750.00
(1 Review, 5 Stars)

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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$185.00
(1 Review, 5 Stars)

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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$131.90
(1 Review, 5 Stars)

This 5 hour deluxe afternoon snorkel and dinner cruise is available from the middle of May to the middle of September. The afternoon light brings a special magic to Na Pali. Listen while the crew share…

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$129.90
(1 Review, 5 Stars)

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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$129.00 - $129.00
(1 Review, 5 Stars)

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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$69.90
(1 Review, 5 Stars)

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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$51.90
(1 Review, 5 Stars)

This snorkel tour is ideal for those on vacation that want a later start to their day. Snorkeling in Hawaii is very fun and easy. If you've never snorkeled before, no worries, it is not difficult!! We…

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$205.00
(8 Reviews, 4.9 Stars)

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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$129.00
(9 Reviews, 4.8 Stars)

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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$129.90
(9 Reviews, 4.8 Stars)

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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$151.90
(4 Reviews, 4.8 Stars)

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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$106.90
(4 Reviews, 4.8 Stars)

Explore Kauai's rugged Napali Coast where you'll 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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$91.91
(3 Reviews, 4.7 Stars)

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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$105.90
(8 Reviews, 4.6 Stars)

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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$79.90
(4 Reviews, 4.5 Stars)

Get out on the ocean for a sunset sail. Take in the panoramic sunset views and see the light changing colors on the mountains behind you. This trip includes two hours of real sailing. There will also…

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$1200.00 - $1500.00
(2 Reviews, 4.5 Stars)

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

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$79.00
(2 Reviews, 4.5 Stars)

Come and enjoy a scenic coastal cruise to Kealakekua Bay, keep your eye out for spinner dolphins, they often come by the boat to entertain the passengers. Set out on a special afternoon cruise and enjoy…

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$129.90
(4 Reviews, 4.3 Stars)

Start your morning with a beautiful cruise along the NaPali Coast and snorkel. Explore Kauai's rugged NaPali Coast where you'll see spectacular sea cliffs, enchanting waterfalls and timeless…

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$94.90
(6 Reviews, 4.2 Stars)

This deluxe two destination snorkel, snuba and scuba excursion features an island style continental breakfast in route to Molokini Crater and a hot BBQ lunch. A friendly crew will give you expert instructions…

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$119.00
(1 Review, 3 Stars)

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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$4200.00

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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$450.00 - $2250.00

This wonderful sailing power catamaran is ideal for small groups or a family searching for a moderately priced excursion with the luxury of a private charter. Go sailing, snorkeling, cruising the coastline…

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$2400.00

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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$124.90 - $1000.00

This is the only catamaran departing from Kaanapali Beach that will take you to Lanai for a snorkel, sailing adventure. As you set off for the island of Lanai you will be offered breakfast and coffee prepared…

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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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$468.90 - $1215.90

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

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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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$1250.00

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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$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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$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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$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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$450.00

Cruise the north shore of Molokai, where the world's tallest sea cliff with spectacular cascading waterfalls will amaze you, or visit the secluded coves along east Molokai's tropical shoreline.…

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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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$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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$465.90

Your whale watch is located just minutes from the Kohala Coast resorts, and adjacent to the Hawaiian Islands Humpback Whale National Marine Sanctuary. These conservation waters protect humpback whales…

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$304.90

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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$159.90

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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$134.90

Tour along the awesome Na Pali Coastline. The special design of this vessel permits us to get up close to view cascading waterfalls, lava tubes and sea caves. Snorkel Nu'alolo Kai, ocean conditions…

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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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$135.00

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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$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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$108.90

Come aboard Ocean Spirit, a luxury sailing catamaran, and cruise along the beautiful Ka'anapali Coastline to the breathtaking waters of Honolua Bay, one of Maui's most popular snorkel spots. Enjoy a leisurely…

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$109.00

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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$131.90

Board the Island Princess, a sturdy catamaran, and begin to cruise Oahu's Waianae coastline to search for and swim with dolphins. We will perform chanting for safety in the traditional Hawaiian style.…

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$84.90

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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$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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$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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$64.06

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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$79.00

See the scenic Ko Olina Coast, which usually includes at least one dolphin sighting. Cruise and snorkel, or upgrade to the stand up paddle board package. During whale watching season from December through…

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$139.90

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

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$101.90

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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$59.00

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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$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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$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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$49.00

Set sail on an expedition to Diamond Head. Along the way you'll have the opportunity to take in the sights and delights of Oahu's beautiful natural and city scenery. See marine wildlife in their…

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$56.90 - $63.90

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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$51.90

Go snorkeling 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 on this…

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$32.47

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.

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$51.90

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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$29.90

Come and experience an afternoon tradewind sail on the newest boat in the Hawaiian Islands. Enjoy a fun and high speed sailing adventure along Oahu's beautiful coastline with incredible views of Waikiki…

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$300.00

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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$225.00

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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$101.90

Enjoy 2.5 hours on the water at sunset time and go whale watching. Includes hot and cold pupus. Bring your own alcoholic beverages. Every year the same whale community commutes from Alaska to birth their…

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