Hawaii Sailing Trips

Hawaii Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Catamaran Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Glass Bottom Boat Tours | Lunch Cruises | Night Cruises | Sailing Trips | Submarine Tours | Sunset Cruises

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Molokini Sail and Snorkel Adventure

5 star rating: Highly Recommended 121 Reviews

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or ...  Read more

Location: Maui, Hawaii
Duration: 5 hours

From USD $117.52

Na Pali Coast Kauai Snorkel and Sail

5 star rating: Highly Recommended 36 Reviews

Sail the majestic Na Pali Coast and witness its beauty with 4,000-ft cliffs, cascading waterfalls, sea caves, secluded beaches, dolphins, turtles and ...  Read more

Location: Eleele, Hawaii
Duration: 5 hours

From USD $158.94

Royal Feast Dinner Sail

5 star rating: Highly Recommended 10 Reviews

Come aboard Alii Nui, a luxurious sailing catamaran, and experience the Royal Feast Sunset Dinner Sail. Alii Nui and her expert crew treat you to a truly ...  Read more

Location: Maalaea, Hawaii
Duration: 2 hours 30 minutes

From USD $189.00

Oahu Combo Adventure: Bike, Sail and Snorkel

5 star rating: Highly Recommended 34 Reviews

Bike, sail & snorkel on Oahu on this exhilarating combo tour! Explore lush rainforest and sparkling ocean all in one day! Roundtrip Waikiki hotel ...  Read more

Location: Waikiki, Oahu
Duration: 5 hours 30 minutes

From USD $120.00

Na Pali and Ni'ihau The Forbidden Island Kauai Snorkel Cruise

5 star rating: Highly Recommended 44 Reviews

Sail past the soaring Na Pali sea cliffs on this 7-hour snorkeling adventure, and discover the secrets of the "Forbidden Island" when cruising the ...  Read more

Location: Eleele, Hawaii
Duration: 7 hours

From USD $205.00

Teralani Sunset Maui Cocktail Sail

4.5 star rating: Recommended 10 Reviews

This relaxing Maui cocktail cruise takes you between the islands of Lanai and Molokai, for a stunning picture-perfect sunset. Unwind with your ...  Read more

Location: Maui, Hawaii
Duration: 2 hours

From USD $71.50

Whalewatch Sail Lahaina

4.5 star rating: Recommended 7 Reviews

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum ...  Read more

Location: Lahaina, Hawaii
Duration: 2 hours

From USD $57.01

Romantic Sunset Sail

5 star rating: Highly Recommended 1 Review

Come aboard Alii Nui and get the Royal Treatment. Alii Nui and her expert crew will treat you to a truly memorable evening. Heavy appetizers and a full, open ...  Read more

Location: Maalaea, Hawaii
Duration: 2 hours

From USD $149.00

Sunset Cocktail Sail

5 star rating: Highly Recommended 4 Reviews

Enjoy a 2-hour sailing adventure. Part of the reason Maui has been voted the world’s #1 island year after year is due to the breathtaking sunsets. Sure you ...  Read more

Location: Kaanapali, Hawaii
Duration: 2 hours

From USD $75.88

Catamaran Sailing and Snorkel Adventure on Kaneohe Bay

5 star rating: Highly Recommended 2 Reviews

Sail and snorkel in Oahu's Kaneohe Bay during a 3-hour cruise aboard a small catamaran. Set sail from He’eia State Park with your expert guide and visit ...  Read more

Location: Oahu, Hawaii
Duration: 4 hours

From USD $171.99

Waikiki Panorama Sail

Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Beach and out towards Diamond Head crater. The cruise departs ...  Read more

Location: Honolulu, Hawaii
Duration: 90 minutes

From USD $70.66

Kepoikai Catamaran Charter

Cruise off the Waikiki Beach with your friends and family.  Ideal for special occasions.  The catamaran can accommodate up to 37 passengers.

Location: Honolulu, Hawaii
Duration: 60 minutes

From USD $1,047.12

Hawaii Pirate Ship Adventures

Enjoy fun for the whole family during our live pirate show aboard the Treasure Seeker!  Join our pirates in their search along the ...  Read more

Location: Honolulu, Hawaii
Duration: 90 minutes

From USD $75.70

Sail With the Whales from Anaeho'omalu Bay

This tour combines real coastal sailing on a legendary catamaran with the biggest party guests of all...the Humpback Whales! This tour also includes ...  Read more

Location: Waikoloa Village, Hawaii
Duration: 2 hours

From USD $106.10
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Only Show: Catamaran Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Glass Bottom Boat Tours | Lunch Cruises | Night Cruises | Sailing Trips | Submarine Tours | Sunset Cruises

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