Hawaii Sailing Trips

Hawaii Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: 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 89 Reviews

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

Location: Maui, Hawaii
Duration: 5 hours

From USD $117.52

Big Island Snorkel Cruise Along Kohala Coast

5 star rating: Highly Recommended 15 Reviews

Discover the best snorkeling off the Kohala Coast on this 3.5-hour Big Island snorkel cruise. Aboard a comfortable catamaran, admire Hawaii's ...  Read more

Location: Waikoloa Village, Hawaii
Duration: 3 hours 30 minutes

From USD $146.99

Luxury Catamaran Cruise from Oahu

4 star rating: Recommended 24 Reviews

Take a 2-hour sail through the waters of Hawaii on one of the fastest & most luxurious catamarans in Honolulu. Cruise the coast and open ...  Read more

Location: Waikiki, Oahu
Duration: 2 hours

From USD $69.00

Royal Feast Dinner Sail

5 star rating: Highly Recommended 6 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 ...  Read more

Location: Maalaea, Hawaii
Duration: 2 hours 30 minutes

From USD $179.00

Oahu Combo Adventure: Bike, Sail and Snorkel

5 star rating: Highly Recommended 29 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 $110.00

Teralani Sunset Maui Cocktail Sail

4.5 star rating: Recommended 7 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

Napali Snorkel Adventure

We invite you to climb aboard their Kauai-built rigid-hull inflatable “rafts” that will get you to the Napali Coast in record time! As we ...  Read more

Location: Hanalei, Hawaii
Duration: 4 hours

From USD $201.61

Catamaran Sailing and Snorkel Adventure on Kaneohe Bay

5 star rating: Highly Recommended 1 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

Honolua Bay Snorkel Sail

Come aboard Maui's newest luxury sailing catamaran and cruise along the beautiful Ka’anapali Coastline to the breathtaking waters of Honolua Bay, one of ...  Read more

Location: Lahaina, Hawaii
Duration: 6 hours

From USD $137.96

Sunset Sail

Part of the reason Maui has been voted the world’s #1 island year after year is due to our breathtaking sunsets! Sure you could just watch from the beach ...  Read more

Location: Kaanapali, Hawaii
Duration: 2 hours

From USD $50.00

Snorkel and Catamaran Sail

During the summer months, North Shore Catamaran Charters offers snorkeling and sailing tours in the beautiful waters of the North Shore of Oahu. Our Hawaii ...  Read more

Location: Haleiwa, Hawaii
Duration: Flexible

From USD $86.17

Romantic Sunset Sail

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 ...  Read more

Location: Maalaea, Hawaii
Duration: 2 hours

From USD $139.00

Memorial Day Luxury Catamaran Cruise from Oahu

Take a 2-hour sail through the waters of Hawaii on one of the fastest & most luxurious catamarans in Honolulu. Cruise the coast and open water alongside ...  Read more

Location: Waikiki, Oahu
Duration: 2 hours

From USD $79.00

Hawaiian Outrigger Canoe Sailing Adventure in Kane'ohe Bay

Experience this authentic Hawaiian outrigger canoe sailing adventure in beautiful Kane'ohe Bay. Explore the home of the "sunken island" Kane'ohe ...  Read more

Location: Kaneohe, Hawaii
Duration: 4 hours

From USD $185.09

Waikiki Panorama Sail

A scenic sail great for photos and sightseeing. The sail starts at the hip Kewalo-Kakaako district, down to the Ala Moana Beach shoreline, and finishes along ...  Read more

Location: Honolulu, Hawaii
Duration: 90 minutes

From USD $65.00

Napali Coast Kauai Snorkel and Sail

5 star rating: Highly Recommended 36 Reviews

Sail the majestic Napali Coast and witness its beauty with 4000’ cliffs, cascading waterfalls, sea caves, secluded beaches, dolphins, turtles and ...  Read more

Location: Eleele, Hawaii
Duration: 5 hours

From USD $149.00

Napali and Ni'ihau 'The Forbidden Island' Kauai Snorkel Cruise

5 star rating: Highly Recommended 43 Reviews

Discover the secrets of Hawaii’s legendary "Forbidden Island" of Niihau and the historical Napali Coast in one amazing day! You will voyage in ...  Read more

Location: Eleele, Hawaii
Duration: 7 hours

From USD $205.00

Kepoikai Catamaran Charter

Cruise off the Waikiki Beach with your friends and family!  Ideal for special get together.  Up to 37 passengers can come onboard. 

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
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Only Show: 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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