Top Hawaii Sailing Trips

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Molokini Sail and Snorkel Adventure

5 star rating: Highly Recommended 148 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 ... 

Location: Maui, Hawaii
Duration: 5 hours

From USD $117.52

Na Pali Coast Kauai Snorkel and Sail

5 star rating: Highly Recommended 53 Reviews

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

Location: Eleele, Hawaii
Duration: 5 hours

From USD $169.61

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

5 star rating: Highly Recommended 53 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 ... 

Location: Eleele, Hawaii
Duration: 7 hours

From USD $229.34

Na Pali Snorkel Adventure

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

Location: Hanalei, Hawaii
Duration: 4 hours

From USD $212.27

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

5 star rating: Highly Recommended 41 Reviews

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

Location: Waikiki, Oahu
Duration: 5 hours 30 minutes

From USD $120.00

Leila Na Pali Sunset Dinner Sail

Sail the legendary Na Pali Coast aboard Leila, a 50-foot Kauai-made sailing catamaran and witness the beauty of 4000-foot cliffs, cascading waterfalls, sea ... 

Location: Eleele, Hawaii
Duration: 4 hours 30 minutes

From USD $137.60

Sail Maui Performance Sailing Charters

Sail Maui is proud to offer a destination snorkel sail to the exclusive island of Lana’i. Join us on Paragon to discover why the island has been named one of ... 

Location: Lahaina, Hawaii
Duration: 7 hours

From USD $195.00

Big Island Snorkel Cruise Along Kohala Coast

5 star rating: Highly Recommended 18 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 postcard-worthy ... 

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

From USD $157.54

Honolua Bay Snorkel Sail

5 star rating: Highly Recommended 1 Review

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 Maui’s ... 

Location: Lahaina, Hawaii
Duration: 5 hours

From USD $127.52

Whalewatch Sail Lahaina

4.5 star rating: Recommended 8 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 ... 

Location: Lahaina, Hawaii
Duration: 2 hours

From USD $57.01

Teralani Sunset Maui Cocktail Sail

4.5 star rating: Recommended 17 Reviews

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

Location: Maui, Hawaii
Duration: 2 hours

From USD $73.50

Afternoon Sail & Snorkel Captain Cook Monument at Kealakekua Bay

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava ... 

Location: Kahaluu-Keauhou, Hawaii
Duration: 3 hours

From USD $82.54

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 ... 

Location: Honolulu, Hawaii
Duration: 90 minutes

From USD $75.01

Deluxe Sail & Snorkel Captain Cook Monument at Kealakekua Bay

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain ... 

Location: Kahaluu-Keauhou, Hawaii
Duration: 4 hours 30 minutes

From USD $141.50

Aloha Sunset Sail

Enjoy a beautiful sunset like a kama’aina (local resident), as you set sail along Kauai’s sunny south shore listening to the classic mellow sounds of Hawaii’s ... 

Location: Eleele, Hawaii
Duration: 2 hours

From USD $90.67

Kepoikai Catamaran Charter

Charter your own catamaran cruise off the Waikiki Beach for your friends and family.  Ideal for special occasions, team bonding outings and family ... 

Location: Honolulu, Hawaii
Duration: 60 minutes

From USD $1,465.97

Kona-Kohala Coast Sunset Sail by Catamaran

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You ... 

Location: Waikoloa Village, Hawaii
Duration: 90 minutes

From USD $118.98

Whales and Cocktails Sail from Anaeho'omalu Bay

Combine unparalleled views of the Hawaiian coastline from a legendary sailing catamaran with the biggest guests of all -- the Humpback Whales -- and you have ... 

Location: Waikoloa Village, Hawaii
Duration: 90 minutes

From USD $138.25
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