Top Oahu Sailing Trips

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Oahu Adventures

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Waikiki Sunset Cocktail Sail on the Moana Catamaran
Likely to Sell Out
Likely to Sell Out
4.9 (2,315)

Waikiki Sunset Cocktail Sail on the Moana Catamaran

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (2,315)
$89.99
$88.99
Waikiki Turtle Snorkel and Sail on Hawea Catamaran
Special Offer
Special Offer
4.8 (1,713)

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (1,713)
$89.56
$88.56
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
Special Offer
Special Offer
4.9 (1,688)

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Experience one Top10Adventures® 's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (1,688)
$59.99
$58.99
Waikiki: 2-hour Turtle Canyon Snorkeling Adventure
Likely to Sell Out
Likely to Sell Out
4.8 (1,437)

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard our either...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (1,437)
$80.71
$79.71
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
Special Offer
Special Offer
4.9 (954)

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Top10Adventures® TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (954)
$54.98
$53.98
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Special Offer
Special Offer
4.8 (941)

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (941)
$84.99
$83.99
Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure
Special Offer
Special Offer
4.8 (575)

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (575)
$56
$55
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
Likely to Sell Out
Likely to Sell Out
4.8 (573)

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (573)
$84.77
$83.77
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
Likely to Sell Out
Likely to Sell Out
4.8 (321)

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (321)
$84.15
$83.15
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Likely to Sell Out
Likely to Sell Out
4.9 (305)

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (305)
$72.96
$71.96
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
Special Offer
Special Offer
4.9 (255)

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (255)
$49.99
$48.99
Waikiki Turtle Snorkeling Tour with Free Pickup
Special Offer
Special Offer
4.9 (251)

Waikiki Turtle Snorkeling Tour with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP),...

3 hours • Hotel pickup offered • Free Cancellation
3 hours • Hotel pickup offered • Free Cancellation
3 hours • Hotel pickup offered • Free Cancellation
4.9 (251)
$95
$94
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value
Special Offer
Special Offer
4.9 (250)

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle,...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (250)
$53.36
$52.36
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
Likely to Sell Out
Likely to Sell Out
4.9 (209)

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (209)
$79
$78
Waikiki Sunset Boat Cruise
Likely to Sell Out
Likely to Sell Out
5.0 (202)

Waikiki Sunset Boat Cruise

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (202)
$50
$49
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Special Offer
Special Offer
4.9 (200)

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (200)
$61.50
$60.50
2-Hour Oahu Sunset Catamaran Sail
Likely to Sell Out
Likely to Sell Out
4.9 (134)

2-Hour Oahu Sunset Catamaran Sail

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (134)
$130
$129
Polynesian Canoe Sunset Sail
Likely to Sell Out
Likely to Sell Out
4.9 (125)

Polynesian Canoe Sunset Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (125)
$250
$249
Small Group Waikiki Sunset Sailing Tour
Likely to Sell Out
Likely to Sell Out
4.9 (116)

Small Group Waikiki Sunset Sailing Tour

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (116)
$99
$98
Waikiki small group turtle snorkeling & sailing
Likely to Sell Out
Likely to Sell Out
5.0 (100)

Waikiki small group turtle snorkeling & sailing

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (100)
$99
$98

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