Top Oahu Sailing Trips

Friday Night Firework Cruise in Waikiki
Special Offer
Special Offer

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline,...

1 hourFree Cancellation
1 hourFree Cancellation
1 hour • Free Cancellation
4.8 (34)
$69.99
$68.99

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
Likely to Sell Out
Likely to Sell Out

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (209)
$79
$78

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Likely to Sell Out
Likely to Sell Out

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 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (303)
$72.96
$71.96

Waikiki small group turtle snorkeling & sailing
Likely to Sell Out
Likely to Sell Out

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

2-Hour Oahu Sunset Catamaran Sail
Likely to Sell Out
Likely to Sell Out

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (133)
$130
$129

Waikiki Turtle Snorkeling Tour with Free Pickup
Special Offer
Special Offer

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 hoursHotel pickup offeredFree Cancellation
3 hoursHotel pickup offeredFree Cancellation
3 hours • Hotel pickup offered • Free Cancellation
4.9 (245)
$95
$94

Small Group Waikiki Sunset Sailing Tour
Likely to Sell Out
Likely to Sell Out

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (116)
$99
$98

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

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (255)
$49.99
$48.99

Private Catamaran Charter in Waikiki (1-6 Guests)
Likely to Sell Out
Likely to Sell Out

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (25)
$900
$899

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
Special Offer
Special Offer

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.7 (242)
$79
$78

Polynesian Canoe Day Sail
Likely to Sell Out
Likely to Sell Out

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

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (28)
$180
$179

Waikiki private Day Tour and Sunset sail for couples
Likely to Sell Out
Likely to Sell Out

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (17)
$300
$299

Polynesian Canoe Morning Sail
Likely to Sell Out
Likely to Sell Out

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

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (18)
$180
$179

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
Likely to Sell Out
Likely to Sell Out

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.4 (36)
$119.95
$118.95

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel
Special Offer
Special Offer

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above...

5 hours 30 minutesHotel pickup offeredFree Cancellation
5 hours 30 minutesHotel pickup offeredFree Cancellation
5 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.7 (67)
$196.63
$195.63

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Special Offer
Special Offer

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.6 (41)
$109.95
$108.95

South Shore Open Sail from Kewalo Harbor Including Drinks
Special Offer
Special Offer

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (25)
$47.50
$46.50

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
Special Offer
Special Offer

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night,...

1 hourFree Cancellation
1 hourFree Cancellation
1 hour • Free Cancellation
4.8 (58)
$90.01
$89.01

Diamond Head Sunset Sail
Special Offer
Special Offer

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (14)
$695
$694

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
Special Offer
Special Offer

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May,...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (34)
$249.99
$248.99

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