Oahu Sailing Trips

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

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)
from
$196.63
South Shore Open Sail from Kewalo Harbor Including Drinks

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)
from
$47.50
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

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)
from
$90.01
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

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)
from
$93.46
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and a beautiful Hawaiian sunset in one unforgettable trip. Start...

4 hoursHotel pickup offeredFree Cancellation
4 hoursHotel pickup offeredFree Cancellation
4 hours • Hotel pickup offered • Free Cancellation
5.0 (25)
from
$119
Polynesian Canoe Day Sail

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)
from
$200
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

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)
from
$249.99
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (18)
from
$70
Polynesian Canoe Morning Sail

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)
from
$200
Diamond Head Sunset Sail

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)
from
$695
Waikiki Friday Night Fireworks Cruise

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring...

1 hourFree Cancellation
1 hourFree Cancellation
1 hour • Free Cancellation
4.7 (29)
from
$60
Private Catamaran Sunset Sail in Waikiki
Likely to Sell Out
Likely to Sell Out

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (11)
from
$900
Moana’s Luxury semi-private Sunset Cruise on Nalu

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (17)
from
$149.99
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar
Likely to Sell Out
Likely to Sell Out

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (13)
from
$53.36
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
Likely to Sell Out
Likely to Sell Out

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (14)
from
$1,150
2hr Luxury Private Sailing Catamaran for 7-12 People
Likely to Sell Out
Likely to Sell Out

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (3)
from
$1,495

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These answers are based on answers previously given to Cool Hawaii customers' questions.

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