Hawaii Sailing Trips

Honolua Snorkel Sail from Lahaina
Maui, USA

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way,...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
5.0 (58)
from
$180.92
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
Oahu, USA

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
Private Oahu Sunset Charter with Tasting and Drinks
Oahu, USA

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people...

120 to 150 minutesFree Cancellation
120 to 150 minutesFree Cancellation
120 to 150 minutes • Free Cancellation
5.0 (52)
from
$1,413.61
Kona Tradewind Catamaran Day Sail
Big Island of Hawaii, USA

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (49)
from
$80.10
Snorkel Sail Adventure off Ka'anapali Beach in Maui
Lahaina, USA

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky,...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (45)
from
$192.17
Maui Turtle Snorkel & Sail with Lunch & Open Bar
Maui, USA

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (40)
from
$122.40
Friday Night Firework Cruise in Waikiki
Oahu, USA

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)
from
$69.99
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
Oahu, USA

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 Heritage and Diamond Head Wildlife Sail
Oahu, USA

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This experience emphasizes relaxation, scenic views of Oʻahu’s south shore,...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (31)
from
$119
Morning Whale Watch: Lahaina Harbor
Likely to Sell Out
Likely to Sell Out
Maui, USA

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (29)
from
$100.22
Polynesian Canoe Day Sail
Oahu, USA

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
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
Maui, USA

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
5.0 (26)
from
$203.16
Private Catamaran Charter in Waikiki (1-6 Guests)
Likely to Sell Out
Likely to Sell Out
Oahu, USA

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)
from
$900
South Shore Open Sail from Kewalo Harbor Including Drinks
Oahu, USA

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 Turtle Snorkeling Tour 6 Activities + & Sunset Cruise
Honolulu, USA

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 (24)
from
$119
Sunset sail Aboard Manakai Catamaran
Likely to Sell Out
Likely to Sell Out
Oahu, USA

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (23)
from
$49.82

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