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Top Hawaii Sailing Trips

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure
Likely to Sell Out
Likely to Sell Out
Oahu, USA

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (1,429)
from
$85.71

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Oahu, USA

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 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (941)
from
$89.99

Waikiki Sunset Cocktail Sail on the Moana Catamaran
Likely to Sell Out
Likely to Sell Out
Oahu, USA

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (2,304)
from
$94.99

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

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (564)
from
$61

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed
Honolulu, USA

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and...

2 to 3 hoursHotel pickup offeredFree Cancellation
2 to 3 hoursHotel pickup offeredFree Cancellation
2 to 3 hours • Hotel pickup offered • Free Cancellation
4.7 (2,089)
from
$104

Kauai: Leila Na Pali Sunset Dinner Sail
Likely to Sell Out
Likely to Sell Out
Kauai, USA

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa...

4 to 5 hoursFree Cancellation
4 to 5 hoursFree Cancellation
4 to 5 hours • Free Cancellation
4.8 (548)
from
$273.82

Waikoloa Signature Catamaran Sunset Sail
Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers...

90 to 120 minutesFree Cancellation
90 to 120 minutesFree Cancellation
90 to 120 minutes • Free Cancellation
4.8 (407)
from
$166.50

Waikiki Turtle Snorkel and Sail on Hawea Catamaran
Oahu, USA

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 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (1,705)
from
$94.56

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

-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 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (250)
from
$58.36

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
Likely to Sell Out
Likely to Sell Out
Oahu, USA

-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 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (567)
from
$89.77

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
Oahu, USA

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

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (1,659)
from
$51.99

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
Big Island of Hawaii, USA

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (707)
from
$196.50

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady
Kauai, USA

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
4.8 (1,528)
from
$232.86

Snorkel with Manta Rays Guaranteed
Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (736)
from
$149.07

Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu
Oahu, USA

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.7 (1,265)
from
$58.31

Kona Signature Catamaran Sunset Sail
Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (292)
from
$116.50

Waikiki Sunset Boat Cruise
Likely to Sell Out
Likely to Sell Out
Oahu, USA

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 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (188)
from
$55

Day's End Cocktail Sunset Sail
Likely to Sell Out
Likely to Sell Out
Maui, USA

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (85)
from
$166.50

Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Maui, USA

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
4.8 (816)
from
$223.41

Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Oahu, USA

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 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (197)
from
$66.50

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