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Oahu Sailing Trips

62 Results
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 …More

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
4.9 (218)
from
$62
Waikiki Friday Night Fireworks Cruise NYE SPECIAL 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 …More

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 hour Free Cancellation
4.7 (30)
from
$60
Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it ideal for guests who want to experience the ocean without getting wet. …More

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it ideal for guests who want to experience the ocean without getting wet....

1 hour Free Cancellation
5.0 (3)
from
$60
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Hawaii TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a …More

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

2 hours Free Cancellation
4.9 (1,015)
from
$55
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

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 …More

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 minutes Free Cancellation
5.0 (13)
from
$53
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

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 …More

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 hours Free Cancellation
4.7 (1,265)
from
$47
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 …More

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
5.0 (279)
from
$51
Waikiki Sunset Cruise: 2-Hour Catamaran & Swim Adventure in Oahu

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 …More

Likely to Sell Out
Likely to Sell Out

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
4.8 (600)
from
$47
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

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

Experience one Cool Hawaii'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
4.9 (1,799)
from
$50
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 …More

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
4.9 (264)
from
$50
Sunset sail Aboard Manakai Catamaran

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 …More

Likely to Sell Out
Likely to Sell Out

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 minutes Free Cancellation
5.0 (26)
from
$50
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 …More

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 minutes Free Cancellation
4.8 (26)
from
$48
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, …More

-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
4.9 (257)
from
$45
Waikiki Sunset Cruise from Oahu

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point …More

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point...

2 hours Free Cancellation
4.8 (76)
from
$45

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