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Top Oahu Sailing Trips

62 Results
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
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 (256)
from
$45
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
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
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

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

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

2 hours Free Cancellation
4.9 (1,795)
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
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
$51
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 (276)
from
$51
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
$53
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
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

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

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

2 hours Free Cancellation
4.9 (1,012)
from
$55
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
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
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 (217)
from
$62
Waikiki Sunset Cruise and Iconic Views with Swimming

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide …More

Likely to Sell Out
Likely to Sell Out

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide...

2 hours Free Cancellation
5.0 (4)
from
$65
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

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 …More

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 hours Free Cancellation
4.9 (223)
from
$67
Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden …More

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden...

2 hours Free Cancellation
4.6 (87)
from
$68
Glass Bottom Boat Fireworks and After Dark Reef Walker Cruise

Waikiki transforms into a vibrant spectacle on Friday nights, and the Friday Fireworks Cruise offers a unique vantage point to experience this magic. Departing from …More

Waikiki transforms into a vibrant spectacle on Friday nights, and the Friday Fireworks Cruise offers a unique vantage point to experience this magic. Departing from...

1 hour 30 minutes Free Cancellation
5.0 (3)
from
$69
Glass Bottom Boat Sunset and After Dark Reef Walker Cruise

Enjoy a stunning sunset cruise along the Waikiki coastline, where the heat softens and Diamond Head transforms into a silhouette against the vibrant sky. Departing …More

Enjoy a stunning sunset cruise along the Waikiki coastline, where the heat softens and Diamond Head transforms into a silhouette against the vibrant sky. Departing...

1 hour 30 minutes Free Cancellation
5.0 (1)
from
$69
Glass Bottom Boat Morning Coffee Cruise in Waikiki

Wake up to the serene beauty of Waikiki on the Morning Coffee Cruise, where you can savor locally roasted Ali’i Coffee Co. and fresh pastries …More

Wake up to the serene beauty of Waikiki on the Morning Coffee Cruise, where you can savor locally roasted Ali’i Coffee Co. and fresh pastries...

1 hour 30 minutes Free Cancellation
5.0 (3)
from
$69

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