Oahu Sailing Trips

Sunset sail Aboard Manakai Catamaran
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 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (23)
from
$49.82
Private Oahu Sunset Charter with Tasting and Drinks

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 (53)
from
$1,413.61
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...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (68)
from
$45
Waikiki Heritage and Diamond Head Wildlife Sail

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
$101.15
Friday Night Firework Cruise in Waikiki

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
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (210)
from
$79
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Likely to Sell Out
Likely to Sell Out

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (306)
from
$72.96
2-Hour Oahu Sunset Catamaran Sail
Likely to Sell Out
Likely to Sell Out

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu....

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (134)
from
$130
Small Group Waikiki Sunset Sailing Tour
Likely to Sell Out
Likely to Sell Out

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (116)
from
$99
Waikiki small group turtle snorkeling & sailing
Likely to Sell Out
Likely to Sell Out

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (103)
from
$99
Waikiki Turtle Snorkeling Tour with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP),...

3 hoursHotel pickup offeredFree Cancellation
3 hoursHotel pickup offeredFree Cancellation
3 hours • Hotel pickup offered • Free Cancellation
4.9 (279)
from
$89
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...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (255)
from
$49.99
Private Catamaran Charter in Waikiki (1-6 Guests)
Likely to Sell Out
Likely to Sell Out

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
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.7 (242)
from
$79
Waikiki private Day Tour and Sunset sail for couples
Likely to Sell Out
Likely to Sell Out

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (17)
from
$300
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
Likely to Sell Out
Likely to Sell Out

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.5 (37)
from
$101.96

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