Hawaii Sailing Trips

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Hawaii Activities

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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, …More

Oahu, USA
4.8 (35)

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 hour • Free Cancellation
4.8 (35)
from
$70
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from …More

Oahu, USA
4.9 (18)

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from...

2 hours • Free Cancellation
4.9 (18)
from
$70
2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and …More

Oahu, USA
5.0 (3)

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and...

2 hours • Free Cancellation
5.0 (3)
from
$70
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
Honolulu, USA
4.9 (215)

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...

2 hours • Free Cancellation
4.9 (215)
from
$71
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

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 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (316)

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

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 minutes • Free Cancellation
4.9 (316)
from
$73
Waikiki Fireworks Cocktail Cruise

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to …More

Oahu, USA
4.6 (10)

Waikiki Fireworks Cocktail Cruise

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to...

1 hour 30 minutes • Free Cancellation
4.6 (10)
from
$77
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 …More

Honolulu, USA
4.7 (242)

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 hours • Free Cancellation
4.7 (242)
from
$79
Waikiki 2 hour Turtle Canyon Snorkeling Adventure

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 the either …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.8 (1,462)

Waikiki 2 hour Turtle Canyon Snorkeling Adventure

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 the either...

2 hours • Free Cancellation
4.8 (1,462)
from
$81
North Shore Catamaran Charters

Perfect for families, couples, and ocean lovers seeking an unforgettable Hawaiian experience. Witness the majestic whales and stunning sunsets on the North Shore of Oahu. …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (1)

North Shore Catamaran Charters

Perfect for families, couples, and ocean lovers seeking an unforgettable Hawaiian experience. Witness the majestic whales and stunning sunsets on the North Shore of Oahu....

1 day 2 hours • Free Cancellation
5.0 (1)
from
$84
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.8 (591)

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

-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 minutes • Free Cancellation
4.8 (591)
from
$85
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for …More

Oahu, USA
4.8 (945)

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

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 minutes • Free Cancellation
4.8 (945)
from
$85
Kona Tradewind Catamaran Day Sail

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 …More

Big Island of Hawaii, USA
4.8 (50)

Kona Tradewind Catamaran Day Sail

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 minutes • Free Cancellation
4.8 (50)
from
$89
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own …More

Likely to Sell Out
Likely to Sell Out
Honolulu, USA
4.8 (349)

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own...

2 hours • Free Cancellation
4.8 (349)
from
$89
Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island …More

Oahu, USA
4.8 (1,740)

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

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 minutes • Free Cancellation
4.8 (1,740)
from
$90
Waikiki Sunset Cocktail Sail on the Moana Catamaran

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 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (2,366)

Waikiki Sunset Cocktail Sail on the Moana Catamaran

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 hours • Free Cancellation
4.9 (2,366)
from
$90
Waikiki Turtle Snorkeling & 6-in-1 Adventure 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), …More

Honolulu, USA
4.9 (446)

Waikiki Turtle Snorkeling & 6-in-1 Adventure 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 hours • Hotel pickup offered • Free Cancellation
4.9 (446)
from
$90

Frequently Asked Questions

These answers are based on answers previously given to Cool Hawaii customers' questions.

Recent activity reviews
Fun evening
New York City
Waikiki Sunset Cocktail Sail on the Moana Catamaran
kelikik0pa, Sep 2026
Fun evening
We had an amazing experience. We went out for two hours. The admission fee was priced well. The crew were so amazing. It was not crowded at all and the atmosphere was chill and fun. Best for groups, family friends adults.
Read more
Fabulous time!
New York City
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup
donnabY1972HD, Sep 2026
Fabulous time!
Great time. Lots of turtles! The crew was great and Dustin was the best!
Read more
Snorkeling
New York City
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup
deannw861, Sep 2026
Snorkeling
Great excursion with exceptional guides especially Dustin and Noah and Rowan.
Read more
Amazing as always! We do...
New York City
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
Jason_G, Sep 2026
Amazing as always! We do...
Amazing as always! We do this sailing every time we are in Honolulu and it’s always great. Good drinks, gorgeous views, and an awesome crew. Highly recommend!
Read more
Romantic sunset cruise.
New York City
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
705jeffu, Sep 2026
Romantic sunset cruise.
This was a great experience. We attended on a Friday which is 21 and over. The provided punch was very good. The sunset was gorgeous and everyone seemed to have a great time.
Read more
Good time
New York City
Waikiki Sunset Cocktail Sail on the Moana Catamaran
Passenger518461, Sep 2026
Good time
Bella and her crew were fantastic! We really enjoyed the experience. I would recommend.
Read more
Turtles and sailing
New York City
Waikiki Turtle Snorkel and Sail on Hawea Catamaran
jengay2018, Sep 2026
Turtles and sailing
The crew (Carlos, Des, Julia and Tommy) were amazing and made it a wonderful experience. We saw several turtles and had a great time
Read more
So kind and accommodating...
New York City
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
Minerva_L, Sep 2026
So kind and accommodating...
So kind and accommodating i would highly recommend!!! We got to see turtles, dolphins and different fishes.
Read more
Snorkeling with the turtles
New York City
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
O5530DDrussellm, Sep 2026
Snorkeling with the turtles
Great crew and guides. We saw three turtles while out as well as dolphins and variety of fish.
Read more
5 Stars Isn’t Enough. 😊
New York City
Waikiki Turtle Snorkel and Sail on Hawea Catamaran
Terrence_B, Sep 2026
5 Stars Isn’t Enough. 😊
Let me start with this: I HAD AN ABSOLUTE BLAST with Dez, Julia, Tommy, and Captain Carlos!!! This was my FIRST TIME snorkeling AND being out in open water, so I was equal parts excited, nervous, and ready to mind my business on the boat. But this crew made me feel so comfortable, safe, and excited to get in that water! And BABYYYY... once I got in?! I was a whole ass underwater Natty-Geo correspondent. I saw a needlefish, a little "chub" fish, AND a fish that looked just like DORY!!! I was swimming around like, "OH MY GOD, LOOK AT THAT!" every five seconds. LOL. Dez, Julia, Tommy, and Captain Carlos were honestly the dream team. Fun, welcoming, patient, gorgeous and just genuinely good vibes from beginning to end. They made my first snorkeling experience feel like a little Waikiki adventure I'll be talking about for a LONG time. And before anybody comes for my pictures... I PROMISE I HAVE BETTER PHOTOS!!! They're just living their best life on the GoPro right now. Hehe. Captain Carlos, Dez, Julia, and Tommy -- THANK YOU for making my first snorkeling experience so memorable. I hope I get lucky enough to have another adventure with y'all before | leave the island!
Read more
Great snorkeling.
New York City
Waikiki 2 hour Turtle Canyon Snorkeling Adventure
68teresitah, Sep 2026
Great snorkeling.
Disappointed that first was cancelled then when rescheduled again on our last day. Otherwise , it was awesome and will do it again hopefully on next visit if possible.
Read more
Amazing company
New York City
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
Meander19015932008, Sep 2026
Amazing company
That was such a breath taking experience. The crew was so kind & good company!
Read more
Perfect evening activity
New York City
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
172addisont, Sep 2026
Perfect evening activity
Very friendly staff and the perfect ride time to enjoy the water and sunset!
Read more
Great day out
New York City
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Anna_B, Sep 2026
Great day out
Kurt = ⭐️⭐️⭐️⭐️⭐️ Great way to see the island when visiting just for a few days. Loved all the scenic location stops, especially sunrise. Photography tips were great too!
Read more
Last minute booking!
New York City
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
AB19110, Sep 2026
Last minute booking!
Fun trip with the all girl Tuesday crew! Booked last minute and had a great time, beautiful sunset and saw dolphins 😍
Read more
Awesome Friday Nt Firework Experience
New York City
Friday Night Firework Cruise in Waikiki
jocelynd939, Sep 2026
Awesome Friday Nt Firework Experience
Awesome Firework Cruise experience! We are locals that bought our family to enjoy a Friday Nt in Waikiki. The crew was really fun and had very nice conversations with them! Would totally go again and recommend the Moana! Mahalo!
Read more
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