Hawaii Sailing Trips

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Hawaii Activities

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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
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

Oahu, USA
4.9 (1,743)

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....

2 hours • Free Cancellation
4.9 (1,743)
from
$50
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
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

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 …More

Kauai, USA
4.8 (1,544)

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

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 hours • Free Cancellation
4.8 (1,544)
from
$223
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
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

Oahu, USA
4.9 (988)

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...

2 hours • Free Cancellation
4.9 (988)
from
$55
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
Sunset and Manta Ray Snorkel Adventure

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
4.9 (855)

Sunset and Manta Ray Snorkel Adventure

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of...

2 hours 15 minutes • Free Cancellation
4.9 (855)
from
$155
Four Winds Molokini Snorkeling Tour from Maalaea Harbor

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 …More

Maui, USA
4.8 (830)

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

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 hours • Free Cancellation
4.8 (830)
from
$213
Snorkel with Manta Rays Guaranteed

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 …More

Big Island of Hawaii, USA
4.8 (743)

Snorkel with Manta Rays Guaranteed

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 minutes • Free Cancellation
4.8 (743)
from
$141
Afternoon Sail & Snorkel to the Captain Cook Monument

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you …More

Big Island of Hawaii, USA
4.9 (734)

Afternoon Sail & Snorkel to the Captain Cook Monument

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you...

3 hours • Free Cancellation
4.9 (734)
from
$136
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

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 …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
5.0 (711)

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

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 hours • Free Cancellation
5.0 (711)
from
$189
Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

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

Oahu, USA
4.8 (595)

Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

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 (595)
from
$56
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
Deluxe Sail & Snorkel to the Captain Cook Monument

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain …More

Big Island of Hawaii, USA
4.9 (578)

Deluxe Sail & Snorkel to the Captain Cook Monument

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain...

4 hours 30 minutes • Free Cancellation
4.9 (578)
from
$179
Kauai: Leila Na Pali Sunset Dinner Sail

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 …More

Likely to Sell Out
Likely to Sell Out
Kauai, USA
4.8 (563)

Kauai: Leila Na Pali Sunset Dinner Sail

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 hours • Free Cancellation
4.8 (563)
from
$264

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
Amazing sail & sunset cruise!
New York City
Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure
Dama_M, Sep 2026
Amazing sail & sunset cruise!
Great sunset cruise! The crew was very helpful & friendly-Alex, Alejandro & Jandy❤️ I would definitely go again🌊😊
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
Experience that lives up to the hype + plused by the crew
New York City
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Jason_H, Sep 2026
Experience that lives up to the hype + plused by the crew
Great for families with small kids. Not overbooked, great boat and accommodations, multiple ways for young kids to engage in the experience - life vests, floating vessels, placards to pinpoint wildlife, etc. crew was very engaging, personable, and caters to our family needs. Even let the kids "drive" the boat. Couldn't recommend more.
Read more
Dream Sailing!
New York City
Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure
Colleen_E, Sep 2026
Dream Sailing!
Phenomenal experience. Capt Mo, John, & Kai were wonderful & entertaining. We felt so confident with their seamanship and safe with thier knowledge of the area and Swim precautions at the same time they made it a fun and humorous adventure. Little Dog stole the show though! Mahalo for a wonderful time!
Read more
Awesome trip
New York City
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
leeaY7148QU, Sep 2026
Awesome trip
Wonderful experienced crew and clean boat. Definitely a recommend for those who are new to snorkeling. 10/10 would use again the next time we’re here.
Read more
Lucy, Liza & Crash were...
New York City
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
Carlos_T, Sep 2026
Lucy, Liza & Crash were...
Lucy, Liza & Crash were amazing ! it was well worth it. they were friendly, funny and very knowledgable.
Read more
Great day snorkeling
New York City
Deluxe Sail & Snorkel to the Captain Cook Monument
ShellyM926, Sep 2026
Great day snorkeling
We had a wonderful time with two snorkeling stops. We felt that we had plenty of time to snorkel at each. We also enjoyed our snorkel break when the captain took us on a sailing trip and we found dolphins. The continental breakfast and lunch (sandwich) was also quality. The bathroom on the boat was very clean and modern.
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
Awesome Laid-back sunset cruise
New York City
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
Kim_U, Sep 2026
Awesome Laid-back sunset cruise
Wonderful relaxing experience at great price! Excellent crew! Very helpful and pleasant! Surprise charcuterie snackboard! Highly recommend if your laid back.
Read more
10/10 manta day experience
New York City
Snorkel with Manta Rays Guaranteed
hj260898, Sep 2026
10/10 manta day experience
We were visiting from England and researched the most ethical and value for money tour, sea paradise came to the top of our searches. We received plenty of information prior to arriving, parking was located along Kaleiopapa road. We were greeted by an enthusiastic crew who made everyone feel comfortable. The manta ray experience was incredible! We were very lucky and saw dolphins as well as tuna during our snorkelling time. On the way back to the pier we were provided with drinks and an amazing view of the milkway. I would do this tour all over again if I had time. I would recommend this tour to anyone visiting Kailua Kona , it is a must do.
Read more
Turtles Galore!
New York City
Waikiki 2 hour Turtle Canyon Snorkeling Adventure
Teresa_F, Sep 2026
Turtles Galore!
We had a wonderful time on this catamaran sail. Jamie our captain was very sociable and informative. We felt very safe and well cared for by all the crew. This was September and we were surrounded by turtles. Plus it was a beautiful ride with views of Ohau. Great experience.
Read more
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