Hawaii Sailing Trips

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Hawaii Activities

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Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (211)

Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing...

2 hours • Free Cancellation
4.8 (211)
from
$138
Midday Whale Watch: Mā’alaea Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (103)

Midday Whale Watch: Mā’alaea Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours • Free Cancellation
4.9 (103)
from
$100
2-Hour Oahu Sunset Catamaran Sail

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. …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (138)

2-Hour Oahu Sunset Catamaran Sail

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 hours • Free Cancellation
4.9 (138)
from
$130
Small Group Waikiki Sunset Sailing Tour

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 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (118)

Small Group Waikiki Sunset Sailing Tour

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 hours • Free Cancellation
4.9 (118)
from
$99
Waikiki small group turtle snorkeling & sailing

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 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (105)

Waikiki small group turtle snorkeling & sailing

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 hours • Free Cancellation
5.0 (105)
from
$99
Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, …More

Maui, USA
4.9 (218)

Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve,...

5 hours • Free Cancellation
4.9 (218)
from
$200
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

Oahu, USA
4.9 (261)

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 hours • Free Cancellation
4.9 (261)
from
$50
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, …More

Maui, USA
5.0 (130)

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers,...

5 hours • Free Cancellation
5.0 (130)
from
$163
Snorkel Sail Adventure off Ka'anapali Beach in Maui

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, …More

Likely to Sell Out
Likely to Sell Out
Lahaina, USA
5.0 (49)

Snorkel Sail Adventure off Ka'anapali Beach in Maui

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky,...

4 hours • Free Cancellation
5.0 (49)
from
$193
Maui Turtle Snorkel & Sail with Lunch & Open Bar

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (41)

Maui Turtle Snorkel & Sail with Lunch & Open Bar

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear...

2 hours 30 minutes • Free Cancellation
4.8 (41)
from
$122
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 Cook Monument" …More

Big Island of Hawaii, USA
4.9 (479)

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 Cook Monument"...

4 hours 30 minutes • Free Cancellation
4.9 (479)
from
$179
Private Catamaran Charter in Waikiki (1-6 Guests)

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 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (25)

Private Catamaran Charter in Waikiki (1-6 Guests)

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 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 …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
Morning Whale Watch: Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (29)

Morning Whale Watch: Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours • Free Cancellation
4.9 (29)
from
$100
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (33)

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and...

5 hours • Free Cancellation
5.0 (33)
from
$203
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (19)

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea,...

2 hours • Free Cancellation
4.8 (19)
from
$279

Frequently Asked Questions

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

Recent activity reviews
Great sunset cruise from Ko'Olina
New York City
2-Hour Oahu Sunset Catamaran Sail
craigandt, Sep 2026
Great sunset cruise from Ko'Olina
Fantastic crew and evening trip. Location is great for MVCI guests and owners and a short walk away. The staff was friendly, the weather was great and we had a fantastic time.For guests at MVCI - this is a must do for your trip!
Read more
Amazing sunset cruise
New York City
2-Hour Oahu Sunset Catamaran Sail
450halc, Sep 2026
Amazing sunset cruise
We had an amazing time on the sunset sail. What a great way to watch a beautiful Hawaiian sunset. Elijah, Jake, and Miriam were an excellent crew. They were attentive and made the tour a great one. We would highly recommend this tour
Read more
An Amazing Experience with Sail Maui!
New York City
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
hongc884, Sep 2026
An Amazing Experience with Sail Maui!
⭐⭐⭐⭐⭐ An Amazing Experience with Sail Maui!I had such an incredible experience with Sail Maui on September 15th on the snorkeling trip to Lanai. Honestly, this was one of the highlights of my Hawaii trip, and it was worth every penny!The crew was absolutely amazing. They were friendly, welcoming, attentive, and genuinely caring. I became a little seasick during the trip but didn’t tell anyone. I thought I would just lie down on the nets and wait for it to pass. Somehow, the crew noticed that I wasn’t feeling well and immediately came to check on me.They offered me a ginger chew, an ice bag to hold, and medicine. The ginger chew and ice bag worked wonderfully! They continued checking on me frequently and kept offering me drinks to make sure I was comfortable. I was so impressed by how observant and thoughtful they were. They didn’t just provide good service—they truly cared about how I was feeling.And the snorkeling was spectacular! The water was beautiful and incredibly clear. We saw so many colorful fish, sea turtles, and beautiful coral reefs. It was an amazing experience to see all of that underwater.Then came another unforgettable moment: the captain stopped the boat so we could watch dolphins playing right in front of us! Seeing them so close, swimming and playing in the ocean, was absolutely magical. 🐬From beginning to end, everything was wonderful—the beautiful ocean, incredible snorkeling, amazing wildlife, and especially the fantastic crew.Hawaii hospitality is truly unmatched, and the Sail Maui crew is a perfect example of it. ❤️Thank you, Sail Maui, for giving me such a memorable experience. I would absolutely do this trip again and highly recommend it to anyone visiting Maui! 🌺🐢🐬
Read more
Best snorkeling experience we've had
New York City
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
seanpF4297KZ, Sep 2026
Best snorkeling experience we've had
Every part of the crew was absolutely amazing. We had an amazing experience and highly recommend. The crew was not only very sweet and caring, they were very attentive to everyone and their needs. We were fortunate to be able to see a monk seal and whale shark in a matter of 30 minutes which we heard was extremely rare. 10/10 would definitely come back
Read more
Loved it!
New York City
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
tonih616, Sep 2026
Loved it!
They were wonderful! Everyone was friendly and knowledgable, and we had a lot of fun. We will definitely book again!
Read more
Great snorkeling on Maui!
New York City
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
Marisa_F, Sep 2026
Great snorkeling on Maui!
Wonderful snorkeling trip with a great crew. Lunch was delicious. We saw a lot of turtles. The boat is beautifully maintained.
Read more
Amazing service
New York City
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
Tatiana_J, Sep 2026
Amazing service
Captain Patrick and his crew were amazing, friendly, knowledgeable and helpful. Weather was perfect, drinks cold , ocean water was great.
Read more
Sunset boat ride
New York City
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
robertbE1580JV, Sep 2026
Sunset boat ride
Excellent experience worth the price. Captain Spence and Logan took care of us. A highlight of our trip. A relaxing boat ride with a fun ride back to the pier. 10 out of 10!!
Read more
Maui Sunset Sail from Lahaina
New York City
Maui Sunset Sail
F6516QAlarryf, Sep 2026
Maui Sunset Sail from Lahaina
Friendly crew. Sunset and rainbows were awesome. We've been on PacWhale sailings before and will go again. The cause is wonderful and the price is fair. We saw a wonderful sunset and multiple rainbows above Maui.
Read more
Great time!!!
New York City
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
Q7130NUnicolec, Sep 2026
Great time!!!
So fun!!!!! Great crew. Great energy.
Read more
Funnest snorkel trip ever
New York City
Deluxe Sail & Snorkel to the Captain Cook Monument
tudmasterg, Sep 2026
Funnest snorkel trip ever
What an amazing fun day. The crew were friendly and took us to 2 awesome snorkeling spots. They also shared the history and facts about where we were. Captain Ed, Joshua and please forgive me, I can’t remember the woman’s name. A local and it started with K. She was so nice and helpful. I recommend 100%
Read more
Really nice day on the Sea Paradise Catamaran
New York City
Deluxe Sail & Snorkel to the Captain Cook Monument
GWBridgeNewYork, Sep 2026
Really nice day on the Sea Paradise Catamaran
An absolutely awesome snorkel/catamaran trip. The crew was amazing (Captain Jon and Crew Beau, Taylor, Austin, and I unfortunately forgot the name of the fourth one, a pleasant young lady). Along the way and back they take turns giving you the Hawaiian history of the sacred locations along the shore and what occurred there hundreds of years ago amongst the native Hawaiians and with Captain Cook. The two snorkel spots were teeming with fish. The crew were steady (but not overwhelming) in offering snacks and drinks, and turning on the showers for you after coming in from snorkeling. Captain Jon was either good (or lucky, LOL) in finding pods of spinner dolphins for us to watch. Lunch during the ride back was also pleasant. A nice sandwich bar. The staff assisted me in making a Hawaiian tuna wrap!
Read more
Great time
New York City
Maui Turtle Snorkel & Sail with Lunch & Open Bar
lindsaycU7675QC, Aug 2026
Great time
Excellent experience! The crew was great
Read more
Sail & Snorkel aboard The Gemini
New York City
Snorkel Sail Adventure off Ka’anapali Beach in Maui
534AnneS534, Aug 2026
Sail & Snorkel aboard The Gemini
We had an awesome experience aboard the Gemini. We met the tour guide by the Westin, then walked together to the other side of Black Rock, where we boarded the catamaran from the beach. The surf was apparently too rough to board by the Westin that day. The boat seemed to have the right amount of people aboard, so it did not feel packed. You could easily move about the boat with plenty of room.It took us to the West Maui snorkel spot, Honolua Bay. The water was clear and fish were plentiful. We even saw a turtle! Lunch and drinks were served on the boat after snorkeling. The crew was great, and really helped ensure we all had fun. I would highly recommend the tour.
Read more
Awesome!
New York City
Waikiki small group turtle snorkeling & sailing
637kamall, Aug 2026
Awesome!
Awesome experience. We did a ride with him twice on our 10 day trip. He was very helpful and made it fun for the family. He also knows what he’s doing with a lot of experience so safety is not a concern either. He watched our youngest son which gave me a chance to snore as well. We will definitely be going with him next time we’re in Waikiki! PS. The drone footage is 100% worth every penny.
Read more
The best sunset cruise in Waikiki!
New York City
Small Group Waikiki Sunset Sailing Tour
Haley_G, Aug 2026
The best sunset cruise in Waikiki!
We had such a wonderful experience on our sunset cruise off the coast of Waikiki with Captain Tony! We booked through Cool Hawaii, and it was such a fun surprise to realize that Captain Tony had actually taken my friends and me out on a cruise back in 2023 as well, although we had booked through a different company at the time. Captain Tony was incredibly sweet, personable, and professional. He pointed out different sights along the coast, took photos of us, gave us great recommendations for things to do and places to visit, and was genuinely so kind and polite throughout the entire experience.The ride itself was peaceful and relaxing, and watching the sunset from the water was absolutely beautiful. We had such a great time and would definitely book with Captain Tony again. Highly recommend!
Read more
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