Hawaii Sailing Trips

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Hawaii Activities

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Honolua Snorkel Sail from Lahaina

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way, …More

Maui, USA
5.0 (58)

Honolua Snorkel Sail from Lahaina

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way,...

5 hours • Free Cancellation
5.0 (58)
from
$181
Hawaiian Canoe Sailing Experience in Maui

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (59)

Hawaiian Canoe Sailing Experience in Maui

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning...

2 hours • Free Cancellation
4.9 (59)
from
$179
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
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
Sound of the Ocean Whale Watch Sail

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them …More

Maui, USA
5.0 (1)

Sound of the Ocean Whale Watch Sail

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them...

2 hours • Free Cancellation
5.0 (1)
from
$164
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
Waikoloa Signature Catamaran Sunset Sail

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
4.8 (413)

Waikoloa Signature Catamaran Sunset Sail

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers...

90 to 120 minutes • Free Cancellation
4.8 (413)
from
$159
Day's End Cocktail Sunset Sail

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (96)

Day's End Cocktail Sunset Sail

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted...

2 hours • Free Cancellation
4.9 (96)
from
$159
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
Moana’s Luxury semi-private Sunset Cruise on Nalu

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback …More

Oahu, USA
5.0 (20)

Moana’s Luxury semi-private Sunset Cruise on Nalu

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback...

2 hours • Free Cancellation
5.0 (20)
from
$150
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.6 (81)

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience...

2 hours • Free Cancellation
4.6 (81)
from
$142
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
BYOB Friday Night Fireworks Cruise

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights …More

Oahu, USA
5.0 (5)

BYOB Friday Night Fireworks Cruise

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights...

2 hours 30 minutes • Free Cancellation
5.0 (5)
from
$139
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
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
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 …More

Big Island of Hawaii, USA
4.9 (252)

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...

3 hours • Free Cancellation
4.9 (252)
from
$136

Frequently Asked Questions

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

Recent activity reviews
So worth the cost , crew...
New York City
Day’s End Cocktail Sunset Sail
Brenda_R, Sep 2026
So worth the cost , crew...
So worth the cost , crew were friendly, helpful very attentive to everyone & Captain Jordan knew her stuff! Captain kept us in the best water since the wind was very strong, I felt very comfortable the whole ride. Highly recommend!
Read more
Greatest time sunset cruise
New York City
Moana’s Luxury semi-private Sunset Cruise on Nalu
334duaneg, Sep 2026
Greatest time sunset cruise
One of the most beautiful times on a dream vacation in Hawaii Sunset, cruise and beautiful scenery with friends family great drinks had a fantastic time . ps I would love to do it again. I recommend it.
Read more
Staff was great! Not only...
New York City
Ka’anapali Luxury Sunset Cocktail Sail with Open Bar in Maui
Shane_F, Sep 2026
Staff was great! Not only...
Staff was great! Not only did they make sure we had everything we needed they socialized with everyone. Would highly recommend other to go.
Read more
A’hui hou
New York City
Waikoloa Signature Catamaran Sunset Sail
Karen_M, Sep 2026
A’hui hou
Fantastic!!! Crew and captain were attentive and personable.. drinks were plenty and food perfect.. I would do this again and again ! This time we were celebrating our 32nd wedding anniversary and it was perfect .. go here if you can ❤️🌋❤️🤙🤙
Read more
Amazing
New York City
Moana’s Luxury semi-private Sunset Cruise on Nalu
U5007FTkylem, Sep 2026
Amazing
This was a great experience. They had very good service and amazing staff.
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
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
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
Highly recommend booking...
New York City
Day’s End Cocktail Sunset Sail
Alessandra_L, Sep 2026
Highly recommend booking...
Highly recommend booking - staff was kind and knowledgeable and the ocean views were truly amazing!!
Read more
Fantastic sunset adventure
New York City
Waikoloa Signature Catamaran Sunset Sail
suelW5985QI, Sep 2026
Fantastic sunset adventure
Our catamaran cruise was beautiful and such a smooth ride. Crew was great and it even included a delicious dinner that was a surprise. We just expected snacks. Variety of cocktails were offered to meet everyone's tastes.
Read more
Great crew!
New York City
Deluxe Sail & Snorkel to the Captain Cook Monument
O2007RPnoelc, Sep 2026
Great crew!
My wife and I had a great time. Even though we had some trouble due to the hurricane approaching, the captain & crew did all the could to make the experience fun and get us in the water.
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
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
Beautiful 1st wedding anniversary celebration
New York City
Ka’anapali Luxury Sunset Cocktail Sail with Open Bar in Maui
Eleanor_M, Aug 2026
Beautiful 1st wedding anniversary celebration
We were trying to find a perfect way to celebrate our 1st wedding anniversary and this went above and beyond
Read more
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