Hawaii Sailing Trips

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Hawaii Activities

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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
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
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
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
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
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
Waikoloa Catamaran Snorkel Sail Including Lunch

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy …More

Big Island of Hawaii, USA
4.8 (108)

Waikoloa Catamaran Snorkel Sail Including Lunch

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy...

3 hours • Free Cancellation
4.8 (108)
from
$189
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
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above …More

Honolulu, USA
4.7 (67)

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above...

5 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.7 (67)
from
$197
Turtles & Tacos Luxury Catamaran Snorkel

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and …More

Maui, USA
4.8 (158)

Turtles & Tacos Luxury Catamaran Snorkel

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and...

3 hours • Free Cancellation
4.8 (158)
from
$199
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
Polynesian Canoe Day Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Oahu, USA
5.0 (28)

Polynesian Canoe Day Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours • Free Cancellation
5.0 (28)
from
$200
Polynesian Canoe Morning Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Oahu, USA
5.0 (18)

Polynesian Canoe Morning Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours • Free Cancellation
5.0 (18)
from
$200
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
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

Frequently Asked Questions

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

Recent activity reviews
Fun excursion!
New York City
Turtles & Tacos Luxury Catamaran Snorkel
Stephanie_Z, Sep 2026
Fun excursion!
Great experience. We did not see any turtles, so it's definitely not a guarantee as stated in the description but that's mother nature. The staff was awesome, the boat was clean and fun, lunch was delicious. Snorkeling was fun, even without turtles! Definitely recommended.
Read more
Best excursion in Hawaii
New York City
Turtles & Tacos Luxury Catamaran Snorkel
Gregory_h, Sep 2026
Best excursion in Hawaii
This was by far my favorite excursion that we did while we were in Hawaii. Very professional and wonderful crew. We had a blast.
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
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
Sail and snorkel fun
New York City
Waikoloa Catamaran Snorkel Sail Including Lunch
Billyfo079, Sep 2026
Sail and snorkel fun
Great experience and great crew. Enjoyed all aspects of the tour.
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
Great experience!
New York City
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Jeanine_D, Sep 2026
Great experience!
Crew was fantastic! Friendly and experienced helping guests that need support! Recommend this company!
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
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
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
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
Snorkeling Maui 2026
New York City
Snorkel Sail Adventure off Ka’anapali Beach in Maui
Go251646, Aug 2026
Snorkeling Maui 2026
Great experience overall! The boat was clean, and the staff was extremely friendly, knowledgeable, and accommodating. Since the trip wasn’t overly booked, everyone had plenty of space to sit down, relax, and enjoy the experience.The only two things I would mention are the last-minute change to the pickup/drop-off location, which resulted in a 20–30 minute walk, and the food options. Everything looked delicious, but it would be nice to have a few options for guests who don’t eat meat or meat products.Overall, we really enjoyed the trip and appreciated how welcoming and accommodating the staff was!
Read more
Snorkeling + island...
New York City
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
Kiersten_M, Aug 2026
Snorkeling + island...
Snorkeling + island history + fabulous and energetic staff who are dedicated and clearly love their jobs
Read more
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