Hawaii Sailing Trips

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Hawaii Activities

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Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (61)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes • Free Cancellation
4.8 (61)
from
$289
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
Private Oahu Sunset Charter with Tasting and Drinks

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people …More

Oahu, USA
5.0 (55)

Private Oahu Sunset Charter with Tasting and Drinks

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people...

120 to 150 minutes • Free Cancellation
5.0 (55)
from
$1,414
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
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
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and a beautiful Hawaiian sunset in one unforgettable trip. Start …More

Honolulu, USA
5.0 (49)

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and a beautiful Hawaiian sunset in one unforgettable trip. Start...

4 hours • Hotel pickup offered • Free Cancellation
5.0 (49)
from
$119
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
Akialoa Mā’alaea Sunset Sail

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (36)

Akialoa Mā’alaea Sunset Sail

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque...

2 hours • Free Cancellation
5.0 (36)
from
$108
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
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, …More

Oahu, USA
4.8 (35)

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May,...

2 hours • Free Cancellation
4.8 (35)
from
$250
Paragon Lahaina Sunset Sail

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (34)

Paragon Lahaina Sunset Sail

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the...

2 hours • Free Cancellation
5.0 (34)
from
$102
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
Waikiki Heritage and Diamond Head Wildlife Sail

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This experience emphasizes relaxation, scenic views of Oʻahu’s south shore, …More

Oahu, USA
4.8 (31)

Waikiki Heritage and Diamond Head Wildlife Sail

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This experience emphasizes relaxation, scenic views of Oʻahu’s south shore,...

1 hour 30 minutes • Free Cancellation
4.8 (31)
from
$119
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
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

Frequently Asked Questions

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

Recent activity reviews
Great time
New York City
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise
sarahkL4509NU, Sep 2026
Great time
Great time and good way to do multiple activities at one time! Nice boat and very experienced Captain Nate navigated us to turtle canyon. Scuba Clint guided us around the reefs and current to see all sorts of marine life. The toys they had were a lot of fun to play in the ocean. The snacks the crew had were awesome! The owner of the boat was very nice and experienced!
Read more
Awesome evening
New York City
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise
679jjd, Sep 2026
Awesome evening
Captain Nate and Scuba Clint were the best! We saw turtles, sting rays , reef white tip shark and so much more. Clint helped me learn how to paddle board. I was not graceful. The sunset was awesome. Captain Clint had a great selection of music for all age groups. I would book again and pass along to my friends.
Read more
Wonderful evening!
New York City
Paragon Lahaina Sunset Sail
Sharon_M, Sep 2026
Wonderful evening!
This was such a great sunset sail! The entire experience was perfect. The staff was very attentive throughout the entire evening. This was our favorite activity we did while in Maui!
Read more
Amazing
New York City
Private Oahu Sunset Charter with Tasting and Drinks
Guide28106223149, Sep 2026
Amazing
I can’t thank Mana Cruises enough for their amazing hospitality! Ella graciously greeted us. Captain Travis and Leah made each guest feel welcomed and safe! This is not my first time with them and certainly not the last! Mahalo Mana Cruises for making our Sunset cruise so special!!!
Read more
Sunset cruise Maui
New York City
Akialoa Mā’alaea Sunset Sail
Carol_S, Sep 2026
Sunset cruise Maui
We really enjoyed our sunset cruise. The staff was very attentive and entertaining! If we’d time, we would’ve done this excursion a second time! Thank you to Brandon, Matt and Megan!
Read more
Honeymoon cruise
New York City
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
camirenR, Sep 2026
Honeymoon cruise
Exceeded our expectations the food and drinks were amazing. Brandon and the rest of the crew aboard were excellent and got anything you needed right away. A little spendy but 100% worth the experience!!!
Read more
Perfect sail, incredible crew
New York City
Paragon Lahaina Sunset Sail
O2646KJellies, Sep 2026
Perfect sail, incredible crew
Really great experience for the price! We had such a perfect evening and the crew was incredible. would highly recommended
Read more
Turtle snorkeling
New York City
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
martinnN4650NC, Sep 2026
Turtle snorkeling
Wonderful experience we saw a bunch of turtle.
Read more
No Worries
New York City
Akialoa Mā’alaea Sunset Sail
Todd_J, Sep 2026
No Worries
Great experience, a real friendly crew, light hearted atmosphere and really great music. Highly recommend outing.👍👍
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
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
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
Exceptional experience.
New York City
Private Oahu Sunset Charter with Tasting and Drinks
V2985KBvictora, Aug 2026
Exceptional experience.
We booked a private tour with Mana Cruises, and it was truly an unforgettable experience! My son proposed during the cruise, and the crew went above and beyond with their incredible hospitality to make the moment extra special. Watching the sunset right after was pure magic. We couldn't have asked for a better evening or a more attentive crew!"The sunset was breathtaking, and the memories will last a lifetime. Highly recommend!"
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
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