Hawaii Sailing Trips

102 Results
Sort by:
Price (High to Low)
Filter
Languages Clear
Time of Day Clear
47
52
46
Duration Clear
3
88
16
1
0
Price Clear
$0 $500+
Rating Clear
88
99
100
Specials Clear
102
47
0
12
2
Features Clear
4
79
85
4
87
2
Accessibility Clear
0
34
81
Families Clear
82
25
49

Hawaii Activities

Attractions

Guides

Calendar

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
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
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.5 (38)

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

1 hour 30 minutes • Free Cancellation
4.5 (38)
from
$120
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
Luxury Catamaran Whale Watch

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way …More

Maui, USA
4.9 (90)

Luxury Catamaran Whale Watch

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way...

2 hours • Free Cancellation
4.9 (90)
from
$119
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
'Alihilani Lahaina Sunset Sail

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (195)

'Alihilani Lahaina Sunset Sail

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for...

2 hours 30 minutes • Free Cancellation
5.0 (195)
from
$117
Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and …More

Maui, USA
4.8 (85)

Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and...

2 hours • Free Cancellation
4.8 (85)
from
$112
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise …More

Oahu, USA
4.5 (47)

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise...

2 hours 30 minutes • Free Cancellation
4.5 (47)
from
$110
Kona Signature Catamaran Sunset Sail

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
4.8 (349)

Kona Signature Catamaran Sunset Sail

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean...

1 hour 30 minutes • Free Cancellation
4.8 (349)
from
$109
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
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
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
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
Afternoon Sail With the Whales from 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
5.0 (1)

Afternoon Sail With the Whales from 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
5.0 (1)
from
$100
Midmorning Whale Watch from 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
4.5 (2)

Midmorning Whale Watch from 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
4.5 (2)
from
$100

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
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
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
Sunset fun
New York City
‘Alihilani Lahaina Sunset Sail
Ramiro_F, Sep 2026
Sunset fun
Great crew, Great cruise. Recommend highly. Made great friends and crew made sure everyone was taken care off.
Read more
Lovely Maui Experience
New York City
‘Alihilani Lahaina Sunset Sail
laurazD7578IN, Sep 2026
Lovely Maui Experience
Jess Jen and Brayden were wonderful hosts. The food and drinks were great. It was a relaxing and fun evening.
Read more
Excellent tour and experience
New York City
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
P8063NGpaula, Sep 2026
Excellent tour and experience
Excelllent communication. Our original tour date was cancelled and we were offered a full refund or we could rebook for another day. Glad we rebooked. The experience was perfect. The tour guides were friendly and professional.
Read more
Beautiful weather and sunset 🌅
New York City
Kona Signature Catamaran Sunset Sail
danieljS6776VI, Sep 2026
Beautiful weather and sunset 🌅
Had an AMAZING experience! We highly recommend this experience.
Read more
Sunset Sail was the best!
New York City
Kona Signature Catamaran Sunset Sail
Nancy_R, Sep 2026
Sunset Sail was the best!
Staff was helpful, polite and made the cruise fun. The bar drinks were great and the teriyaki chicken and rice were tasty
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
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
Such a pretty and...
New York City
Waikiki Sunset Cocktail Cruise – Hilton Hawaiian Village
Jason_W, Sep 2026
Such a pretty and...
Such a pretty and relaxing sunset cruise. The crew was friendly and the views were amazing! Definitely would recommend!
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
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
The Best!
New York City
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Cristina_S, Sep 2026
The Best!
Fantastic crew and captain (captain nick, crewmates nick, and mike?). They quite literally sprang into action when a passenger got injured in the water by a jelly fish. I have never felt more safe, secure, and well taken care of during this excursion. I’d would use this company with this crew anytime time I’m back again on the island. Great experience and fun!
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
Hawaii Activities
Attractions
Guides
Calendar
View more
View more