Hawaii Sailing Trips

102 Results
Sort by:
Featured
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

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 private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (17)

Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples...

2 hours • Free Cancellation
5.0 (17)
from
$300
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
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, …More

Oahu, USA
4.8 (62)

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night,...

1 hour • Free Cancellation
4.8 (62)
from
$90
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
South Shore Open Sail from Kewalo Harbor Including Drinks

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have …More

Oahu, USA
4.8 (26)

South Shore Open Sail from Kewalo Harbor Including Drinks

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have...

1 hour 30 minutes • Free Cancellation
4.8 (26)
from
$48
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
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
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
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
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
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from …More

Oahu, USA
4.9 (18)

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from...

2 hours • Free Cancellation
4.9 (18)
from
$70
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
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
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
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

Frequently Asked Questions

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

Recent activity reviews
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
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
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
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
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
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
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
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 night out
New York City
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
Hydes2014, Sep 2026
Great night out
Ava and the guys were great. Always walking around making sure we were having a good time and made sure we had a fresh drink.
Read more
Fun thing to do on a Friday night on Waikiki Beach
New York City
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
Howardru, Sep 2026
Fun thing to do on a Friday night on Waikiki Beach
Fun 90 minutes on a catamaran ride away from the beach to watch the fireworks go off. The crew was fun and entertaining. The drinks were not bad either. A nice election a beer wines and Hawaiian drinks fireworks lasted only five minutes but a fun thing to do to see from the actual ocean. My wife was happy that she got to wear her specialized sweatshirt just for the occasion 😊
Read more
Great time on the high sea
New York City
South Shore Open Sail from Kewalo Harbor Including Drinks
Johnathan_W, Aug 2026
Great time on the high sea
It was fun and the crew is great, the boat is beautiful. The captain dropped the sails and we took off like a rocket.
Read more
Amazing
New York City
Afternoon Sail & Snorkel to the Captain Cook Monument
Makayla_T, Aug 2026
Amazing
Super fun and a beautiful place to snorkel! Everyone was super friendly and inviting. Had a fun and relaxing boat ride.
Read more
Great experience! Highly recommend
New York City
Afternoon Sail & Snorkel to the Captain Cook Monument
Wendy_S, Aug 2026
Great experience! Highly recommend
Great Experience!! Boat was clean, lots of shade if you wanted it and lots of deck space if you didn’t. Crew was amazing and knowledgable! Saw dolphins on the way to and from the bay and lots of beautiful fish while snorkeling. Complimentary snacks, soda, water and juice were plentiful! Cocktails for purchase after snorkeling were super yummy! Would definitely recommend!
Read more
Great experience with awesome crew!
New York City
Waikiki Sunset Cocktail Cruise – Hilton Hawaiian Village
U8414MSdebbiem, Jul 2026
Great experience with awesome crew!
Started off with moving to a different pier due to weather and safety concerns, but they did shuttle us to new location. The Spirit of Aloha was a great boat with awesome crew! Loved the bento box, open bar and the entire experience which included gorgeous rainbows and sunset! Karin, Jackson and Brad were great!!
Read more
Hawaii Activities
Attractions
Guides
Calendar
View more
View more