Hawaii Sailing Trips

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Hawaii Activities

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Kauai’s Na Pali Coast Snorkel and Sail Tour

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making …More

Likely to Sell Out
Likely to Sell Out
Kauai, USA
4.9 (558)

Kauai’s Na Pali Coast Snorkel and Sail Tour

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making...

6 hours • Free Cancellation
4.9 (558)
from
$292
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
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), …More

Honolulu, USA
4.9 (446)

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP),...

3 hours • Hotel pickup offered • Free Cancellation
4.9 (446)
from
$90
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
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
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own …More

Likely to Sell Out
Likely to Sell Out
Honolulu, USA
4.8 (349)

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own...

2 hours • Free Cancellation
4.8 (349)
from
$89
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (316)

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the...

1 hour 30 minutes • Free Cancellation
4.9 (316)
from
$73
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far …More

Oahu, USA
4.9 (261)

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far...

2 hours • Free Cancellation
4.9 (261)
from
$50
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle, …More

Oahu, USA
4.9 (255)

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle,...

1 hour 30 minutes • Free Cancellation
4.9 (255)
from
$53
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
Waikiki Sunset Boat Cruise

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (240)

Waikiki Sunset Boat Cruise

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as...

1 hour 30 minutes • Free Cancellation
5.0 (240)
from
$50
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
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique …More

Likely to Sell Out
Likely to Sell Out
Honolulu, USA
4.9 (215)

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique...

2 hours • Free Cancellation
4.9 (215)
from
$71
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
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic …More

Oahu, USA
4.9 (210)

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic...

1 hour 30 minutes • Free Cancellation
4.9 (210)
from
$62
'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

Frequently Asked Questions

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

Recent activity reviews
Fabulous time!
New York City
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup
donnabY1972HD, Sep 2026
Fabulous time!
Great time. Lots of turtles! The crew was great and Dustin was the best!
Read more
Snorkeling
New York City
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup
deannw861, Sep 2026
Snorkeling
Great excursion with exceptional guides especially Dustin and Noah and Rowan.
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
The experience was...
New York City
Waikiki Sunset Boat Cruise
Jay_P, Sep 2026
The experience was...
The experience was relaxing and beautiful! We were provided with a complimentary drink and snack. Good hosts!
Read more
Relaxing cruise
New York City
Waikiki Sunset Boat Cruise
Michal_Z, Sep 2026
Relaxing cruise
It was calm almost like privatr cruise with good music and good ladies. We saw beautiful rainbow and sunset.
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
So kind and accommodating...
New York City
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
Minerva_L, Sep 2026
So kind and accommodating...
So kind and accommodating i would highly recommend!!! We got to see turtles, dolphins and different fishes.
Read more
Snorkeling with the turtles
New York City
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
O5530DDrussellm, Sep 2026
Snorkeling with the turtles
Great crew and guides. We saw three turtles while out as well as dolphins and variety of fish.
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
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 company
New York City
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
Meander19015932008, Sep 2026
Amazing company
That was such a breath taking experience. The crew was so kind & good company!
Read more
Perfect evening activity
New York City
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
172addisont, Sep 2026
Perfect evening activity
Very friendly staff and the perfect ride time to enjoy the water and sunset!
Read more
Great day out
New York City
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Anna_B, Sep 2026
Great day out
Kurt = ⭐️⭐️⭐️⭐️⭐️ Great way to see the island when visiting just for a few days. Loved all the scenic location stops, especially sunrise. Photography tips were great too!
Read more
Last minute booking!
New York City
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
AB19110, Sep 2026
Last minute booking!
Fun trip with the all girl Tuesday crew! Booked last minute and had a great time, beautiful sunset and saw dolphins 😍
Read more
Fantastic Evening On the Water
New York City
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Raewyn_B, Sep 2026
Fantastic Evening On the Water
We had a wonderful time out on the water! The music was great- plenty of drinks & the crew made sure we were all looked after🍹The sunset was amazing - a fabulous memory to take home from Honolulu🌅
Read more
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