What are the best options for Hawaii Sailing Trips?

According to verified reviews on Cool Hawaii and TripAdvisor, the best Hawaii Sailing Trips are: Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui Waikoloa Catamaran Snorkel Sail Including Lunch Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

What are the best kid-friendly options for Hawaii Sailing Trips Activities?

According to verified reviews on Cool Hawaii and TripAdvisor, the best kid-friendly Hawaii Sailing Trips are: Waikiki Sunset Cocktail Sail on the Moana Catamaran Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady Waikiki 2 hour Turtle Canyon Snorkeling Adventure Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB View all kid-friendly Activities →

Which Hawaii Sailing Trips have Instant Confirmation?

Hawaii Sailing Trips with Instant Confirmation include: Waikiki Sunset Cocktail Sail on the Moana Catamaran Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Waikiki Turtle Snorkel and Sail on Hawea Catamaran Waikiki 2 hour Turtle Canyon Snorkeling Adventure Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB View all Activities with Instant Confirmation →

Which Hawaii Sailing Trips have Free Cancellation?

Hawaii Sailing Trips with Free Cancellation (in most cases up to 24 hours in advance of your activity date, check the specific activity page) include: Waikiki Sunset Cocktail Sail on the Moana Catamaran Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Waikiki Turtle Snorkel and Sail on Hawea Catamaran Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady Waikiki 2 hour Turtle Canyon Snorkeling Adventure View all Activities with Free Cancellation →

I need a ride! Which Hawaii Sailing Trips have Hotel Pickup?

No problem. These Hawaii Sailing Trips include Hotel Pickup: Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup Waikiki Turtle Snorkeling Adventure(8am) Half Day Oahu Combo Adventure: Bike, Sail and Snorkel Private Cruise Swim with Dolphin View all Activities with Hotel Pickup →

Got any more Hawaii trip ideas?

We sure do. Check out our curated lists of hand-picked Hawaii Activities. Top 10 Hawaii 2026 Senior-friendly tours Hawaii The best tours and activities for culture lovers in Hawaii Top Day Trips from Hawaii Things to do in Hawaii this summer View all Hawaii Trip Ideas →

What are the most popular styles of Tours and Activities in Hawaii?

Based on our sales data over the past year, the most popular styles of tours and activities in Hawaii are: Hawaii Luxury & Special Occasions Hawaii Luxury Tours Hawaii Outdoor Activities Hawaii Cruises, Sailing & Water Tours Hawaii Tours & Sightseeing View all tour styles in Hawaii →

THE TOP 10 Hawaii Sailing Trips (w/Prices)

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa …More

Kauai, USA

4.8 (563)

Nāpali Sunset Dinner Sail

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa...

4 to 5 hours Free Cancellation

4.8 (563)

from
$264

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

Kauai, USA

4.9 (558)

The Nāpali Coast Snorkel Excursion

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

Kona Morning Snorkel to Captain Cook Monument

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along …More

Big Island of Hawaii, USA

4.9 (480)

Kona Morning Snorkel to Captain Cook Monument

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along...

4 hours 30 minutes Free Cancellation

4.9 (480)

from
$179

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

Big Island of Hawaii, USA

4.8 (419)

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 (419)

from
$159

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

Big Island of Hawaii, USA

4.8 (382)

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 (382)

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

Honolulu, USA

4.9 (363)

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

4.9 (363)

from
$84

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

Oahu, USA

4.9 (322)

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 (322)

from
$73

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

Oahu, USA

5.0 (278)

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 (278)

from
$51

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 (264)

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 (264)

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 (256)

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 (256)

from
$45

Kona Afternoon Snorkel to Captain Cook Monument

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Spinner …More

Big Island of Hawaii, USA

4.9 (253)

Kona Afternoon Snorkel to Captain Cook Monument

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Spinner...

3 hours Free Cancellation

4.9 (253)

from
$136

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

Maui, USA

5.0 (225)

Lahaina Maui Sunset Sail on 'Alihilani

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 (225)

from
$127

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

Honolulu, USA

4.9 (223)

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 (223)

from
$67

Maui Molokini Snorkeling 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)

Maui Molokini Snorkeling 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
$221

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 (217)

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 (217)

from
$62

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

Maui, USA

4.8 (213)

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 (213)

from
$138

Hawaii Sailing Trips

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Nāpali Sunset Dinner Sail

The Nāpali Coast Snorkel Excursion

Kona Morning Snorkel to Captain Cook Monument

Waikoloa Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

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

Waikiki Sunset Boat Cruise

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

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

Kona Afternoon Snorkel to Captain Cook Monument

Lahaina Maui Sunset Sail on 'Alihilani

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Maui Sunset Sail

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