What are the best options for Hawaii Sailing Trips?

According to verified reviews on Cool Hawaii and TripAdvisor, the best Hawaii Sailing Trips are: Waikiki 2 hour Turtle Canyon Snorkeling Adventure Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure Waikiki Sunset Cocktail Sail on the Moana Catamaran Waikiki Sunset Cruise: 2-Hour Catamaran & Swim Adventure in Oahu Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

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: #1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson The Nāpali Coast Snorkel Excursion Afternoon Ali'i Adventure Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion Nāpali Sunset Dinner Sail View all kid-friendly Activities →

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

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

THE TOP 10 Hawaii Sailing Trips (w/Prices)

Q: Which Hawaii Sailing Trips have Instant Confirmation?

Hawaii Sailing Trips with Instant Confirmation include: Private Cruise Swim with Dolphin 3 Hour Luxury Private Sailing Catamaran for 7-12 People 3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People 2hr Luxury Private Sailing Catamaran for 7-12 People 2 Hour Private Catamaran Charter in Waikiki (7-12 Guests) View all Activities with Instant Confirmation →

Q: 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: 3 Hour Luxury Private Sailing Catamaran for 7-12 People 3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People Private Catamaran Charter for Exclusive Celebrations 2hr Luxury Private Sailing Catamaran for 7-12 People Private Oahu Sunset Charter with Tasting and Drinks View all Activities with Free Cancellation →

Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and anniversaries. An Impressive Swimming Experience with Wild …More

Oahu, USA

Private Cruise Swim with Dolphin

Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and anniversaries. An Impressive Swimming Experience with Wild...

3 hours Hotel pickup offered

from
$3,901

3 Hour Luxury Private Sailing Catamaran for 7-12 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Oahu, USA

5.0 (1)

3 Hour Luxury Private Sailing Catamaran for 7-12 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

3 hours Free Cancellation

5.0 (1)

from
$1,995

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Oahu, USA

5.0 (2)

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

3 hours Free Cancellation

5.0 (2)

from
$1,595

Private Catamaran Charter for Exclusive Celebrations

Enjoy the luxury of having your own 35-passenger catamaran for a private charter on the Pacific. Perfect for exclusive celebrations or a fun day with …More

Oahu, USA

5.0 (1)

Private Catamaran Charter for Exclusive Celebrations

Enjoy the luxury of having your own 35-passenger catamaran for a private charter on the Pacific. Perfect for exclusive celebrations or a fun day with...

2 hours Free Cancellation

5.0 (1)

from
$1,500

2hr Luxury Private Sailing Catamaran for 7-12 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Oahu, USA

5.0 (4)

2hr Luxury Private Sailing Catamaran for 7-12 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

2 hours Free Cancellation

5.0 (4)

from
$1,495

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

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 …More

Oahu, USA

5.0 (2)

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6...

2 hours Free Cancellation

5.0 (2)

from
$1,200

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Oahu, USA

4.8 (14)

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

2 hours Free Cancellation

4.8 (14)

from
$1,150

Private Morning Ceremony Sailing Charter

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to …More

Oahu, USA

Private Morning Ceremony Sailing Charter

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to...

1 hour 30 minutes Free Cancellation

from
$1,000

Private Catamaran Charter in Waikiki (1-6 Guests)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on …More

Oahu, USA

5.0 (25)

Private Catamaran Charter in Waikiki (1-6 Guests)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on...

2 hours Free Cancellation

5.0 (25)

from
$900

Private Catamaran Sunset Sail in Waikiki

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which …More

Oahu, USA

5.0 (11)

Private Catamaran Sunset Sail in Waikiki

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which...

2 hours Free Cancellation

5.0 (11)

from
$900

#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed …More

Oahu, USA

5.0 (4)

#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed...

2 hours Free Cancellation

5.0 (4)

from
$450

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

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

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

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, …More

Maui, USA

4.8 (19)

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea,...

2 hours Free Cancellation

4.8 (19)

from
$279

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, …More

Big Island of Hawaii, USA

5.0 (6)

Afternoon Ali'i Adventure

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests,...

3 hours Free Cancellation

5.0 (6)

from
$276

Hawaii Sailing Trips

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Private Cruise Swim with Dolphin

3 Hour Luxury Private Sailing Catamaran for 7-12 People

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

Private Catamaran Charter for Exclusive Celebrations

2hr Luxury Private Sailing Catamaran for 7-12 People

Private Oahu Sunset Charter with Tasting and Drinks

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

Private Morning Ceremony Sailing Charter

Private Catamaran Charter in Waikiki (1-6 Guests)

Private Catamaran Sunset Sail in Waikiki

#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

Waikiki private Day Tour and Sunset sail for couples

The Nāpali Coast Snorkel Excursion

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Afternoon Ali'i Adventure

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