Hawaii Sailing Trips

103 Results
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 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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

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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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

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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

(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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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

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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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

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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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
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 …More

Likely to Sell Out
Likely to Sell Out
Kauai, USA

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

Likely to Sell Out
Likely to Sell Out
Maui, USA

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
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, …More

Big Island of Hawaii, USA

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
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical …More

Maui, USA

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical...

5 hours Free Cancellation
5.0 (135)
from
$269
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 …More

Likely to Sell Out
Likely to Sell Out
Kauai, USA

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
Polynesian Canoe Sunset Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (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 (128)
from
$250
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

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 (37)
from
$250
Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step …More

Maui, USA

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes Free Cancellation
4.8 (63)
from
$249

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