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Top USA Sailing Trips

377 Results
6-Night Private Charter in Lake Clark National Park

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group …More

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group...

7 days
5.0 (1)
from
$30,769
3-Night Private Charter in Lake Clark National Park

Spend three nights and four days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group …More

Spend three nights and four days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group...

4 days
5.0 (1)
from
$20,513
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
Key West Private Wind & Wine Charter

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Shore Excursions three years running. See the sunset …More

Key West, USA

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Shore Excursions three years running. See the sunset...

2 hours (approx.) Free Cancellation
5.0 (1,716)
from
$3,499
Private Luxurious Sailing Cruise in San Diego Bay

This is the best most luxurious sailing tour in Southern California. Limited to you and 5 guests, and based on your most specific preferences, we'll …More

La Jolla, USA

This is the best most luxurious sailing tour in Southern California. Limited to you and 5 guests, and based on your most specific preferences, we'll...

2 hours Free Cancellation
5.0 (13)
from
$2,700
Private Key West Morning Sail, Snorkel & Kayak Excursion

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge. …More

Special Offer
Special Offer
Key West, USA

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4 hours 30 minutes (approx.) Free Cancellation
$2,399
$2,270
All Inclusive Full Day and Sunset Private Catamaran in St. Pete

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

8 hours Free Cancellation
from
$2,200
All Inclusive Full Day Luxury Catamaran Charter

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

7 hours Free Cancellation
5.0 (1)
from
$2,100
All Inclusive Half Day Sunset Catamaran Adventure

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

6 hours Free Cancellation
5.0 (1)
from
$2,000
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
All Inclusive St Pete Private Half Day Catamaran Charter

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

5 hours Free Cancellation
5.0 (1)
from
$1,700
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 Sailing Charter: Up to 24 Passengers

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco …More

Likely to Sell Out
Likely to Sell Out
San Francisco, USA

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco...

1 hour 30 minutes
5.0 (2)
from
$1,425
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
Private Sailing Tour -2 Hour (Up to 12 Passengers)

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double ended ketch. Inspired by the original designs of famed naval …More

San Diego, USA

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double ended ketch. Inspired by the original designs of famed naval...

2 hours Free Cancellation
from
$1,200
4th of July Sunset Sail on the Black Pearl

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The Black Pearl! Sail magestically across …More

Likely to Sell Out
Likely to Sell Out
Sandusky, USA

Join us for the 4th of July for Fireworks over Cedar Point from a beautiful 47' Sailing yacht - The Black Pearl! Sail magestically across...

4 to 5 hours
from
$1,195
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

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