Top USA Sailing Trips

All Inclusive Full Day and Sunset Private Catamaran in St. Pete
Special Offer
Special Offer
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 hoursFree Cancellation
8 hoursFree Cancellation
8 hours • Free Cancellation
$2,200
$2,199

All Inclusive Full Day Luxury Catamaran Charter
Special Offer
Special Offer
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 hoursFree Cancellation
7 hoursFree Cancellation
7 hours • Free Cancellation
$2,100
$2,099

All Inclusive Half Day Sunset Catamaran Adventure
Special Offer
Special Offer
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 hoursFree Cancellation
6 hoursFree Cancellation
6 hours • Free Cancellation
$2,000
$1,999

3 Hour Luxury Private Sailing Catamaran for 7-12 People
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 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
$1,995
$1,994

Private Charter: Shell Island Snorkeling & Dolphin Adventure
Likely to Sell Out
Likely to Sell Out
Panama City Beach, USA

What makes this experience truly special is that it is a private charter designed entirely around your group. Unlike crowded tours with fixed schedules, this...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.8 (31)
$1,900
$1,899

South Beach Miami BACHELORETTE Boat Day!
Special Offer
Special Offer
Miami, USA

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and best marina in SOUTH BEACH... We've found the...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (1)
$1,795
$1,794

All Inclusive St Pete Private Half Day Catamaran Charter
Special Offer
Special Offer
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 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
$1,700
$1,699

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
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 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (1)
$1,595
$1,594

Private Afternoon Harbor Cruise on Kismet for parties up to 20
Special Offer
Special Offer
Charleston, USA

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (29)
$1,549
$1,548

2hr Luxury Private Sailing Catamaran for 7-12 People
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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (3)
$1,495
$1,494

Private Oahu Sunset Charter with Tasting and Drinks
Special Offer
Special Offer
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 minutesFree Cancellation
120 to 150 minutesFree Cancellation
120 to 150 minutes • Free Cancellation
5.0 (50)
$1,413.61
$1,412.61

Luxury Diamond Head Sunset Sail
Special Offer
Special Offer
Oahu, USA

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (3)
$1,398
$1,397

Private Sailing Charter: Up to 24 Passengers
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 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (1)
$1,207.50
$1,206.50

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (2)
$1,200
$1,199

Wrightsville Beach Day Sail Private Catamaran Charter
Likely to Sell Out
Likely to Sell Out
Wilmington, USA

On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islands and local spots. Upon anchoring, the crew...

4 hours
4 hours
4 hours
5.0 (1)
$1,200
$1,199

Private Sailing Tour -2 Hour (Up to 12 Passengers)
Special Offer
Special Offer
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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
$1,200
$1,199

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure
Special Offer
Special Offer
Oahu, USA

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience is amazing for you to relax and have fun....

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (3)
$1,199
$1,198

Private Sunset Yacht Cruise | Champagne Included | San Diego Bay
Special Offer
Special Offer
San Diego, USA

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
$1,199
$1,198

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (14)
$1,150
$1,149

Navy Pier Chicago: Private Sailboat Charter with Captain
Likely to Sell Out
Likely to Sell Out
Chicago, USA

On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate attention...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
$1,099
$1,098

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