Top USA Sailing Trips

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
Likely to Sell Out
Likely to Sell Out
Fort Lauderdale, USA

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along...

1 hourFree Cancellation
1 hourFree Cancellation
1 hour • Free Cancellation
4.9 (1,520)
$35
$34

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor
Likely to Sell Out
Likely to Sell Out
Charleston, USA

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.6 (786)
$56
$55

Key West Signature Sunset Sail with Live Music, Open Bar & Food
Likely to Sell Out
Likely to Sell Out
Key West, USA

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.7 (403)
$72
$71

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
Special Offer
Special Offer
Panama City Beach, USA

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.9 (4,842)
$52.43
$51.43

Key West Dolphin and Snorkel Experience
Likely to Sell Out
Likely to Sell Out
Key West, USA

The Top10Adventures® Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.7 (337)
$69.95
$68.95

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Likely to Sell Out
Likely to Sell Out
Key West, USA

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (1,701)
$122.59
$121.59

Sunset Catamaran Cruise in Ft. Lauderdale
Special Offer
Special Offer
Fort Lauderdale, USA

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (696)
$129
$128

Key West Reef Morning Snorkeling with Breakfast and Mimosas
Special Offer
Special Offer
Key West, USA

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.7 (659)
$49.95
$48.95

Classic Tall Ship Cruise in Boston Harbor
Likely to Sell Out
Likely to Sell Out
Boston, USA

Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liberty Star or Fame. Get away from the...

90 to 120 minutesFree Cancellation
90 to 120 minutesFree Cancellation
90 to 120 minutes • Free Cancellation
4.8 (718)
$39.55
$38.55

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure
Likely to Sell Out
Likely to Sell Out
Oahu, USA

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard our either...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (1,437)
$80.71
$79.71

Seattle Sailing Harbor Tour
Likely to Sell Out
Likely to Sell Out
Seattle, USA

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (528)
$39
$38

Key West Reef Snorkel & Sail Adventure
Likely to Sell Out
Likely to Sell Out
Key West, USA

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.8 (542)
$79
$78

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
Special Offer
Special Offer
Panama City Beach, USA

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (2,005)
$52.43
$51.43

Sunset Dolphin Sail Aboard the Privateer Catamaran
Likely to Sell Out
Likely to Sell Out
Panama City Beach, USA

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer,...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (738)
$45
$44

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
Likely to Sell Out
Likely to Sell Out
Hilton Head Island, USA

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.7 (539)
$55
$54

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Special Offer
Special Offer
Oahu, USA

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (941)
$84.99
$83.99

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain
Special Offer
Special Offer
Bar Harbor, USA

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises....

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.2 (626)
$70
$69

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach
Likely to Sell Out
Likely to Sell Out
Clearwater, USA

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (275)
$80
$79

Sunset Sail in Key West with Beverages Included
Likely to Sell Out
Likely to Sell Out
Key West, USA

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (964)
$79
$78

Waikiki Sunset Cocktail Sail on the Moana Catamaran
Likely to Sell Out
Likely to Sell Out
Oahu, USA

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (2,315)
$89.99
$88.99

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