Top USA Sailing Trips

City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour
Special Offer
Special Offer
San Diego, USA

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, this journey takes you past iconic landmarks such...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.6 (512)
$34.85
$33.85

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach
Likely to Sell Out
Likely to Sell Out
Clearwater, USA

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.7 (62)
$34.95
$33.95

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

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

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

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island,...

1 hourFree Cancellation
1 hourFree Cancellation
1 hour • Free Cancellation
4.6 (345)
$39
$38

Escape from the Rock! Cruise around Alcatraz
Likely to Sell Out
Likely to Sell Out
San Francisco, USA

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.4 (142)
$39
$38

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

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran
Likely to Sell Out
Likely to Sell Out
Panama City Beach, USA

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip through Grand Lagoon and along the coast of...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (6)
$40
$39

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

Sunset Dolphin Sail Aboard the Footloose 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 SV Footloose, our...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (466)
$45
$44

Waikiki Sunset Cruise from Oahu
Special Offer
Special Offer
Oahu, USA

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (66)
$45
$44

South Shore Open Sail from Kewalo Harbor Including Drinks
Special Offer
Special Offer
Oahu, USA

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (25)
$47.50
$46.50

Sailing on Historic Schooner Yacht in Salem, MA
Special Offer
Special Offer
Salem, USA

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X....

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (211)
$47.81
$46.81

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
Likely to Sell Out
Likely to Sell Out
Hilton Head Island, USA

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (704)
$47.99
$46.99

Sunset Cruise Tour
Special Offer
Special Offer
Naples, USA

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (58)
$48.50
$47.50

Schooner Appledore Day Sail with Full Bar in Key West
Likely to Sell Out
Likely to Sell Out
Key West, USA

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (113)
$49
$48

Sunset sail Aboard Manakai Catamaran
Likely to Sell Out
Likely to Sell Out
Oahu, USA

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (23)
$49.82
$48.82

Tiki Pub Amazing Dolphin Eco Adventure
Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (8)
$49.95
$48.95

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
Special Offer
Special Offer
Oahu, USA

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (255)
$49.99
$48.99

Waikiki Sunset Boat Cruise
Likely to Sell Out
Likely to Sell Out
Oahu, USA

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (202)
$50
$49

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