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Top USA Sailing Trips

376 Results
1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

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 …More

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 hour Free Cancellation
4.9 (1,532)
from
$35
Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in …More

Likely to Sell Out
Likely to Sell Out
Mount Pleasant, USA

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in...

2 hours Free Cancellation
5.0 (2)
from
$38
City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

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 …More

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 minutes Free Cancellation
4.6 (549)
from
$38
Sunset Dolphin Sail Aboard the Footloose Catamaran

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 …More

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 minutes Free Cancellation
4.9 (474)
from
$38
San Francisco Bay Cruise

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, …More

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 hour Free Cancellation
4.6 (388)
from
$39
Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

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

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 hours Free Cancellation
4.9 (2,096)
from
$42
Sunset Dolphin Sail Aboard the Privateer Catamaran

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, …More

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 hours Free Cancellation
4.8 (750)
from
$43
Afternoon Sightseeing and Sailing Tour

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 …More

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 hours Free Cancellation
4.9 (36)
from
$43
Waikiki Sunset Cruise from Oahu

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 …More

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 hours Free Cancellation
4.8 (76)
from
$45
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle, …More

Oahu, USA

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle,...

1 hour 30 minutes Free Cancellation
4.9 (256)
from
$45
South Shore Open Sail from Kewalo Harbor Including Drinks

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 …More

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 minutes Free Cancellation
4.8 (26)
from
$48
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

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 …More

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 minutes Free Cancellation
4.9 (720)
from
$48
Escape from the Rock! Cruise around Alcatraz

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 …More

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 minutes Free Cancellation
4.5 (146)
from
$48
Sunset sail Aboard Manakai Catamaran

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 …More

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 minutes Free Cancellation
5.0 (26)
from
$50
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Experience one Cool Shore Excursions's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from …More

Oahu, USA

Experience one Cool Shore Excursions's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from...

2 hours Free Cancellation
4.9 (1,795)
from
$50
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

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 …More

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 hours Free Cancellation
4.9 (264)
from
$50
Schooner Aquidneck Morning Mimosa Sail

Rise and Shine! There’s no better way to start your day in Newport than sailing past stunning sights while sipping a cool Mimosa aboard the …More

Newport, USA

Rise and Shine! There’s no better way to start your day in Newport than sailing past stunning sights while sipping a cool Mimosa aboard the...

1 hour 40 minutes Free Cancellation
5.0 (15)
from
$50
Dolphin Adventure Sail in Cocoa Beach

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide …More

Likely to Sell Out
Likely to Sell Out
Cocoa Beach, USA

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide...

2 hours Free Cancellation
4.9 (243)
from
$51
Waikiki Sunset Cruise: 2-Hour Catamaran & Swim Adventure in Oahu

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the...

2 hours Free Cancellation
4.8 (600)
from
$51
Waikiki Sunset Boat Cruise

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 …More

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 minutes Free Cancellation
5.0 (276)
from
$51

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