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Top USA Sailing Trips

376 Results
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

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 …More

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 minutes Free Cancellation
4.6 (858)
from
$56
Daytime Charleston Harbor Sail - Lux Catamatan w/Bar

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to …More

Mount Pleasant, USA

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to...

2 hours Free Cancellation
4.7 (11)
from
$56
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

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 …More

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 minutes Free Cancellation
4.7 (564)
from
$55
Scenic Day Sails in Newport Harbor and Narragansett Bay Aquidneck

Set sail aboard Aquidneck on a memorable journey through Newport Harbor and Narragansett Bay, where the winds are perfect for an afternoon adventure. Guests can …More

Likely to Sell Out
Likely to Sell Out
Newport, USA

Set sail aboard Aquidneck on a memorable journey through Newport Harbor and Narragansett Bay, where the winds are perfect for an afternoon adventure. Guests can...

1 hour 40 minutes Free Cancellation
5.0 (4)
from
$55
San Diego Harbor Cruise on the Largest Catamaran in San Diego

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by …More

San Diego, USA

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by...

2 hours 30 minutes Free Cancellation
4.9 (55)
from
$55
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Shore Excursions TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for …More

Oahu, USA

2025 Cool Shore Excursions TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for...

2 hours Free Cancellation
4.9 (1,015)
from
$55
Sightseeing Day Sail around Boston Harbor

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of …More

Likely to Sell Out
Likely to Sell Out
Boston, USA

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of...

90 to 120 minutes Free Cancellation
4.8 (654)
from
$54
Seattle Sailing Harbor Tour

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 …More

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 hours Free Cancellation
4.8 (590)
from
$54
Sunset Cruise 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

Likely to Sell Out
Likely to Sell Out
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
5.0 (71)
from
$54
San Diego Whale Watching Cruise

Each year approximately 20,000 gray whales migrate from the Bering Sea to the lagoons of Baja California and back again. Come witness this amazing journey off …More

San Diego, USA

Each year approximately 20,000 gray whales migrate from the Bering Sea to the lagoons of Baja California and back again. Come witness this amazing journey off...

3 hours 30 minutes Free Cancellation
4.6 (681)
from
$54
Schooner Appledore Day Sail with Full Bar in Key West

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 …More

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 hours Free Cancellation
5.0 (113)
from
$54
Key West Reef Morning Snorkeling with Breakfast and Mimosas

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 …More

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 hours Free Cancellation
4.7 (694)
from
$54
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while …More

Oahu, USA

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while...

1 hour 30 minutes Free Cancellation
5.0 (13)
from
$53
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never …More

Oahu, USA

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never...

2 hours Free Cancellation
4.7 (1,265)
from
$53
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

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 …More

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 hours Free Cancellation
4.9 (5,050)
from
$52
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 (279)
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
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
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

Likely to Sell Out
Likely to Sell Out
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
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 (1,797)
from
$50

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