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Top USA Sailing Trips

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

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 hours Free Cancellation
5.0 (113)
from
$54
Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear...

2 hours 30 minutes Free Cancellation
4.8 (42)
from
$127
2-Hour Relaxing Chesapeake Day Sail on Lady Patty

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in …More

Likely to Sell Out
Likely to Sell Out

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in...

2 hours Free Cancellation
5.0 (22)
from
$160
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, …More

Oahu, USA

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night,...

1 hour Free Cancellation
4.8 (62)
from
$90
2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions …More

Hilton Head Island, USA

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions...

2 hours Free Cancellation
5.0 (37)
from
$465
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea,...

2 hours Free Cancellation
4.8 (19)
from
$279
Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also …More

Charleston, USA

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also...

2 to 4 hours Free Cancellation
5.0 (56)
from
$599
Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples...

2 hours Free Cancellation
5.0 (17)
from
$300
Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step …More

Maui, USA

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes Free Cancellation
4.8 (63)
from
$249
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
Private Day Sail in San Diego up to 12 guests

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San …More

San Diego, USA

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San...

2 hours 30 minutes Free Cancellation
5.0 (70)
from
$81
Private Sunset Sail in San Diego Up to 6 guests

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking …More

La Jolla, USA

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking...

2 hours Free Cancellation
5.0 (74)
from
$99
Tiki Pub Glow Party Cruise (Adults only)

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic...

2 hours Free Cancellation
4.9 (18)
from
$90
2 Hour Chesapeake Day Sail on Catamaran Epiphany

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel …More

Likely to Sell Out
Likely to Sell Out

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel...

2 hours Free Cancellation
5.0 (17)
from
$245
Private Key West Sandbar and Paddle by Boat

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats...

3 hours 30 minutes Free Cancellation
5.0 (38)
from
$600
St Augustine Nights of Lights Viewing Boat with Live Music

See St. Augustine's Nights of Lights from the water on an evening cruise with live music, drinks, snacks and holiday cookies: choose a 2-hour sunset …More

St Augustine, USA

See St. Augustine's Nights of Lights from the water on an evening cruise with live music, drinks, snacks and holiday cookies: choose a 2-hour sunset...

1 hour 45 minutes (Approx.) Free Cancellation
4.9 (64)
from
$72
Golden Gate Bridge Sailing Tour

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views …More

San Francisco, USA

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views...

2 hours Free Cancellation
4.9 (52)
from
$129
Baltimore History Sail on the Summer Wind

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the …More

Baltimore, USA

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the...

1 hour 30 minutes Free Cancellation
4.9 (72)
from
$65
New York City Live Jazz Sail

Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around …More

Likely to Sell Out
Likely to Sell Out
New York City, USA

Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around...

2 hours Free Cancellation
4.9 (15)
from
$134
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

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