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Top USA Sailing Trips

375 Results
Captain Steve's Sailing Experience on Long Island

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience, …More

Long Island, USA

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience,...

2 hours
5.0 (11)
from
$550
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Cool Shore Excursions …More

Charleston, USA

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Cool Shore Excursions...

2 to 4 hours Free Cancellation
5.0 (35)
from
$575
Sunset Sail on the Black Pearl

Come experience the tranquility of gliding through the water under sail on the Black Pearl while appreciating our beautiful Lake Erie sunsets. See Cedar Point …More

Sandusky, USA

Come experience the tranquility of gliding through the water under sail on the Black Pearl while appreciating our beautiful Lake Erie sunsets. See Cedar Point...

2 hours Free Cancellation
4.4 (7)
from
$595
Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

Sail the Charleston Harbor, see dolphins, amazing sunsets 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, amazing sunsets 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 (40)
from
$599
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Cool Shore Excursions …More

Likely to Sell Out
Likely to Sell Out
Charleston, USA

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Cool Shore Excursions...

2 to 4 hours Free Cancellation
5.0 (62)
from
$599
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 (57)
from
$599
Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything …More

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

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything...

3 hours Free Cancellation
5.0 (2)
from
$599
Best Private Luxury Sunset Boat Tour in New York City - 2 Hour

Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and reflects off of the city skyline on …More

New York City, USA

Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and reflects off of the city skyline on...

2 hours Free Cancellation
5.0 (29)
from
$600
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
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment …More

Miami, USA

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment...

3 to 30 minutes Free Cancellation
4.9 (12)
from
$600
Private Sailing Charter in Brooklyn

Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adventure waiting for you! Departing from Brooklyn …More

Likely to Sell Out
Likely to Sell Out
Brooklyn, USA

Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adventure waiting for you! Departing from Brooklyn...

2 hours Free Cancellation
5.0 (9)
from
$630
Private Charter: Shell Island Snorkeling & Dolphin Adventure

What makes this experience truly special is that it is a private charter designed entirely around your group. Unlike crowded tours with fixed schedules, this …More

Panama City Beach, USA

What makes this experience truly special is that it is a private charter designed entirely around your group. Unlike crowded tours with fixed schedules, this...

3 hours Free Cancellation
4.8 (32)
from
$641
Private Sailing Charter in Savannah GA

Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whether it's a family outing, an intimate wedding, …More

Savannah, USA

Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whether it's a family outing, an intimate wedding,...

2 hours Free Cancellation
5.0 (7)
from
$650
Private Sail Around New York City and The Statue of Liberty

Discover NYC from a completely different perspective on a private sailboat charter. You and your group will view New York City in ways that are …More

Jersey City, USA

Discover NYC from a completely different perspective on a private sailboat charter. You and your group will view New York City in ways that are...

2 hours Free Cancellation
5.0 (10)
from
$650
Oyster Bay Two Hour Sailing Experience

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and …More

Long Island, USA

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and...

2 hours Free Cancellation
5.0 (2)
from
$650
2-Hour Private Sailing Experience in San Diego Bay

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing...

2 hours Free Cancellation
5.0 (188)
from
$675
Private Key West Sunset Sail

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for …More

Key West, USA

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for...

2 hours
4.9 (50)
from
$693
2 Hours Private Sailboat Charter in the San Francisco Bay

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the …More

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

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the...

2 hours Free Cancellation
4.8 (22)
from
$695
Private Boat Charter to Johns Pass Shell Key and Egmont Key

Cruise the beautiful waters of the Tampa Bay area on a private boat charter customized to your group. Explore popular destinations such as Shell Key, …More

St Petersburg, USA

Cruise the beautiful waters of the Tampa Bay area on a private boat charter customized to your group. Explore popular destinations such as Shell Key,...

4 hours Free Cancellation
5.0 (4)
from
$695
Private Classic Sailboat Tour in New York City

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll …More

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

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll...

2 hours Free Cancellation
5.0 (4)
from
$700

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