USA Sailing Trips

377 Results
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
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 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 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
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 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 City Balloon Tours …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 City Balloon Tours...

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
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 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 City Balloon Tours …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 City Balloon Tours...

2 to 4 hours Free Cancellation
5.0 (35)
from
$575
Private Daytime Sailing Cruise on Lake Champlain (6 Passengers)

Enjoy a sailing experience like no other as you cruise Lake Champlain guided entirely by the wind—making every journey unique. Along the way, your captain …More

Likely to Sell Out
Likely to Sell Out
Burlington, USA

Enjoy a sailing experience like no other as you cruise Lake Champlain guided entirely by the wind—making every journey unique. Along the way, your captain...

2 hours
5.0 (11)
from
$550
Private Daytime Picnic Boat Cruise (Up to 6 Passengers)

Set sail on Lake Champlain for a one-of-a-kind adventure where the route is guided entirely by the wind—ensuring no two cruises are ever the same. …More

Likely to Sell Out
Likely to Sell Out
Burlington, USA

Set sail on Lake Champlain for a one-of-a-kind adventure where the route is guided entirely by the wind—ensuring no two cruises are ever the same....

2 hours
5.0 (2)
from
$550
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
Spend the Day on Buzzards Bay - Powerboat Cruises

Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per hour for a two-hour trip. Up to 6 passengers are …More

Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per hour for a two-hour trip. Up to 6 passengers are...

2 hours Free Cancellation
5.0 (1)
from
$540
2.5 Hour Karaoke Cruise Experience in Lake Chatuge

Join us for an amazing karaoke cruise across the gorgeous waters of Lake Chatuge! Belt out your favorite tunes or just kick back and enjoy …More

Join us for an amazing karaoke cruise across the gorgeous waters of Lake Chatuge! Belt out your favorite tunes or just kick back and enjoy...

3 hours Free Cancellation
5.0 (1)
from
$530
Private Luxury Yacht Charters, BYOB & Dolphins

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the …More

Charleston, USA

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the...

2 hours 30 minutes Free Cancellation
5.0 (431)
from
$525
Private Hilton Head Sunset Sailing Tour with Dolphin Watching

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - …More

Hilton Head Island, USA

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island -...

2 hours Free Cancellation
5.0 (125)
from
$525
Private Morning Sail, Dolphin and History Tour on Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing …More

Charleston, USA

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing...

2 hours Free Cancellation
5.0 (86)
from
$525
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed...

2 hours Free Cancellation
5.0 (71)
from
$508

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