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Top USA Sailing Trips

375 Results
Fort Myers: Tiki Pub VIP Private Dolphin & Sunset Cruise

Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. Whether you want to …More

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

Spend the most amazing time of day in the best place to enjoy it. Our custom tiki boat has it all. Whether you want to...

2 hours Free Cancellation
5.0 (4)
from
$449
Private Sunset and Eco Tour in Destin Up to 18 Guests

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset...

1 hour 30 minutes Free Cancellation
5.0 (45)
from
$450
Marco Island Private Catamaran Sailing Tour

It’s your own private sail with Captain Nick, the owner of Easy Breezy Charters. Breezy is a 30-foot Stiletto sailing catamaran with open nets at …More

Likely to Sell Out
Likely to Sell Out
Naples, USA

It’s your own private sail with Captain Nick, the owner of Easy Breezy Charters. Breezy is a 30-foot Stiletto sailing catamaran with open nets at...

2 hours
5.0 (154)
from
$450
Private Sailing Charters in Oceanside CA

Explore the stunning Pacific waters with a private sailing charter in Oceanside, California. Enjoy a customizable sailing adventure tailored to your pace and interests, guided …More

Carlsbad, USA

Explore the stunning Pacific waters with a private sailing charter in Oceanside, California. Enjoy a customizable sailing adventure tailored to your pace and interests, guided...

2 hours Free Cancellation
5.0 (4)
from
$450
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed …More

Oahu, USA

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed...

2 hours Free Cancellation
5.0 (4)
from
$450
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

Likely to Sell Out
Likely to Sell Out
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
Private Catamaran: Snorkel, Swim and Dolphin Watching

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take...

3 hours Free Cancellation
5.0 (1)
from
$465
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the …More

Hilton Head Island, USA

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the...

2 hours Free Cancellation
5.0 (121)
from
$485
Private Sailing Charter on San Diego Bay

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural …More

San Diego, USA

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural...

3 hours Free Cancellation
4.9 (50)
from
$499
Best Private Luxury Daytime Boat Tour in New York City - 2 Hour

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view …More

New York City, USA

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view...

2 hours Free Cancellation
5.0 (99)
from
$500
Private Sailing Charter with Captain, BYOB

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's …More

Charleston, USA

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's...

2 hours 30 minutes Free Cancellation
5.0 (96)
from
$500
San Diego Wild Life Sailing Adventure Private

Join GoSailing San Diego for a private 4-hour wildlife sail aboard Wolf, a classic 1967 Cal 34 sailboat, with Captain Sal and First Mate Sharon. …More

San Diego, USA

Join GoSailing San Diego for a private 4-hour wildlife sail aboard Wolf, a classic 1967 Cal 34 sailboat, with Captain Sal and First Mate Sharon....

4 hours Free Cancellation
5.0 (2)
from
$503
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
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 (430)
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
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
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
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

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