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Top 10 Best USA Sailing Trips

Found 399 Sailing Trips activities in USA. Sort by Popularity. - Page 10
 

Suncoast Sailing's Day Sailing Experience!

(4.9 of 102 reviews)

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. Feel the wind as it glides us through the picturesque waters of Treasure Island and Gulf of Mexico. Come face to face with nature a... More

Free Cancellation
Start From $59.99
 
Suncoast Sailing's Day Sailing Experience!

Suncoast Sailing's Day Sailing Experience!

  • USA
  • Superb102 reviews4.9

Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. F....

    Free Cancellation
    Start From $59.99
 
 

Shared Day Sail along Historic St Augustine Bayfront

(5 of 4 reviews)

Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories on the sea. Our cruise is perfect for all water-lovers: families, couples, and friends. Some guests interact with the USCG licensed... More

Free Cancellation
Start From $129.00
 
Shared Day Sail along Historic St Augustine Bayfront Likely to Sell Out

Shared Day Sail along Historic St Augustine Bayfront

  • USA
  • Superb4 reviews5

Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories o....

    Free Cancellation
    Start From $129.00
 
 

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

(5 of 25 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor since 2012, our sailing yachts are the highest quality and operated ... More

Free Cancellation
Private Tour
Start From $525.00
 
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique Likely to Sell Out

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

  • USA
  • Superb25 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Deluxe Day Sail in San Diego

(5 of 48 reviews)

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More

Free Cancellation
Private Tour
Start From $119.00
 
Deluxe Day Sail in San Diego Likely to Sell Out

Deluxe Day Sail in San Diego

  • USA
  • Superb48 reviews5

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

(4.7 of 7 reviews)

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More

Free Cancellation
Private Tour
Start From $63.00
 
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms Likely to Sell Out

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

  • USA
  • Superb7 reviews4.7

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....

    Free Cancellation
    Private Tour
    Start From $63.00
 
 

2.5-hour Guided Sailboat Tour

(4.9 of 172 reviews)

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, 159 Bridge Park Drive. Views of the Brooklyn Bridge, Statue of Liberty, World Trade Center, Ellis Island, Governor's Island and M... More

Free Cancellation
Private Tour
Start From $118.00
 
2.5-hour Guided Sailboat Tour Likely to Sell Out

2.5-hour Guided Sailboat Tour

  • USA
  • Superb172 reviews4.9

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, ....

    Free Cancellation
    Private Tour
    Start From $118.00
 
 

Sailing Charter

(4.9 of 172 reviews)

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend out of scenic Sequim Bay! Ingrid Princess is an ocean going, full keel ketch avail... More

Free Cancellation
Private Tour
Start From $195.00
 
Sailing Charter Likely to Sell Out

Sailing Charter

  • USA
  • Superb172 reviews4.9

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....

    Free Cancellation
    Private Tour
    Start From $195.00
 
 

Luxury Catamaran Whale Watch

(5 of 40 reviews)

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback whale. The waters off West Maui have long been the favored vacation spot of these massive marine mammals. The Alii Class Yachts pro... More

Free Cancellation
Private Tour
Start From $159.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • USA
  • Superb40 reviews5

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback w....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Statue of Liberty Sunset Cruise and New York City Sky Line

(3.1 of 39 reviews)

New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View of the Manhattan skyline, One World Trade Center and the Empire State Building.Enjoy a panoramic view of lower Manhattan as you p... More

Free Cancellation
Private Tour
Start From $35.00
 
Statue of Liberty Sunset Cruise and New York City Sky Line Likely to Sell Out

Statue of Liberty Sunset Cruise and New York City Sky Line

  • USA
  • Good39 reviews3.1

New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

2 Hour Rosé Luxury Day Sail

(3.1 of 39 reviews)

This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expert captains leading the way. Keep an eye out for dolphins, seabirds, and Lowcountry landmarks as you relax, unwind, and enjoy the ... More

Free Cancellation
Private Tour
Start From $74.97
 
2 Hour Rosé Luxury Day Sail Likely to Sell Out

2 Hour Rosé Luxury Day Sail

  • USA
  • Good39 reviews3.1

This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expe....

    Free Cancellation
    Private Tour
    Start From $74.97
 
 

Condor Sailing Public Dolphin and Sightseeing Cruise

(4.4 of 7 reviews)

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More

Free Cancellation
Private Tour
Start From $104.00
 
Condor Sailing Public Dolphin and Sightseeing Cruise Likely to Sell Out

Condor Sailing Public Dolphin and Sightseeing Cruise

  • USA
  • Exellent7 reviews4.4

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....

    Free Cancellation
    Private Tour
    Start From $104.00
 
 

Schooner Fame Sailing Tour

(4.9 of 524 reviews)

FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per TripAdvisor. Don't miss the very best of what Salem has to offer! There's more to our town than witches! FAME is a full-scale replica... More

Free Cancellation
Private Tour
Start From $45.46
 
Schooner Fame Sailing Tour Likely to Sell Out

Schooner Fame Sailing Tour

  • USA
  • Superb524 reviews4.9

FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per Trip....

    Free Cancellation
    Private Tour
    Start From $45.46
 
 

Sail Bainbridge Island & Seattle Waters - Luxury Classic Sailboat

(5 of 26 reviews)

Sailing Puget Sound is an unforgettable experience! We’ll set sail & soak up the panorama of these beautiful & inspiring waters. Departing daily from Bainbridge Island, a 30 min ferry ride from Seattle. This 2hr private sailing... More

Free Cancellation
Private Tour
Start From $475.00
 
Sail Bainbridge Island & Seattle Waters - Luxury Classic Sailboat Likely to Sell Out

Sail Bainbridge Island & Seattle Waters - Luxury Classic Sailboat

  • USA
  • Superb26 reviews5

Sailing Puget Sound is an unforgettable experience! We’ll set sail & soak up the panorama of these....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

(4.9 of 41 reviews)

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 the largest and nicest sailing yacht available for Charter in Charleston, kn... More

Free Cancellation
Private Tour
Start From $760.00
 
Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB Likely to Sell Out

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

  • USA
  • Superb41 reviews4.9

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht ....

    Free Cancellation
    Private Tour
    Start From $760.00
 
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.7 of 131 reviews)

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Private Tour
Start From $79.00
 
Key West Sailing & Snorkeling: A Reef Adventure Likely to Sell Out

Key West Sailing & Snorkeling: A Reef Adventure

  • USA
  • Superb131 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Private Catamaran Charter in Waikiki (7-12 Guests)

(4.7 of 131 reviews)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Private Catamaran Charter in Waikiki (7-12 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (7-12 Guests)

  • USA
  • Superb131 reviews4.7

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

(5 of 14 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on ou... More

Free Cancellation
Private Tour
Start From $89.00
 
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise Likely to Sell Out

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

  • USA
  • Superb14 reviews5

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Private Local Day Sail by a Certified Captain

(5 of 14 reviews)

Nominated Best of Baltimore Tourist Attraction 2023 & 2024 Baltimore’s authentic and top-rated private sailing experience awaits aboard Saeda, a 45-foot yacht offering a 2-hour daytime cruise through South Baltimore’s scenic ... More

Free Cancellation
Private Tour
Start From $735.00
 
Private Local Day Sail by a Certified Captain Likely to Sell Out

Private Local Day Sail by a Certified Captain

  • USA
  • Superb14 reviews5

Nominated Best of Baltimore Tourist Attraction 2023 & 2024 Baltimore’s authentic and top-rated pr....

    Free Cancellation
    Private Tour
    Start From $735.00
 
 

SUNSET CRUISE in Key Largo,FL.

(5 of 3 reviews)

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting in long lines. Personalize the trip to your liking. A private charter makes it more personab... More

Free Cancellation
Private Tour
Start From $479.00
 
SUNSET CRUISE in Key Largo,FL. Likely to Sell Out

SUNSET CRUISE in Key Largo,FL.

  • USA
  • Superb3 reviews5

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need t....

    Free Cancellation
    Private Tour
    Start From $479.00
 
 

Private Sailing Tour through the Ten Thousands Islands

(4.9 of 140 reviews)

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More

Free Cancellation
Private Tour
Start From $440.00
 
Private Sailing Tour through the Ten Thousands Islands Likely to Sell Out

Private Sailing Tour through the Ten Thousands Islands

  • USA
  • Superb140 reviews4.9

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....

    Free Cancellation
    Private Tour
    Start From $440.00
 
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