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Top 10 Best USA Sailing Trips

Found 431 Sailing Trips activities in USA. Sort by Popularity. - Page 9
 
-15% Polynesian Canoe Morning Sail

Polynesian Canoe Morning Sail

(5 of 18 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Special Offer
Free Cancellation
Start From $170.00
(Saving 15% ) $200.00
 
-15% Polynesian Canoe Morning Sail

Polynesian Canoe Morning Sail

  • USA
  • Superb18 reviews5

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Special Offer
    Free Cancellation
    Start From $170.00
    (Saving 15% ) $200.00
 
 

Chicago's Fireworks Show aboard Tall Ship Windy!

(4.8 of 14 reviews)

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More

Free Cancellation
Start From $113.73
 
Chicago's Fireworks Show aboard Tall Ship Windy! Likely to Sell Out

Chicago's Fireworks Show aboard Tall Ship Windy!

  • USA
  • Superb14 reviews4.8

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....

    Free Cancellation
    Start From $113.73
 
 

Fort Lauderdale Sailing Charter

(5 of 388 reviews)

You Embark on an unforgettable journey starting in Fort Lauderdale on our New River also known as the “Venice of America." The New River offers a blend of natural beauty, luxurious homes, and fascinating history. Your adventure ... More

Free Cancellation
Start From $150.00
 
Fort Lauderdale Sailing Charter Likely to Sell Out

Fort Lauderdale Sailing Charter

  • USA
  • Superb388 reviews5

You Embark on an unforgettable journey starting in Fort Lauderdale on our New River also known as th....

    Free Cancellation
    Start From $150.00
 
 

New York City Sunset Sail to the Statue of Liberty

(4.9 of 66 reviews)

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic sailboat is 105-feet in length and has about 3600 square feet of sail ... More

Free Cancellation
Start From $90.12
 
New York City Sunset Sail to the Statue of Liberty Likely to Sell Out

New York City Sunset Sail to the Statue of Liberty

  • USA
  • Superb66 reviews4.9

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....

    Free Cancellation
    Start From $90.12
 
 

Waikiki Fireworks Cocktail Cruise

(4.4 of 7 reviews)

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to remember. ... More

Free Cancellation
Start From $85.09
 
Waikiki Fireworks Cocktail Cruise Likely to Sell Out

Waikiki Fireworks Cocktail Cruise

  • USA
  • Exellent7 reviews4.4

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....

    Free Cancellation
    Start From $85.09
 
 

Private Sailing on the Miami Bay - Biscayne Bay

(4.9 of 75 reviews)

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish vessels in the company of experienced, but mostly fun, well traveled, passionate captains. A Private Sailing tour aboard Destino ... More

Free Cancellation
Private Tour
Start From $425.00
 
Private Sailing on the Miami Bay - Biscayne Bay Likely to Sell Out

Private Sailing on the Miami Bay - Biscayne Bay

  • USA
  • Superb75 reviews4.9

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish....

    Free Cancellation
    Private Tour
    Start From $425.00
 
 

Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!

(5 of 126 reviews)

Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in the Puget Sound. This personalized voyage is designed for up to six passengers, offering an intimate and unforgettable experience ... More

Free Cancellation
Private Tour
Start From $549.00
 
Seattle's Best Private Sailing Adventure on the Puget Sound BYOB! Likely to Sell Out

Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!

  • USA
  • Superb126 reviews5

Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in ....

    Free Cancellation
    Private Tour
    Start From $549.00
 
 

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

(4.6 of 126 reviews)

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More

Free Cancellation
Private Tour
Start From $54.95
 
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor Likely to Sell Out

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

  • USA
  • Superb126 reviews4.6

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Private Tour
    Start From $54.95
 
 

Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

(5 of 14 reviews)

What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery + Cafe. F... More

Free Cancellation
Private Tour
Start From $84.75
 
Pastries & Prosecco Aboard a Tall Ship in Boston Harbor Likely to Sell Out

Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

  • USA
  • Superb14 reviews5

What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable v....

    Free Cancellation
    Private Tour
    Start From $84.75
 
 

Newport Sunset Sail on Classic Sailboat

(4.8 of 42 reviews)

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More

Free Cancellation
Private Tour
Start From $67.84
 
Newport Sunset Sail on Classic Sailboat Likely to Sell Out

Newport Sunset Sail on Classic Sailboat

  • USA
  • Superb42 reviews4.8

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....

    Free Cancellation
    Private Tour
    Start From $67.84
 
 

Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15

(4.5 of 31 reviews)

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More

Free Cancellation
Private Tour
Start From $60.00
 
Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15 Likely to Sell Out

Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15

  • USA
  • Exellent31 reviews4.5

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Free Cancellation
    Private Tour
    Start From $60.00
 
 

Chicago Air and Water Show VIP Cruise or Skydeck Experience

(5 of 2 reviews)

Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chicago’s Air & Water Show from the Best Seat on the Lake! 10AM SAIL: Our first sail will depart at 10am sharp. Our first event wil... More

Free Cancellation
Private Tour
Start From $154.00
 
Chicago Air and Water Show VIP Cruise or Skydeck Experience Likely to Sell Out

Chicago Air and Water Show VIP Cruise or Skydeck Experience

  • USA
  • Superb2 reviews5

Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chic....

    Free Cancellation
    Private Tour
    Start From $154.00
 
 

2.5 hr Sailboat Tour aboard Orion's Child

(5 of 73 reviews)

TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple daily sails that include a quarter day and sunset sail aboard a ... More

Free Cancellation
Private Tour
Start From $130.00
 
2.5 hr Sailboat Tour aboard Orion's Child Likely to Sell Out

2.5 hr Sailboat Tour aboard Orion's Child

  • USA
  • Superb73 reviews5

TripAdvisor Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer t....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

(5 of 73 reviews)

Set sail on Maui's only floating tiki bar aboard a hand-built catamaran, where sunsets and handcrafted cocktails create unforgettable memories. Enjoy a relaxing evening of island tunes, light snacks, and an open bar as you glide o... More

Free Cancellation
Private Tour
Start From $119.56
 
Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran Likely to Sell Out

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

  • USA
  • Superb73 reviews5

Set sail on Maui's only floating tiki bar aboard a hand-built catamaran, where sunsets and handcraft....

    Free Cancellation
    Private Tour
    Start From $119.56
 
 

Private Sunset Catamaran Sail in Cocoa Beach

(5 of 73 reviews)

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the bea... More

Free Cancellation
Private Tour
Start From $337.87
 
Private Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Private Sunset Catamaran Sail in Cocoa Beach

  • USA
  • Superb73 reviews5

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a....

    Free Cancellation
    Private Tour
    Start From $337.87
 
 

2-Hour Private Sailboat Charter in the San Francisco Bay

(4.9 of 21 reviews)

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 romance of sail. Private sailboat charters are a great way to celebrate you... More

Free Cancellation
Private Tour
Start From $695.00
 
2-Hour Private Sailboat Charter in the San Francisco Bay Likely to Sell Out

2-Hour Private Sailboat Charter in the San Francisco Bay

  • USA
  • Superb21 reviews4.9

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Jus....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

(5 of 118 reviews)

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy with some goo... More

Free Cancellation
Private Tour
Start From $525.00
 
Private Hilton Head Sunset Sailing Tour with Dolphin Watching Likely to Sell Out

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

  • USA
  • Superb118 reviews5

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

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 21 reviews)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Charter in Waikiki (1-6 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (1-6 Guests)

  • USA
  • Superb21 reviews5

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

Brunch Cruise with Buffet in Washington

(4 of 10 reviews)

Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer three public sailing tours daily from Seattle’s downtown waterfront. Our beautiful sailing ship, the Bay Lady, evokes the romanc... More

Free Cancellation
Private Tour
Start From $89.00
 
Brunch Cruise with Buffet in Washington Likely to Sell Out

Brunch Cruise with Buffet in Washington

  • USA
  • Very Good10 reviews4

Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Private Guided Sunset and Eco Tour up to 6 Passengers

(5 of 74 reviews)

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 from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More

Free Cancellation
Private Tour
Start From $249.99
 
Private Guided Sunset and Eco Tour up to 6 Passengers Likely to Sell Out

Private Guided Sunset and Eco Tour up to 6 Passengers

  • USA
  • Superb74 reviews5

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

    Free Cancellation
    Private Tour
    Start From $249.99
 
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