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Top 10 Best USA Sailing Trips

Found 448 Sailing Trips activities in USA. Sort by Popularity. - Page 14
 

Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

(5 of 40 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 $599.00
 
Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

  • USA
  • Superb40 reviews5

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

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

New York City Skyline Night Sailboat Tour

(5 of 13 reviews)

Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New York. See the New York City skyline, the Statue of Liberty and Ellis Island lit up at night. Sit back and relax while enjoying a pe... More

Free Cancellation
Private Tour
Start From $67.01
 
New York City Skyline Night Sailboat Tour Likely to Sell Out

New York City Skyline Night Sailboat Tour

  • USA
  • Superb13 reviews5

Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New Y....

    Free Cancellation
    Private Tour
    Start From $67.01
 
 

Fort Lauderdale Sailing Charter

(5 of 396 reviews)

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a beautiful blend of natural mangroves, luxurious waterfront homes, and ... More

Free Cancellation
Private Tour
Start From $200.00
 
Fort Lauderdale Sailing Charter Likely to Sell Out

Fort Lauderdale Sailing Charter

  • USA
  • Superb396 reviews5

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called....

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

(5 of 123 reviews)

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 North side of the island. During the day, this is generally filled with exciting winds for gre... More

Free Cancellation
Private Tour
Start From $485.00
 
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail Likely to Sell Out

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

  • USA
  • Superb123 reviews5

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind....

    Free Cancellation
    Private Tour
    Start From $485.00
 
 

Golden Gate Bridge Sailing Tour

(4.8 of 53 reviews)

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views of the San Francisco skyline, Sausalito, Angel Island, Tiburon, and Marin... More

Free Cancellation
Private Tour
Start From $129.00
 
Golden Gate Bridge Sailing Tour Likely to Sell Out

Golden Gate Bridge Sailing Tour

  • USA
  • Superb53 reviews4.8

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

(5 of 1 review)

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for fu... More

Free Cancellation
Private Tour
Start From $120.00
 
Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams Likely to Sell Out

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

  • USA
  • Superb1 review5

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Luxury Diamond Head Sunset Sail

(5 of 3 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private 50' luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from... More

Free Cancellation
Private Tour
Start From $1,398.00
 
Luxury Diamond Head Sunset Sail Likely to Sell Out

Luxury Diamond Head Sunset Sail

  • USA
  • Superb3 reviews5

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $1,398.00
 
 

LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

(4.3 of 4 reviews)

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and the Captain. Enjoy a stunning 1 hr private romantic night cruise and sea life discovery aboard... More

Free Cancellation
Private Tour
Start From $268.00
 
LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl Likely to Sell Out

LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

  • USA
  • Exellent4 reviews4.3

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht....

    Free Cancellation
    Private Tour
    Start From $268.00
 
 

Afternoon Ali'i Adventure

(5 of 6 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Free Cancellation
Private Tour
Start From $276.00
 
Afternoon Ali'i Adventure Likely to Sell Out

Afternoon Ali'i Adventure

  • USA
  • Superb6 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Free Cancellation
    Private Tour
    Start From $276.00
 
 

New York Day Sail to the Statue of Liberty on Schooner America

(4.8 of 65 reviews)

Offering a premium sailing experience, the Schooner America is a tribute to the original America that won the America's Cup in 1851. This classic sailboat is comfortable, elegant and smooth at 105-feet in length with 3600 square... More

Free Cancellation
Private Tour
Start From $60.08
 
New York Day Sail to the Statue of Liberty on Schooner America Likely to Sell Out

New York Day Sail to the Statue of Liberty on Schooner America

  • USA
  • Superb65 reviews4.8

Offering a premium sailing experience, the Schooner America is a tribute to the original America t....

    Free Cancellation
    Private Tour
    Start From $60.08
 
 

Polynesian Canoe Sunset Sail

(4.9 of 126 reviews)

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

Free Cancellation
Private Tour
Start From $250.00
 
Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • USA
  • Superb126 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....

    Free Cancellation
    Private Tour
    Start From $250.00
 
 

Let's Go Sail the York River in Gloucester Point, Virginia

(5 of 148 reviews)

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the cockpit or up on the bow of the boat for greater privacy. Great idea for engagement, bi... More

Free Cancellation
Private Tour
Start From $96.42
 
Let's Go Sail the York River in Gloucester Point, Virginia Likely to Sell Out

Let's Go Sail the York River in Gloucester Point, Virginia

  • USA
  • Superb148 reviews5

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern ....

    Free Cancellation
    Private Tour
    Start From $96.42
 
 

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
 
 

All Inclusive 3 Hours Private Afternoon Sail in Saint Petersburg

(4.9 of 75 reviews)

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks,... More

Free Cancellation
Private Tour
Start From $1,100.00
 
All Inclusive 3 Hours Private Afternoon Sail in Saint Petersburg Likely to Sell Out

All Inclusive 3 Hours Private Afternoon Sail in Saint Petersburg

  • USA
  • Superb75 reviews4.9

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and cr....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
 

Private Half Day Sailing Charter in Portland Maine

(5 of 1 review)

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast... More

Free Cancellation
Private Tour
Start From $475.00
 
Private Half Day Sailing Charter in Portland Maine Likely to Sell Out

Private Half Day Sailing Charter in Portland Maine

  • USA
  • Superb1 review5

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast.....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

NYC Statue of Liberty Tall Ship Sail aboard Clipper City

(4.3 of 266 reviews)

Step aboard the majestic Clipper City and feel the city fade into the background as the wind fills the sails. Glide through New York Harbor in style, with the Brooklyn Bridge, Statue of Liberty, Ellis Island, and the glittering Ma... More

Free Cancellation
Private Tour
Start From $72.60
 
NYC Statue of Liberty Tall Ship Sail aboard Clipper City Likely to Sell Out

NYC Statue of Liberty Tall Ship Sail aboard Clipper City

  • USA
  • Exellent266 reviews4.3

Step aboard the majestic Clipper City and feel the city fade into the background as the wind fills t....

    Free Cancellation
    Private Tour
    Start From $72.60
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.7 of 60 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Private Tour
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui Likely to Sell Out

Hawaiian Canoe Sailing Experience in Maui

  • USA
  • Superb60 reviews4.7

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Diamond Head Sunset Sail

(4.7 of 15 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More

Free Cancellation
Private Tour
Start From $695.00
 
Diamond Head Sunset Sail Likely to Sell Out

Diamond Head Sunset Sail

  • USA
  • Superb15 reviews4.7

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 470 reviews)

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More

Free Cancellation
Private Tour
Start From $108.91
 
Shallow Water Snorkeling and Dolphin Watching in Key West Likely to Sell Out

Shallow Water Snorkeling and Dolphin Watching in Key West

  • USA
  • Superb470 reviews4.6

All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Exciting Public Afternoon Sail in Hilton Head

(4.6 of 470 reviews)

Looking for a more personal sailing experience without booking an entire private charter? The Afternoon Public Sail is the perfect balance. With a maximum of just six guests onboard, you’ll enjoy an intimate, relaxed atmosphere.... More

Free Cancellation
Private Tour
Start From $119.00
 
Exciting Public Afternoon Sail in Hilton Head Likely to Sell Out

Exciting Public Afternoon Sail in Hilton Head

  • USA
  • Superb470 reviews4.6

Looking for a more personal sailing experience without booking an entire private charter? The Aftern....

    Free Cancellation
    Private Tour
    Start From $119.00
 
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