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Top 10 Best USA Sailing Trips

Found 411 Sailing Trips activities in USA. Sort by Popularity. - Page 7
 

Deluxe Day Sail in San Diego

(5 of 56 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
Start From $119.00
 
Deluxe Day Sail in San Diego Likely to Sell Out

Deluxe Day Sail in San Diego

  • USA
  • Superb56 reviews5

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

    Free Cancellation
    Start From $119.00
 
 

Key West Day Sail on Schooner America 2.0 with 2 Drinks

(4.9 of 189 reviews)

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean... More

Free Cancellation
Start From $73.10
 
Key West Day Sail on Schooner America 2.0 with 2 Drinks Likely to Sell Out

Key West Day Sail on Schooner America 2.0 with 2 Drinks

  • USA
  • Superb189 reviews4.9

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a ....

    Free Cancellation
    Start From $73.10
 
 

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

(4.8 of 82 reviews)

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Free Cancellation
Start From $119.00
 
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
  • Superb82 reviews4.8

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....

    Free Cancellation
    Start From $119.00
 
 

Day Sailing Adventure in the Florida Marine Sanctuary

(5 of 27 reviews)

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailboat rides feature ... More

Free Cancellation
Start From $99.00
 
Day Sailing Adventure in the Florida Marine Sanctuary Likely to Sell Out

Day Sailing Adventure in the Florida Marine Sanctuary

  • USA
  • Superb27 reviews5

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay....

    Free Cancellation
    Start From $99.00
 
 

2.5 hr Sailboat Tour aboard Orion's Child

(5 of 64 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
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
  • Superb64 reviews5

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

    Free Cancellation
    Start From $130.00
 
 

Sailing Charters in Wilmington

(5 of 185 reviews)

After a successful first season I am happy to be here for back to back seasons. Sail in style on the historic Wilmington river walk. Enjoy a personalized Charter experience with up to six guests. Very few sailboats are up for publ... More

Free Cancellation
Start From $89.00
 
Sailing Charters in Wilmington Likely to Sell Out

Sailing Charters in Wilmington

  • USA
  • Superb185 reviews5

After a successful first season I am happy to be here for back to back seasons. Sail in style on the....

    Free Cancellation
    Start From $89.00
 
 

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

(4.7 of 17 reviews)

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More

Free Cancellation
Start From $80.00
 
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu Likely to Sell Out

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

  • USA
  • Superb17 reviews4.7

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....

    Free Cancellation
    Start From $80.00
 
 

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.8 of 211 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Free Cancellation
Start From $200.00
 
Molokini Snorkel and Performance Sail: Mā’alaea Harbor Likely to Sell Out

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • USA
  • Superb211 reviews4.8

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Free Cancellation
    Start From $200.00
 
 

Premium Miami Yacht Tour Experience: Captain, Champagne & Party!

(5 of 4 reviews)

Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never before! Perfect for any special occasion, this VIP experience promises unforgettable memories Adventure Highlights Biscayne Bay ... More

Free Cancellation
Private Tour
Start From $50.00
 
Premium Miami Yacht Tour Experience: Captain, Champagne & Party! Likely to Sell Out

Premium Miami Yacht Tour Experience: Captain, Champagne & Party!

  • USA
  • Superb4 reviews5

Ready for the party of a lifetime? Hop aboard our luxurious yacht in Miami Beach to party like never....

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

Newport Afternoon Sightseeing Sail on Classic Sailboat

(4.8 of 142 reviews)

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, including Newport's historic lighthouses and landmarks, bridges, mansions a... More

Free Cancellation
Private Tour
Start From $57.24
 
Newport Afternoon Sightseeing Sail on Classic Sailboat Likely to Sell Out

Newport Afternoon Sightseeing Sail on Classic Sailboat

  • USA
  • Superb142 reviews4.8

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narraga....

    Free Cancellation
    Private Tour
    Start From $57.24
 
 

Experience Oceanside Sailing with Whales and dolphins!

(5 of 14 reviews)

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the Oceanside harbor. We cater to guests from many of the five star hotels in the area. We serve an up... More

Free Cancellation
Private Tour
Start From $130.00
 
Experience Oceanside Sailing with Whales and dolphins! Likely to Sell Out

Experience Oceanside Sailing with Whales and dolphins!

  • USA
  • Superb14 reviews5

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and mo....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

Nights of Lights Sailboat Tour St Augustine Sailing

(5 of 3 reviews)

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More

Free Cancellation
Private Tour
Start From $774.00
 
Nights of Lights Sailboat Tour St Augustine Sailing Likely to Sell Out

Nights of Lights Sailboat Tour St Augustine Sailing

  • USA
  • Superb3 reviews5

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....

    Free Cancellation
    Private Tour
    Start From $774.00
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.8 of 407 reviews)

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More

Free Cancellation
Private Tour
Start From $59.95
 
Windjammer Classic Day Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Day Sail from Camden, Maine

  • USA
  • Superb407 reviews4.8

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Private Sailing Tour through the Ten Thousands Islands

(4.9 of 145 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 $390.00
 
Private Sailing Tour through the Ten Thousands Islands Likely to Sell Out

Private Sailing Tour through the Ten Thousands Islands

  • USA
  • Superb145 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 $390.00
 
 

San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

(4.9 of 329 reviews)

Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica of a 1904 gaff rigged friendship sloop. She is an elegant sight under sail, featuring; highly finished woodwork, bronze fixtures, a... More

Free Cancellation
Private Tour
Start From $125.00
 
San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included Likely to Sell Out

San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

  • USA
  • Superb329 reviews4.9

Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 8 reviews)

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Sunset Sail in Waikiki Likely to Sell Out

Private Catamaran Sunset Sail in Waikiki

  • USA
  • Superb8 reviews5

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

Sunset Sail Cruise in Key West

(4.9 of 247 reviews)

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Free Cancellation
Private Tour
Start From $95.00
 
Sunset Sail Cruise in Key West Likely to Sell Out

Sunset Sail Cruise in Key West

  • USA
  • Superb247 reviews4.9

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Your Private Miami Yacht Tour with Music and Champagne

(4.6 of 65 reviews)

Leave the city's hustle behind and discover Miami from a fresh perspective. On this unforgettable journey, our luxurious yacht becomes your private oasis on the water. As we navigate the breathtaking waters of Biscayne Bay, you'll... More

Free Cancellation
Private Tour
Start From $300.00
 
Your Private Miami Yacht Tour with Music and Champagne Likely to Sell Out

Your Private Miami Yacht Tour with Music and Champagne

  • USA
  • Superb65 reviews4.6

Leave the city's hustle behind and discover Miami from a fresh perspective. On this unforgettable jo....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting

(4.7 of 56 reviews)

DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +1200 reviews on Google. What you will get: Nature Immersion: Encounter dolphins, turtles, manatees, and more as you explore Miami's waters Ce... More

Special Offer
Free Cancellation
Private Tour
Start From $58.50
(Saving 10% ) $65.00
 
-10% Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting Likely to Sell Out

Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting

  • USA
  • Superb56 reviews4.7

DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +1200 reviews....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $58.50
    (Saving 10% ) $65.00
 
 

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

(4.9 of 12 reviews)

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 to sustainability and having a minimal impact on the environment ! It is a wholesome adventure that will le... More

Free Cancellation
Private Tour
Start From $500.00
 
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay Likely to Sell Out

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

  • USA
  • Superb12 reviews4.9

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We ....

    Free Cancellation
    Private Tour
    Start From $500.00
 
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