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Top 10 Best USA Sailing Trips

Found 426 Sailing Trips activities in USA. Sort by Popularity. - Page 20
 

2 Hour Chesapeake Day Sail on Catamaran Epiphany

(5 of 21 reviews)

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel offers cushioned seating and panoramic views of the Chesapeake Bay. Glide... More

Free Cancellation
Start From $245.00
 
2 Hour Chesapeake Day Sail on Catamaran Epiphany

2 Hour Chesapeake Day Sail on Catamaran Epiphany

  • USA
  • Superb21 reviews5

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. ....

    Free Cancellation
    Start From $245.00
 
 

San Diego Private Yacht Charter on a Classic Sailboat

(5 of 4 reviews)

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is a classic 41-ft Friendship sloop skippered by a USCG-licensed captain with 55 years of sailing exp... More

Free Cancellation
Private Tour
Start From $810.00
 
San Diego Private Yacht Charter on a Classic Sailboat

San Diego Private Yacht Charter on a Classic Sailboat

  • USA
  • Superb4 reviews5

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Ph....

    Free Cancellation
    Private Tour
    Start From $810.00
 
 

Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

(3.7 of 3 reviews)

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in the South's picturesque setting, this 2-hour sail gives yo... More

Free Cancellation
Private Tour
Start From $38.00
 
Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

  • USA
  • Very Good3 reviews3.7

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the....

    Free Cancellation
    Private Tour
    Start From $38.00
 
 

Private Long Island Sound Sailing Experience

(3.7 of 3 reviews)

Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled between Great Neck's Kings Point and Port Washington's Sands Point. Oogle at the multi million dollar Mansions lining the coast un... More

Free Cancellation
Private Tour
Start From $650.00
 
Private Long Island Sound Sailing Experience

Private Long Island Sound Sailing Experience

  • USA
  • Very Good3 reviews3.7

Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled ....

    Free Cancellation
    Private Tour
    Start From $650.00
 
 

Kona Coast Luxury Private Yacht Charter

(3.7 of 3 reviews)

Indulge in a personalized sailing experience aboard the luxurious 51-ft Lagoon catamaran, No Wiki. This private charter offers an unforgettable journey along the stunning Kona Coast, where you can snorkel vibrant reefs or simply r... More

Free Cancellation
Private Tour
Start From $1,195.00
 
Kona Coast Luxury Private Yacht Charter

Kona Coast Luxury Private Yacht Charter

  • USA
  • Very Good3 reviews3.7

Indulge in a personalized sailing experience aboard the luxurious 51-ft Lagoon catamaran, No Wiki. T....

    Free Cancellation
    Private Tour
    Start From $1,195.00
 
 

3-Night Private Charter in Lake Clark National Park

(5 of 1 review)

Spend three nights and four days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group of up to six guests. Settle into three queen guest cabins, each with... More

Free Cancellation
Private Tour
Start From $20,512.83
 
3-Night Private Charter in Lake Clark National Park

3-Night Private Charter in Lake Clark National Park

  • USA
  • Superb1 review5

Spend three nights and four days exploring Lake Clark National Park aboard Odyssey, our 50-foot sail....

    Free Cancellation
    Private Tour
    Start From $20,512.83
 
 

6-Night Private Charter in Lake Clark National Park

(5 of 1 review)

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group of up to six guests. Settle into three queen guest cabins, each with ... More

Free Cancellation
Private Tour
Start From $30,769.24
 
6-Night Private Charter in Lake Clark National Park

6-Night Private Charter in Lake Clark National Park

  • USA
  • Superb1 review5

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot saili....

    Free Cancellation
    Private Tour
    Start From $30,769.24
 
 

Private Charter Day Sail For up to 6 People

(5 of 7 reviews)

Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you will get a private sailing trip for up to 6 people on the beautiful classic sailboat Wenonah. An hour and a half harbor day sail is t... More

Free Cancellation
Private Tour
Start From $225.00
 
Private Charter Day Sail For up to 6 People

Private Charter Day Sail For up to 6 People

  • USA
  • Superb7 reviews5

Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you wil....

    Free Cancellation
    Private Tour
    Start From $225.00
 
 

Intimate 2 Hour Sunset Public Sail on the newest sailboat

(5 of 1 review)

Looking for an intimate sunset sailing experience without booking an entire private charter? Your 2-Hour Sunset Public Sail offers the perfect balance. With a maximum of just six guests onboard, you’ll enjoy a peaceful, uncrowde... More

Free Cancellation
Private Tour
Start From $166.67
 
Intimate 2 Hour Sunset Public Sail on the newest sailboat

Intimate 2 Hour Sunset Public Sail on the newest sailboat

  • USA
  • Superb1 review5

Looking for an intimate sunset sailing experience without booking an entire private charter? Your 2-....

    Free Cancellation
    Private Tour
    Start From $166.67
 
 

Oyster Bay Three Hour Sailing Experience

(5 of 1 review)

Set sail on Long Island's Gold Coast with a private 3-hour sailing charter for up to 6 guests aboard WINDSWEPT, a Jeanneau 36i. This charter offers flexible departure times, allowing you to choose a start time that suits your sche... More

Free Cancellation
Private Tour
Start From $825.00
 
Oyster Bay Three Hour Sailing Experience

Oyster Bay Three Hour Sailing Experience

  • USA
  • Superb1 review5

Set sail on Long Island's Gold Coast with a private 3-hour sailing charter for up to 6 guests aboard....

    Free Cancellation
    Private Tour
    Start From $825.00
 
 

Private Afternoon Snorkel with Sunset Sail in Key West

(5 of 4 reviews)

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More

Free Cancellation
Private Tour
Start From $995.00
 
Private Afternoon Snorkel with Sunset Sail in Key West

Private Afternoon Snorkel with Sunset Sail in Key West

  • USA
  • Superb4 reviews5

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that sp....

    Free Cancellation
    Private Tour
    Start From $995.00
 
 

Afternoon Sailboat Cruise on Winyah Bay

(5 of 4 reviews)

Set sail on a serene afternoon cruise across the stunning Winyah Bay. This 3.5 hour experience is perfect for families, friends, or small celebrations, allowing you to soak in the coastal breezes and picturesque views of the Lowco... More

Free Cancellation
Private Tour
Start From $145.00
 
Afternoon Sailboat Cruise on Winyah Bay

Afternoon Sailboat Cruise on Winyah Bay

  • USA
  • Superb4 reviews5

Set sail on a serene afternoon cruise across the stunning Winyah Bay. This 3.5 hour experience is pe....

    Free Cancellation
    Private Tour
    Start From $145.00
 
 

All Inclusive Half Day Sunset Catamaran Adventure

(5 of 1 review)

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 $2,000.00
 
All Inclusive Half Day Sunset Catamaran Adventure

All Inclusive Half Day Sunset Catamaran Adventure

  • USA
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $2,000.00
 
 

Private Dolphin Sightseeing Sail on the Lazy Daze Catamaran

(5 of 1 review)

Join us for a Private Charter aboard the 41-foot catamaran Lazy Daze and experience fun dolphin sightseeing as we sail in the shimmering waters of the Gulf of Mexico. This private charter can accommodate a maximum of 32 guests. Th... More

Free Cancellation
Private Tour
Start From $857.00
 
Private Dolphin Sightseeing Sail on the Lazy Daze Catamaran

Private Dolphin Sightseeing Sail on the Lazy Daze Catamaran

  • USA
  • Superb1 review5

Join us for a Private Charter aboard the 41-foot catamaran Lazy Daze and experience fun dolphin sigh....

    Free Cancellation
    Private Tour
    Start From $857.00
 
 

Private Sailing Charters on La Vie Dansante

(5 of 2 reviews)

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht "La Vie Dansante" through Florida’s stunning Intracoastal Waterway.... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Sailing Charters on La Vie Dansante

Private Sailing Charters on La Vie Dansante

  • USA
  • Superb2 reviews5

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your fa....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Private Couples Sunset Sailing Tour in San Diego

(5 of 2 reviews)

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Your sunset saili... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Couples Sunset Sailing Tour in San Diego

Private Couples Sunset Sailing Tour in San Diego

  • USA
  • Superb2 reviews5

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Private Dolphin Catamaran Sail In Cocoa Beach

(5 of 2 reviews)

Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter playful dolph... More

Free Cancellation
Private Tour
Start From $337.87
 
Private Dolphin Catamaran Sail In Cocoa Beach

Private Dolphin Catamaran Sail In Cocoa Beach

  • USA
  • Superb2 reviews5

Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforg....

    Free Cancellation
    Private Tour
    Start From $337.87
 
 

Glass Bottom Boat Fireworks and After Dark Reef Walker Cruise

(5 of 2 reviews)

Waikiki transforms into a vibrant spectacle on Friday nights, and the Friday Fireworks Cruise offers a unique vantage point to experience this magic. Departing from Kewalo Basin, enjoy a 90-minute cruise with stunning views of the... More

Free Cancellation
Private Tour
Start From $89.00
 
Glass Bottom Boat Fireworks and After Dark Reef Walker Cruise

Glass Bottom Boat Fireworks and After Dark Reef Walker Cruise

  • USA
  • Superb2 reviews5

Waikiki transforms into a vibrant spectacle on Friday nights, and the Friday Fireworks Cruise offers....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Private Charter: Shell Island Snorkeling & Dolphin Adventure

(4.8 of 32 reviews)

What makes this experience truly special is that it is a private charter designed entirely around your group. Unlike crowded tours with fixed schedules, this trip offers a relaxed and flexible experience where the day can be tailo... More

Free Cancellation
Private Tour
Start From $640.93
 
Private Charter: Shell Island Snorkeling & Dolphin Adventure

Private Charter: Shell Island Snorkeling & Dolphin Adventure

  • USA
  • Superb32 reviews4.8

What makes this experience truly special is that it is a private charter designed entirely around yo....

    Free Cancellation
    Private Tour
    Start From $640.93
 
 

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

(5 of 1 review)

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea l... More

Free Cancellation
Private Tour
Start From $800.00
 
Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

  • USA
  • Superb1 review5

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking....

    Free Cancellation
    Private Tour
    Start From $800.00
 
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