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Top 10 Best USA Sailing Trips

Found 402 Sailing Trips activities in USA. Sort by Popularity. - Page 8
 

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

(4.7 of 287 reviews)

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a dolphin or two! This is the only charter offering service from downtown St. Petersb... More

Free Cancellation
Start From $66.67
 
4-Hour St. Pete Pier to Egmont Key Experience by Ferry Likely to Sell Out

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

  • USA
  • Superb287 reviews4.7

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....

    Free Cancellation
    Start From $66.67
 
 

2-Hour Private Sailboat Charter in the San Francisco Bay

(4.9 of 19 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
  • Superb19 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 Catamaran Charter in Waikiki (1-6 Guests)

(5 of 16 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
  • Superb16 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
 
 

Sunset Sail on Historic Schooner in Key West

(4.8 of 98 reviews)

Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then Colonel George Patton "When the war is over and if I return, Bea and I will sail around the world!" Step foot on the gorgeous teak... More

Free Cancellation
Private Tour
Start From $109.00
 
Sunset Sail on Historic Schooner in Key West Likely to Sell Out

Sunset Sail on Historic Schooner in Key West

  • USA
  • Superb98 reviews4.8

Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then ....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Sunset Sail Cruise in Key West

(4.9 of 214 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 $91.38
 
Sunset Sail Cruise in Key West Likely to Sell Out

Sunset Sail Cruise in Key West

  • USA
  • Superb214 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 $91.38
 
 

Skagway Trail and Sail

(5 of 3 reviews)

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike Electric Bicycles where you will join us for a self-guided ride to some of Skagway's best sites! You will visit a waterfall, scenic... More

Free Cancellation
Private Tour
Start From $265.00
 
Skagway Trail and Sail Likely to Sell Out

Skagway Trail and Sail

  • USA
  • Superb3 reviews5

This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....

    Free Cancellation
    Private Tour
    Start From $265.00
 
 

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

(5 of 2 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
  • Superb2 reviews5

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

    Free Cancellation
    Private Tour
    Start From $63.00
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.7 of 334 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
  • Superb334 reviews4.7

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 Morning Sailing/Dolphin & History Tours on 43ft Mystique

(5 of 72 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 for over 12 years, our sailing yachts are the highest quality and op... More

Free Cancellation
Private Tour
Start From $399.00
 
Private Morning Sailing/Dolphin & History Tours on 43ft Mystique Likely to Sell Out

Private Morning Sailing/Dolphin & History Tours on 43ft Mystique

  • USA
  • Superb72 reviews5

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

    Free Cancellation
    Private Tour
    Start From $399.00
 
 

Sunset Sail Experience by Catamaran in Waikiki

(5 of 5 reviews)

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More

Free Cancellation
Private Tour
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki Likely to Sell Out

Sunset Sail Experience by Catamaran in Waikiki

  • USA
  • Superb5 reviews5

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....

    Free Cancellation
    Private Tour
    Start From $92.31
 
 

Waikiki Boat Party Cruise with live DJ

(5 of 5 reviews)

Get ready for the ultimate Day Club experience on the water! Departing from Kewalo Basin Harbor, this exclusive 4-hour catamaran party cruise features an open bar with Vodka, Rum, Whiskey, Gin, Tequila, Champagne, Beer, plus Juice... More

Free Cancellation
Private Tour
Start From $149.00
 
Waikiki Boat Party Cruise with live DJ Likely to Sell Out

Waikiki Boat Party Cruise with live DJ

  • USA
  • Superb5 reviews5

Get ready for the ultimate Day Club experience on the water! Departing from Kewalo Basin Harbor, thi....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Private 2-Hour Morning Sail

(5 of 5 reviews)

Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boat? Come sail with me, Captain John. Let me share my passion for sailing with you. I’m a U.S. certified sailing instructor and li... More

Free Cancellation
Private Tour
Start From $695.00
 
Private 2-Hour Morning Sail Likely to Sell Out

Private 2-Hour Morning Sail

  • USA
  • Superb5 reviews5

Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boa....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Friday Night Firework Cruise in Waikiki

(4.8 of 21 reviews)

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More

Free Cancellation
Private Tour
Start From $69.99
 
Friday Night Firework Cruise in Waikiki Likely to Sell Out

Friday Night Firework Cruise in Waikiki

  • USA
  • Superb21 reviews4.8

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.9 of 102 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More

Free Cancellation
Private Tour
Start From $125.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • USA
  • Superb102 reviews4.9

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 269 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Private Tour
Start From $96.30
 
12pm Turtle Canyon Snorkel Adventure Likely to Sell Out

12pm Turtle Canyon Snorkel Adventure

  • USA
  • Superb269 reviews4.8

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Private Tour
    Start From $96.30
 
 

Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan

(5 of 24 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan Likely to Sell Out

Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan

  • USA
  • Superb24 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

Sailing Charters in Wilmington

(5 of 143 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
Private Tour
Start From $89.99
 
Sailing Charters in Wilmington Likely to Sell Out

Sailing Charters in Wilmington

  • USA
  • Superb143 reviews5

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

    Free Cancellation
    Private Tour
    Start From $89.99
 
 

Private Sailing Charter: Up to 24 Passengers

(5 of 1 review)

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco Bay. While our boats are coast guard licensed for 34 passengers, we are limiting... More

Free Cancellation
Private Tour
Start From $1,207.50
 
Private Sailing Charter: Up to 24 Passengers Likely to Sell Out

Private Sailing Charter: Up to 24 Passengers

  • USA
  • Superb1 review5

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a ....

    Free Cancellation
    Private Tour
    Start From $1,207.50
 
 

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

(4.9 of 187 reviews)

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your adventure yo... More

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways Likely to Sell Out

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

  • USA
  • Superb187 reviews4.9

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Newport Sunset Sail on Classic Sailboat

(4.8 of 17 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
  • Superb17 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
 
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