Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 402 Sailing Trips activities in USA. Sort by Popularity. - Page 84-Hour St. Pete Pier to Egmont Key Experience by Ferry
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

4-Hour St. Pete Pier to Egmont Key Experience by Ferry
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USA
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Superb287 reviews4.7
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....
2-Hour Private Sailboat Charter in the San Francisco Bay
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
Private Tour

2-Hour Private Sailboat Charter in the San Francisco Bay
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USA
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Superb19 reviews4.9
Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Jus....
Private Tour
Private Catamaran Charter in Waikiki (1-6 Guests)
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
Private Tour

Private Catamaran Charter in Waikiki (1-6 Guests)
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USA
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Superb16 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
Private Tour
Sunset Sail on Historic Schooner in Key West
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
Private Tour

Sunset Sail on Historic Schooner in Key West
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USA
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Superb98 reviews4.8
Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then ....
Private Tour
Sunset Sail Cruise in Key West
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
Private Tour

Sunset Sail Cruise in Key West
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USA
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Superb214 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Tour
Skagway Trail and Sail
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
Private Tour

Skagway Trail and Sail
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USA
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Superb3 reviews5
This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....
Private Tour
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
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
Private Tour

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
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USA
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Superb2 reviews5
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....
Private Tour
Windjammer Classic Day Sail from Camden, Maine
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
Private Tour

Windjammer Classic Day Sail from Camden, Maine
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USA
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Superb334 reviews4.7
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....
Private Tour
Private Morning Sailing/Dolphin & History Tours on 43ft Mystique
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
Private Tour

Private Morning Sailing/Dolphin & History Tours on 43ft Mystique
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USA
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Superb72 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Sunset Sail Experience by Catamaran in Waikiki
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
Private Tour

Sunset Sail Experience by Catamaran in Waikiki
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USA
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Superb5 reviews5
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....
Private Tour
Waikiki Boat Party Cruise with live DJ
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
Private Tour

Waikiki Boat Party Cruise with live DJ
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USA
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Superb5 reviews5
Get ready for the ultimate Day Club experience on the water! Departing from Kewalo Basin Harbor, thi....
Private Tour
Private 2-Hour Morning Sail
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
Private Tour

Private 2-Hour Morning Sail
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USA
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Superb5 reviews5
Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boa....
Private Tour
Friday Night Firework Cruise in Waikiki
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
Private Tour

Friday Night Firework Cruise in Waikiki
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USA
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Superb21 reviews4.8
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....
Private Tour
2-Hour Oahu Sunset Catamaran Sail
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
Private Tour

2-Hour Oahu Sunset Catamaran Sail
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USA
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Superb102 reviews4.9
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....
Private Tour
12pm Turtle Canyon Snorkel Adventure
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
Private Tour

12pm Turtle Canyon Snorkel Adventure
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USA
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Superb269 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Private Tour
Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan
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
Private Tour

Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan
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USA
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Superb24 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
Sailing Charters in Wilmington
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
Private Tour

Sailing Charters in Wilmington
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USA
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Superb143 reviews5
After a successful first season I am happy to be here for back to back seasons. Sail in style on the....
Private Tour
Private Sailing Charter: Up to 24 Passengers
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
Private Tour

Private Sailing Charter: Up to 24 Passengers
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USA
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Superb1 review5
Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a ....
Private Tour
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways
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
Private Tour

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways
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USA
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Superb187 reviews4.9
This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....
Private Tour
Newport Sunset Sail on Classic Sailboat
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
Private Tour

Newport Sunset Sail on Classic Sailboat
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USA
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Superb17 reviews4.8
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....
Private Tour