Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 419 Sailing Trips activities in USA. Sort by Popularity. - Page 102hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
Private Tour

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
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USA
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Superb14 reviews4.8
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Catamaran Sailing Cruise in Monterey
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of t... More
Private Tour

Catamaran Sailing Cruise in Monterey
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USA
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Superb27 reviews4.7
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....
Private Tour
Private Key West Sandbar and Paddle by Boat
Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More
Private Tour

Private Key West Sandbar and Paddle by Boat
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USA
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Superb34 reviews4.9
Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....
Private Tour
Private Sailing Tour through the Ten Thousands Islands
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
Private Tour

Private Sailing Tour through the Ten Thousands Islands
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USA
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Superb144 reviews4.9
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....
Private Tour

Luxury Camden Sailing Experience
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USA
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Superb9 reviews5
Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....
Private Tour
Let’s do a morning sail on San Francisco Bay (semi private)
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

Let’s do a morning sail on San Francisco Bay (semi private)
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USA
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Superb6 reviews5
Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boa....
Private Tour
BYOB Friday Night Fireworks Cruise
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More
Private Tour

BYOB Friday Night Fireworks Cruise
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USA
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Exellent6 reviews4.3
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
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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Superb37 reviews4.8
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....
Private Tour
Waikiki small group turtle snorkeling & sailing
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More
Private Tour

Waikiki small group turtle snorkeling & sailing
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USA
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Superb78 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
Private Tour
2 Hours Holo Holo Sunset Cocktail Sail with Open Bar
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More
Private Tour

2 Hours Holo Holo Sunset Cocktail Sail with Open Bar
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USA
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Good2 reviews3.5
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
Private Tour
Casco Bay: Private Afternoon Charter on Heart's Desire
This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten. Ride aboard Heart's Desire: designed by famed yacht designer - John... More
Private Tour

Casco Bay: Private Afternoon Charter on Heart's Desire
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USA
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Very Good1 review4
This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special ....
Private Tour
Private Morning Sail, Dolphin and History Tour on Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing yachts are the highest quality and operated by two professional ... More
Private Tour

Private Morning Sail, Dolphin and History Tour on Mystique
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USA
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Superb83 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Waikiki 3pm Tradewind Sail - Open Bar Included
Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphin... More
Private Tour

Waikiki 3pm Tradewind Sail - Open Bar Included
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USA
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Superb245 reviews4.8
Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise ....
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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Superb23 reviews4.7
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....
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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Superb243 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Tour
South Shore Open Sail from Kewalo Harbor Including Drinks
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! We are a 49-passenger beautiful yellow and red retired Waikiki Beach catamaran now operating from Kewalo... More
Private Tour

South Shore Open Sail from Kewalo Harbor Including Drinks
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USA
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Superb17 reviews5
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....
Private Tour
Schooner Clearwater- Sailing Cruise-Clearwater Beach
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Parti... More
Private Tour

Schooner Clearwater- Sailing Cruise-Clearwater Beach
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USA
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Superb217 reviews4.9
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wi....
Private Tour

Private 2-Hour Sunset Sailing Tour on Lake Fairview
Sunset Sailing Tour in Orlando | The Perfect Date Night Experience! Looking for something different to do in Orlando besides theme parks? Escape the crowds and experience the hidden beauty of Central Florida with an unforgettabl... More
Free Cancellation
Private Tour
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Private 2-Hour Sunset Sailing Tour on Lake Fairview
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USA
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Superb32 reviews5
Sunset Sailing Tour in Orlando | The Perfect Date Night Experience! Looking for something differen....
Free Cancellation
Private Tour
(Saving 15% )
Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Miami Beach experience. Connect with nature, discover new landscapes, & create lasting memories as you explore the stunning coastline... More
Private Tour

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
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USA
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Superb23 reviews4.8
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Mia....
Private Tour
Private Sunset Sail BYOB 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 Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique
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USA
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Superb41 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour