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Top 10 Best USA Sailing Trips

Found 419 Sailing Trips activities in USA. Sort by Popularity. - Page 10
 

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

(4.8 of 14 reviews)

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

Free Cancellation
Private Tour
Start From $1,150.00
 
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

  • USA
  • Superb14 reviews4.8

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,150.00
 
 

Catamaran Sailing Cruise in Monterey

(4.7 of 27 reviews)

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

Free Cancellation
Private Tour
Start From $65.00
 
Catamaran Sailing Cruise in Monterey

Catamaran Sailing Cruise in Monterey

  • USA
  • Superb27 reviews4.7

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Private Key West Sandbar and Paddle by Boat

(4.9 of 34 reviews)

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

Free Cancellation
Private Tour
Start From $600.00
 
Private Key West Sandbar and Paddle by Boat

Private Key West Sandbar and Paddle by Boat

  • USA
  • Superb34 reviews4.9

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Private Sailing Tour through the Ten Thousands Islands

(4.9 of 144 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 $400.00
 
Private Sailing Tour through the Ten Thousands Islands Likely to Sell Out

Private Sailing Tour through the Ten Thousands Islands

  • USA
  • Superb144 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 $400.00
 
 

Luxury Camden Sailing Experience

(5 of 9 reviews)

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Fastest boat in the harbor... More

Free Cancellation
Private Tour
Start From $125.00
 
Luxury Camden Sailing Experience Likely to Sell Out

Luxury Camden Sailing Experience

  • USA
  • Superb9 reviews5

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Let’s do a morning sail on San Francisco Bay (semi private)

(5 of 6 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 $189.00
 
Let’s do a morning sail on San Francisco Bay (semi private) Likely to Sell Out

Let’s do a morning sail on San Francisco Bay (semi private)

  • USA
  • Superb6 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 $189.00
 
 

BYOB Friday Night Fireworks Cruise

(4.3 of 6 reviews)

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

Free Cancellation
Private Tour
Start From $138.95
 
BYOB Friday Night Fireworks Cruise Likely to Sell Out

BYOB Friday Night Fireworks Cruise

  • USA
  • Exellent6 reviews4.3

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Free Cancellation
    Private Tour
    Start From $138.95
 
 

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

(4.8 of 37 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
  • Superb37 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $63.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 78 reviews)

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

Free Cancellation
Private Tour
Start From $99.00
 
Waikiki small group turtle snorkeling & sailing Likely to Sell Out

Waikiki small group turtle snorkeling & sailing

  • USA
  • Superb78 reviews5

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

2 Hours Holo Holo Sunset Cocktail Sail with Open Bar

(3.5 of 2 reviews)

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

Free Cancellation
Private Tour
Start From $136.42
 
2 Hours Holo Holo Sunset Cocktail Sail with Open Bar Likely to Sell Out

2 Hours Holo Holo Sunset Cocktail Sail with Open Bar

  • USA
  • Good2 reviews3.5

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....

    Free Cancellation
    Private Tour
    Start From $136.42
 
 

Casco Bay: Private Afternoon Charter on Heart's Desire

(4 of 1 review)

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

Free Cancellation
Private Tour
Start From $575.00
 
Casco Bay: Private Afternoon Charter on Heart's Desire Likely to Sell Out

Casco Bay: Private Afternoon Charter on Heart's Desire

  • USA
  • Very Good1 review4

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special ....

    Free Cancellation
    Private Tour
    Start From $575.00
 
 

Private Morning Sail, Dolphin and History Tour on Mystique

(5 of 83 reviews)

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

Free Cancellation
Private Tour
Start From $525.00
 
Private Morning Sail, Dolphin and History Tour on Mystique Likely to Sell Out

Private Morning Sail, Dolphin and History Tour on Mystique

  • USA
  • Superb83 reviews5

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

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Waikiki 3pm Tradewind Sail - Open Bar Included

(4.8 of 245 reviews)

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

Free Cancellation
Private Tour
Start From $53.36
 
Waikiki 3pm Tradewind Sail - Open Bar Included Likely to Sell Out

Waikiki 3pm Tradewind Sail - Open Bar Included

  • USA
  • Superb245 reviews4.8

Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise ....

    Free Cancellation
    Private Tour
    Start From $53.36
 
 

Friday Night Firework Cruise in Waikiki

(4.7 of 23 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
  • Superb23 reviews4.7

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
 
 

Sunset Sail Cruise in Key West

(4.9 of 243 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
  • Superb243 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
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(5 of 17 reviews)

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

Free Cancellation
Private Tour
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • USA
  • Superb17 reviews5

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Free Cancellation
    Private Tour
    Start From $47.50
 
 

Schooner Clearwater- Sailing Cruise-Clearwater Beach

(4.9 of 217 reviews)

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

Free Cancellation
Private Tour
Start From $85.00
 
Schooner Clearwater- Sailing Cruise-Clearwater Beach Likely to Sell Out

Schooner Clearwater- Sailing Cruise-Clearwater Beach

  • USA
  • Superb217 reviews4.9

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wi....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

Private 2-Hour Sunset Sailing Tour on Lake Fairview

(5 of 32 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $84.15
(Saving 15% ) $99.00
 
-15% Private 2-Hour Sunset Sailing Tour on Lake Fairview Likely to Sell Out

Private 2-Hour Sunset Sailing Tour on Lake Fairview

  • USA
  • Superb32 reviews5

Sunset Sailing Tour in Orlando | The Perfect Date Night Experience! Looking for something differen....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $84.15
    (Saving 15% ) $99.00
 
 

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline

(4.8 of 23 reviews)

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

Free Cancellation
Private Tour
Start From $600.00
 
Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline Likely to Sell Out

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline

  • USA
  • Superb23 reviews4.8

Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Mia....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

(5 of 41 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 $550.00
 
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique Likely to Sell Out

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

  • USA
  • Superb41 reviews5

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

    Free Cancellation
    Private Tour
    Start From $550.00
 
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