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Top 10 Best USA Sailing Trips

Found 449 Sailing Trips activities in USA. Sort by Popularity. - Page 10
 

America's Cup Evening Sailing Adventure Newport, RI

(4.9 of 28 reviews)

Get on board for the best hands-on sailing experience Newport, RI has to offer. A 2 hour sail around Narragansett Bay passed many iconic sights including New York Yacht Club, Ida Lewis Light, Fort Adams, Eisenhower House, Hammersm... More

Start From $125.00
 
America's Cup Evening Sailing Adventure Newport, RI

America's Cup Evening Sailing Adventure Newport, RI

  • USA
  • Superb28 reviews4.9

Get on board for the best hands-on sailing experience Newport, RI has to offer. A 2 hour sail around....

    Start From $125.00
 
 

Waikiki Friday Night Fireworks Cruise

(4.5 of 31 reviews)

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More

Free Cancellation
Start From $60.00
 
Waikiki Friday Night Fireworks Cruise Likely to Sell Out

Waikiki Friday Night Fireworks Cruise

  • USA
  • Exellent31 reviews4.5

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Free Cancellation
    Start From $60.00
 
 

Private Classic Sailboat Tour in New York City

(5 of 1 review)

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll enjoy stunning views of iconic landmarks like the Statue of Liberty, E... More

Free Cancellation
Private Tour
Start From $700.00
 
Private Classic Sailboat Tour in New York City Likely to Sell Out

Private Classic Sailboat Tour in New York City

  • USA
  • Superb1 review5

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a ....

    Free Cancellation
    Private Tour
    Start From $700.00
 
 

Sunset Cocktail Cruise on our Sailing Catamaran

(4.8 of 63 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Free Cancellation
Private Tour
Start From $165.00
 
Sunset Cocktail Cruise on our Sailing Catamaran Likely to Sell Out

Sunset Cocktail Cruise on our Sailing Catamaran

  • USA
  • Superb63 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

(5 of 1 review)

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 $1,595.00
 
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People Likely to Sell Out

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

  • USA
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $1,595.00
 
 

Sunset Sail Cruise in Key West

(4.9 of 286 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
  • Superb286 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
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 184 reviews)

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More

Free Cancellation
Private Tour
Start From $70.00
 
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans Likely to Sell Out

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

  • USA
  • Superb184 reviews4.9

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

(4.9 of 42 reviews)

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More

Free Cancellation
Private Tour
Start From $59.95
 
Schooner Applejack Sunset Sail Tour in Boothbay Harbor Likely to Sell Out

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

  • USA
  • Superb42 reviews4.9

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu

(4.6 of 1,334 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

Free Cancellation
Private Tour
Start From $53.31
 
Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu Likely to Sell Out

Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu

  • USA
  • Superb1,334 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Free Cancellation
    Private Tour
    Start From $53.31
 
 

Deluxe Day Sail in San Diego

(5 of 72 reviews)

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More

Free Cancellation
Private Tour
Start From $119.00
 
Deluxe Day Sail in San Diego Likely to Sell Out

Deluxe Day Sail in San Diego

  • USA
  • Superb72 reviews5

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Key West: Sunset Sail + Reef Snorkel & Sandbar

(5 of 35 reviews)

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows yo... More

Free Cancellation
Private Tour
Start From $143.05
 
Key West: Sunset Sail + Reef Snorkel & Sandbar Likely to Sell Out

Key West: Sunset Sail + Reef Snorkel & Sandbar

  • USA
  • Superb35 reviews5

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....

    Free Cancellation
    Private Tour
    Start From $143.05
 
 

Sail San Francisco Bay on the Historic Brigantine Matthew Turner

(5 of 2 reviews)

Set sail on the San Francisco Bay aboard the historic brigantine Matthew Turner, the largest sailboat in the area. Experience the beauty of the bay as you glide past iconic landmarks like the Golden Gate Bridge, Alcatraz, and Ange... More

Free Cancellation
Private Tour
Start From $99.00
 
Sail San Francisco Bay on the Historic Brigantine Matthew Turner Likely to Sell Out

Sail San Francisco Bay on the Historic Brigantine Matthew Turner

  • USA
  • Superb2 reviews5

Set sail on the San Francisco Bay aboard the historic brigantine Matthew Turner, the largest sailboa....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 93 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
  • Superb93 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
 
 

Miami Private Boat Tour- Millionaire’s Row and Celebration Cruise

(4.8 of 270 reviews)

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google. Perfect for birthdays, bachelor or bachelorette parties, proposals, annivers... More

Free Cancellation
Private Tour
Start From $150.00
 
Miami Private Boat Tour- Millionaire’s Row and Celebration Cruise Likely to Sell Out

Miami Private Boat Tour- Millionaire’s Row and Celebration Crui....

  • USA
  • Superb270 reviews4.8

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in ....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Fun Boat Rental with Captain in Miami Beach - up to 6 people

(4.9 of 53 reviews)

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straightforward bareboat charter. Now, let's talk logistics. The captain's compensation is a separate matter, settled directly at the ... More

Free Cancellation
Private Tour
Start From $260.00
 
Fun Boat Rental with Captain in Miami Beach - up to 6 people Likely to Sell Out

Fun Boat Rental with Captain in Miami Beach - up to 6 people

  • USA
  • Superb53 reviews4.9

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straig....

    Free Cancellation
    Private Tour
    Start From $260.00
 
 

Private Sailing Tour through the Ten Thousands Islands

(4.9 of 155 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 $450.00
 
Private Sailing Tour through the Ten Thousands Islands Likely to Sell Out

Private Sailing Tour through the Ten Thousands Islands

  • USA
  • Superb155 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 $450.00
 
 

Private Sunset Catamaran Sail in Cocoa Beach

(4.9 of 155 reviews)

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the bea... More

Free Cancellation
Private Tour
Start From $337.87
 
Private Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Private Sunset Catamaran Sail in Cocoa Beach

  • USA
  • Superb155 reviews4.9

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a....

    Free Cancellation
    Private Tour
    Start From $337.87
 
 

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

(5 of 2 reviews)

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and sail is the perfect combination of warm sun, refreshing salty water, and b... More

Free Cancellation
Private Tour
Start From $70.00
 
2 Hour Swim, Snorkel & Sail (Kewalo Harbor) Likely to Sell Out

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

  • USA
  • Superb2 reviews5

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolph....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

2 hour Catamaran Sailing Cruise on Lake Tahoe

(5 of 2 reviews)

Enjoy the stunning views of Lake Tahoe on a two-hour sailing cruise aboard the 50-foot catamaran, "Blue Zephyr". Perfect for couples, families, or groups, this adventure promises a memorable experience on the water. Relax and take... More

Free Cancellation
Private Tour
Start From $130.00
 
2 hour Catamaran Sailing Cruise on Lake Tahoe Likely to Sell Out

2 hour Catamaran Sailing Cruise on Lake Tahoe

  • USA
  • Superb2 reviews5

Enjoy the stunning views of Lake Tahoe on a two-hour sailing cruise aboard the 50-foot catamaran, "B....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

(4.8 of 251 reviews)

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Sail toward Diamond Head on the famous Waikiki ... More

Free Cancellation
Private Tour
Start From $53.36
 
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value Likely to Sell Out

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

  • USA
  • Superb251 reviews4.8

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sai....

    Free Cancellation
    Private Tour
    Start From $53.36
 
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