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Top 10 Best USA Sailing Trips

Found 452 Sailing Trips activities in USA. Sort by Popularity. - Page 9
 

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

(4.5 of 65 reviews)

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters... More

Free Cancellation
Start From $34.95
 
Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

  • USA
  • Exellent65 reviews4.5

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Do....

    Free Cancellation
    Start From $34.95
 
 

Tiki Pub Glow Party Cruise (Adults only)

(4.9 of 18 reviews)

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic of the moonlit waters, paired with tunes and laughter. Join us for the most memora... More

Free Cancellation
Start From $79.95
 
Tiki Pub Glow Party Cruise (Adults only)

Tiki Pub Glow Party Cruise (Adults only)

  • USA
  • Superb18 reviews4.9

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, si....

    Free Cancellation
    Start From $79.95
 
 

Private Charleston Harbor Catamaran Sail

(5 of 28 reviews)

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a panoramic view with large sliding glass doors between the saloon and the rear deck space, with... More

Free Cancellation
Private Tour
Start From $950.00
 
Private Charleston Harbor Catamaran Sail

Private Charleston Harbor Catamaran Sail

  • USA
  • Superb28 reviews5

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing cata....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

(4.9 of 52 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on ou... More

Free Cancellation
Private Tour
Start From $89.00
 
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

  • USA
  • Superb52 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Golden Hour Escape: Private Sunset Sail in Coastal Maine

(5 of 21 reviews)

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined to endure. Set sail along Maine's exquisite coastline aboar... More

Free Cancellation
Private Tour
Start From $849.00
 
Golden Hour Escape: Private Sunset Sail in Coastal Maine Likely to Sell Out

Golden Hour Escape: Private Sunset Sail in Coastal Maine

  • USA
  • Superb21 reviews5

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the settin....

    Free Cancellation
    Private Tour
    Start From $849.00
 
 

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

(5 of 42 reviews)

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a relaxing and comfortable journey around lower Manhattan. En... More

Free Cancellation
Private Tour
Start From $350.00
 
Best Private Luxury Daytime Boat Tour in New York City - 1 Hour Likely to Sell Out

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

  • USA
  • Superb42 reviews5

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time....

    Free Cancellation
    Private Tour
    Start From $350.00
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 463 reviews)

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More

Free Cancellation
Private Tour
Start From $129.00
 
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

  • USA
  • Superb463 reviews4.9

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

(5 of 3 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
  • Superb3 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
 
 

Private Sailing Experience along the Southern Maine Coastline

(5 of 1 review)

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of six guests, this exclusive journey allows you to soak in the stunning scenery while learning about the rich history of the area, i... More

Free Cancellation
Private Tour
Start From $747.00
 
Private Sailing Experience along the Southern Maine Coastline Likely to Sell Out

Private Sailing Experience along the Southern Maine Coastline

  • USA
  • Superb1 review5

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of ....

    Free Cancellation
    Private Tour
    Start From $747.00
 
 

The Boat People Cruise Private Harbor Cruises

(5 of 48 reviews)

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an unforgettable evening with contagious laughter and panoramic views of the Newport Bay. Bring your plus one or ... More

Free Cancellation
Private Tour
Start From $100.00
 
The Boat People Cruise Private Harbor Cruises Likely to Sell Out

The Boat People Cruise Private Harbor Cruises

  • USA
  • Superb48 reviews5

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We ....

    Free Cancellation
    Private Tour
    Start From $100.00
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 152 reviews)

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More

Free Cancellation
Private Tour
Start From $99.00
 
Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • USA
  • Superb152 reviews4.9

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Sunset Sail Cruise in Key West

(4.9 of 290 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
  • Superb290 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
 
 

2hr. SUNSET Sailing Experience on San Francisco Bay

(5 of 28 reviews)

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get the full experience of sailing so you'll have an opportunity to tak... More

Free Cancellation
Private Tour
Start From $149.00
 
2hr. SUNSET Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. SUNSET Sailing Experience on San Francisco Bay

  • USA
  • Superb28 reviews5

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sail....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

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
Private Tour
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
    Private Tour
    Start From $60.00
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 322 reviews)

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

Free Cancellation
Private Tour
Start From $148.00
 
4-Hour Fort Lauderdale Sailing Charter Likely to Sell Out

4-Hour Fort Lauderdale Sailing Charter

  • USA
  • Superb322 reviews4.9

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Private Tour
    Start From $148.00
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 188 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
  • Superb188 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 47 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
  • Superb47 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
 
 

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran

(5 of 5 reviews)

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the ... More

Free Cancellation
Private Tour
Start From $40.00
 
Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran Likely to Sell Out

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran

  • USA
  • Superb5 reviews5

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip thro....

    Free Cancellation
    Private Tour
    Start From $40.00
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 128 reviews)

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Free Cancellation
Private Tour
Start From $289.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui Likely to Sell Out

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • USA
  • Superb128 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Free Cancellation
    Private Tour
    Start From $289.00
 
 

All Inclusive St Pete Private Half Day Catamaran Charter

(4.9 of 128 reviews)

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks,... More

Free Cancellation
Private Tour
Start From $1,700.00
 
All Inclusive St Pete Private Half Day Catamaran Charter Likely to Sell Out

All Inclusive St Pete Private Half Day Catamaran Charter

  • USA
  • Superb128 reviews4.9

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and cr....

    Free Cancellation
    Private Tour
    Start From $1,700.00
 
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