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Top 10 Best USA Sailing Trips

Found 447 Sailing Trips activities in USA. Sort by Popularity.
 

Miami Millionaires Sightseeing Cruise

(4.3 of 1,999 reviews)

Navigate through the beautiful waters and be captivated by the panoramic views of Miami's skyline, the vibrant Port of Miami, the secluded Fisher Island, and the sun-kissed shores of Miami Beach. Witness the opulent mansions of Mi... More

Free Cancellation
Start From $18.00
 
Miami Millionaires Sightseeing Cruise

Miami Millionaires Sightseeing Cruise

  • USA
  • Exellent1,999 reviews4.3

Navigate through the beautiful waters and be captivated by the panoramic views of Miami's skyline, t....

    Free Cancellation
    Start From $18.00
 
 

Miami: Ultimate Boat Party with Open Bar, DJ & After-Party

(4.3 of 1,999 reviews)

Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience. This 3-hour Miami booze cruise offers a unique nightclub atmosphere on the water, complete with a FREE open bar serving unlimited... More

Free Cancellation
Start From $139.00
 
Miami: Ultimate Boat Party with Open Bar, DJ & After-Party

Miami: Ultimate Boat Party with Open Bar, DJ & After-Party

  • USA
  • Exellent1,999 reviews4.3

Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience.....

    Free Cancellation
    Start From $139.00
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 4,985 reviews)

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes approximately 1 hour of snorkeling at Shell Island, where... More

Free Cancellation
Start From $52.43
 
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....

  • USA
  • Superb4,985 reviews4.9

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboa....

    Free Cancellation
    Start From $52.43
 
 
-10% Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

(4.8 of 331 reviews)

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean and coastline as the sky transforms with vibrant hues of orange, pink and gold. Relax on d... More

Special Offer
Free Cancellation
Start From $98.10
(Saving 10% ) $109.00
 
-10% Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

  • USA
  • Superb331 reviews4.8

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....

    Special Offer
    Free Cancellation
    Start From $98.10
    (Saving 10% ) $109.00
 
 
-inf% San Francisco Bay Cruise

San Francisco Bay Cruise

(4.4 of 407 reviews)

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the city's... More

Special Offer
Free Cancellation
Start From $39.00
(Saving inf% ) $0.00
 
-inf% San Francisco Bay Cruise

San Francisco Bay Cruise

  • USA
  • Exellent407 reviews4.4

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour....

    Special Offer
    Free Cancellation
    Start From $39.00
    (Saving inf% ) $0.00
 
 
-inf% Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

(4.7 of 616 reviews)

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More

Special Offer
Free Cancellation
Start From $56.00
(Saving inf% ) $0.00
 
-inf% Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

  • USA
  • Superb616 reviews4.7

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....

    Special Offer
    Free Cancellation
    Start From $56.00
    (Saving inf% ) $0.00
 
 
-inf% Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

(4.9 of 389 reviews)

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), sea scooters, and more—offeri... More

Special Offer
Free Cancellation
Start From $95.00
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

  • USA
  • Superb389 reviews4.9

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamara....

    Special Offer
    Free Cancellation
    Start From $95.00
    (Saving inf% ) $0.00
 
 
-inf% Classic Tall Ship Cruise in Boston Harbor

Classic Tall Ship Cruise in Boston Harbor

(4.7 of 787 reviews)

Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liberty Star or Fame. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeata... More

Special Offer
Free Cancellation
Start From $39.55
(Saving inf% ) $0.00
 
-inf% Classic Tall Ship Cruise in Boston Harbor

Classic Tall Ship Cruise in Boston Harbor

  • USA
  • Superb787 reviews4.7

Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liber....

    Special Offer
    Free Cancellation
    Start From $39.55
    (Saving inf% ) $0.00
 
 
-inf% Waikiki Sunset Cocktail Sail on the Moana Catamaran

Waikiki Sunset Cocktail Sail on the Moana Catamaran

(4.9 of 2,398 reviews)

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Special Offer
Free Cancellation
Start From $89.99
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cocktail Sail on the Moana Catamaran

Waikiki Sunset Cocktail Sail on the Moana Catamaran

  • USA
  • Superb2,398 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Special Offer
    Free Cancellation
    Start From $89.99
    (Saving inf% ) $0.00
 
 
-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,778 reviews)

Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. Swim alongside Hawaiian green sea turtles and vibrant tropical fis... More

Special Offer
Free Cancellation
Start From $59.99
(Saving inf% ) $0.00
 
-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • USA
  • Superb1,778 reviews4.9

Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour....

    Special Offer
    Free Cancellation
    Start From $59.99
    (Saving inf% ) $0.00
 
 
-inf% 1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

(4.1 of 712 reviews)

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More

Special Offer
Free Cancellation
Start From $70.00
(Saving inf% ) $0.00
 
-inf% 1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

  • USA
  • Exellent712 reviews4.1

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....

    Special Offer
    Free Cancellation
    Start From $70.00
    (Saving inf% ) $0.00
 
 
-inf% 2 Hour Sailing Cruise on Lake Tahoe

2 Hour Sailing Cruise on Lake Tahoe

(4.9 of 1,002 reviews)

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other t... More

Special Offer
Free Cancellation
Start From $149.00
(Saving inf% ) $0.00
 
-inf% 2 Hour Sailing Cruise on Lake Tahoe

2 Hour Sailing Cruise on Lake Tahoe

  • USA
  • Superb1,002 reviews4.9

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....

    Special Offer
    Free Cancellation
    Start From $149.00
    (Saving inf% ) $0.00
 
 
-inf% Waikiki 2 hour Turtle Canyon Snorkeling Adventure

Waikiki 2 hour Turtle Canyon Snorkeling Adventure

(4.7 of 1,509 reviews)

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard the either 55-ft open-style catamaran or 50-ft double-decker power catamaran and ... More

Special Offer
Free Cancellation
Start From $80.71
(Saving inf% ) $0.00
 
-inf% Waikiki 2 hour Turtle Canyon Snorkeling Adventure

Waikiki 2 hour Turtle Canyon Snorkeling Adventure

  • USA
  • Superb1,509 reviews4.7

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cr....

    Special Offer
    Free Cancellation
    Start From $80.71
    (Saving inf% ) $0.00
 
 
-inf% Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

(4.6 of 78 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

Special Offer
Free Cancellation
Start From $141.98
(Saving inf% ) $0.00
 
-inf% Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

  • USA
  • Superb78 reviews4.6

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

    Special Offer
    Free Cancellation
    Start From $141.98
    (Saving inf% ) $0.00
 
 
-inf% Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

(4.7 of 3,834 reviews)

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More

Special Offer
Free Cancellation
Start From $79.00
(Saving inf% ) $0.00
 
-inf% Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

  • USA
  • Superb3,834 reviews4.7

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....

    Special Offer
    Free Cancellation
    Start From $79.00
    (Saving inf% ) $0.00
 
 
-inf% Evening Colors Sunset Sail Tour in Seattle

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 704 reviews)

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut the engine down and enjoy the quiet of our beautiful schooner cutting through the tranquil Puget So... More

Special Offer
Free Cancellation
Start From $65.00
(Saving inf% ) $0.00
 
-inf% Evening Colors Sunset Sail Tour in Seattle

Evening Colors Sunset Sail Tour in Seattle

  • USA
  • Superb704 reviews4.8

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....

    Special Offer
    Free Cancellation
    Start From $65.00
    (Saving inf% ) $0.00
 
 
-inf% City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

(4.5 of 563 reviews)

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, this journey takes you past iconic landmarks such as Seaport Village, Shelter Island, and the ship-building docks. Gaze at the scenic... More

Special Offer
Free Cancellation
Start From $38.33
(Saving inf% ) $0.00
 
-inf% City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

  • USA
  • Exellent563 reviews4.5

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, thi....

    Special Offer
    Free Cancellation
    Start From $38.33
    (Saving inf% ) $0.00
 
 
-inf% Seattle Sailing Harbor Tour

Seattle Sailing Harbor Tour

(4.7 of 564 reviews)

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More

Special Offer
Free Cancellation
Start From $39.00
(Saving inf% ) $0.00
 
-inf% Seattle Sailing Harbor Tour

Seattle Sailing Harbor Tour

  • USA
  • Superb564 reviews4.7

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....

    Special Offer
    Free Cancellation
    Start From $39.00
    (Saving inf% ) $0.00
 
 
-inf% Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 805 reviews)

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More

Special Offer
Free Cancellation
Start From $56.00
(Saving inf% ) $0.00
 
-inf% Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....

  • USA
  • Exellent805 reviews4.5

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....

    Special Offer
    Free Cancellation
    Start From $56.00
    (Saving inf% ) $0.00
 
 
-inf% Key West Reef Morning Snorkeling with Breakfast and Mimosas

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(4.5 of 728 reviews)

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Special Offer
Free Cancellation
Start From $53.70
(Saving inf% ) $0.00
 
-inf% Key West Reef Morning Snorkeling with Breakfast and Mimosas

Key West Reef Morning Snorkeling with Breakfast and Mimosas

  • USA
  • Exellent728 reviews4.5

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....

    Special Offer
    Free Cancellation
    Start From $53.70
    (Saving inf% ) $0.00
 
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