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Top 10 Best USA Sailing Trips

Found 452 Sailing Trips activities in USA. Sort by Popularity.
 

Miami Millionaires Sightseeing Cruise

(4.3 of 1,908 reviews)

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmerizing beauty of Biscayne Bay, while getting an exclusive glimpse into the luxurious lifestyle of Miami's elite, with a bilingual com... More

Free Cancellation
Start From $18.00
 
Miami Millionaires Sightseeing Cruise

Miami Millionaires Sightseeing Cruise

  • USA
  • Exellent1,908 reviews4.3

Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....

    Free Cancellation
    Start From $18.00
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 4,855 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
  • Superb4,855 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
 
 

San Francisco Bay Cruise

(4.4 of 387 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

Free Cancellation
Start From $39.00
 
San Francisco Bay Cruise

San Francisco Bay Cruise

  • USA
  • Exellent387 reviews4.4

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

    Free Cancellation
    Start From $39.00
 
 

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

(4.7 of 598 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

Free Cancellation
Start From $56.00
 
Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

  • USA
  • Superb598 reviews4.7

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

    Free Cancellation
    Start From $56.00
 
 

Kona Signature Catamaran Sunset Sail

(4.8 of 298 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

Free Cancellation
Start From $109.00
 
Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

  • USA
  • Superb298 reviews4.8

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

    Free Cancellation
    Start From $109.00
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 662 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

Free Cancellation
Start From $65.00
 
Evening Colors Sunset Sail Tour in Seattle Likely to Sell Out

Evening Colors Sunset Sail Tour in Seattle

  • USA
  • Superb662 reviews4.8

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

    Free Cancellation
    Start From $65.00
 
 

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

(4.7 of 1,486 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 our either 55-ft open-style catamaran or 50-ft double-decker power catamaran and ... More

Free Cancellation
Start From $80.71
 
Waikiki: 2-hour Turtle Canyon Snorkeling Adventure Likely to Sell Out

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

  • USA
  • Superb1,486 reviews4.7

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

    Free Cancellation
    Start From $80.71
 
 

Seattle Sailing Harbor Tour

(4.7 of 523 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

Free Cancellation
Start From $39.00
 
Seattle Sailing Harbor Tour Likely to Sell Out

Seattle Sailing Harbor Tour

  • USA
  • Superb523 reviews4.7

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

    Free Cancellation
    Start From $39.00
 
 

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

(4.6 of 65 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
Start From $141.98
 
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar Likely to Sell Out

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

  • USA
  • Superb65 reviews4.6

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

    Free Cancellation
    Start From $141.98
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,718 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

Free Cancellation
Start From $59.99
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • USA
  • Superb1,718 reviews4.9

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

    Free Cancellation
    Start From $59.99
 
 

Classic Tall Ship Cruise in Boston Harbor

(4.7 of 723 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

Free Cancellation
Start From $39.55
 
Classic Tall Ship Cruise in Boston Harbor Likely to Sell Out

Classic Tall Ship Cruise in Boston Harbor

  • USA
  • Superb723 reviews4.7

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

    Free Cancellation
    Start From $39.55
 
 

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

(4.9 of 2,050 reviews)

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More

Free Cancellation
Start From $52.43
 
Dolphin Sunset Cruise in Panama City Beach on the Likely to Sell Out

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

  • USA
  • Superb2,050 reviews4.9

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....

    Free Cancellation
    Start From $52.43
 
 

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

(4.7 of 3,789 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

Free Cancellation
Start From $79.00
 
Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres Likely to Sell Out

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

  • USA
  • Superb3,789 reviews4.7

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

    Free Cancellation
    Start From $79.00
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(5 of 41 reviews)

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More

Free Cancellation
Start From $192.17
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • USA
  • Superb41 reviews5

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Start From $192.17
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 780 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

Free Cancellation
Start From $56.00
 
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor Likely to Sell Out

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

  • USA
  • Exellent780 reviews4.5

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

    Free Cancellation
    Start From $56.00
 
 

Buccaneer Pirate Cruise in Destin

(4.8 of 134 reviews)

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More

Free Cancellation
Start From $55.00
 
Buccaneer Pirate Cruise in Destin Likely to Sell Out

Buccaneer Pirate Cruise in Destin

  • USA
  • Superb134 reviews4.8

Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....

    Free Cancellation
    Start From $55.00
 
 

Key West Signature Sunset Sail with Live Music, Open Bar & Food

(4.5 of 387 reviews)

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Free Cancellation
Start From $72.00
 
Key West Signature Sunset Sail with Live Music, Open Bar & Food Likely to Sell Out

Key West Signature Sunset Sail with Live Music, Open Bar & Food

  • USA
  • Exellent387 reviews4.5

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....

    Free Cancellation
    Start From $72.00
 
 

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(4.5 of 704 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

Free Cancellation
Start From $49.95
 
Key West Reef Morning Snorkeling with Breakfast and Mimosas Likely to Sell Out

Key West Reef Morning Snorkeling with Breakfast and Mimosas

  • USA
  • Exellent704 reviews4.5

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

    Free Cancellation
    Start From $49.95
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 144 reviews)

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More

Free Cancellation
Start From $199.00
 
Turtles & Tacos Luxury Catamaran Snorkel Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel

  • USA
  • Superb144 reviews4.7

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....

    Free Cancellation
    Start From $199.00
 
 

Sunset Windjammer Cruise Along the Coast of Portland Maine

(4.7 of 165 reviews)

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a narrated tour, bu... More

Free Cancellation
Start From $77.00
 
Sunset Windjammer Cruise Along the Coast of Portland Maine Likely to Sell Out

Sunset Windjammer Cruise Along the Coast of Portland Maine

  • USA
  • Superb165 reviews4.7

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to exper....

    Free Cancellation
    Start From $77.00
 
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