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Top 10 Best USA Sailing Trips

Found 426 Sailing Trips activities in USA. Sort by Popularity.
 

Miami Millionaires Sightseeing Cruise

(4.3 of 2,057 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
  • Exellent2,057 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
 
 

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

(4.9 of 574 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

Free Cancellation
Start From $90.00
 
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

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

  • USA
  • Superb574 reviews4.9

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

    Free Cancellation
    Start From $90.00
 
 

San Francisco Bay Cruise

(4.4 of 427 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 Likely to Sell Out

San Francisco Bay Cruise

  • USA
  • Exellent427 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
 
 

Kona Signature Catamaran Sunset Sail

(4.8 of 374 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 Likely to Sell Out

Kona Signature Catamaran Sunset Sail

  • USA
  • Superb374 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
 
 

Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers

(4.9 of 46 reviews)

Experience a romantic Maui sunset together aboard Akialoa, a luxury 55-foot sailing catamaran. This two-hour evening sail takes you into the picturesque ʻAuʻau Channel, where you can unwind together as the sun sets over the Paci... More

Free Cancellation
Start From $126.82
 
Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers Likely to Sell Out

Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers

  • USA
  • Superb46 reviews4.9

Experience a romantic Maui sunset together aboard Akialoa, a luxury 55-foot sailing catamaran. This ....

    Free Cancellation
    Start From $126.82
 
 

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

(4.5 of 418 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 $77.40
 
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
  • Exellent418 reviews4.5

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

    Free Cancellation
    Start From $77.40
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 172 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 $169.00
 
Turtles & Tacos Luxury Catamaran Snorkel Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel

  • USA
  • Superb172 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 $169.00
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 5,059 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 Likely to Sell Out

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

  • USA
  • Superb5,059 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
 
 

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

(4.7 of 1,615 reviews)

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More

Free Cancellation
Start From $222.86
 
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady Likely to Sell Out

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

  • USA
  • Superb1,615 reviews4.7

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....

    Free Cancellation
    Start From $222.86
 
 

Waikiki Sunset Cocktail Sail on the Moana Catamaran

(4.9 of 2,453 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

Free Cancellation
Start From $89.99
 
Waikiki Sunset Cocktail Sail on the Moana Catamaran Likely to Sell Out

Waikiki Sunset Cocktail Sail on the Moana Catamaran

  • USA
  • Superb2,453 reviews4.9

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

    Free Cancellation
    Start From $89.99
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,812 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 $49.99
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • USA
  • Superb1,812 reviews4.9

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

    Free Cancellation
    Start From $49.99
 
 

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

(4.7 of 3,872 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 $75.20
 
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
  • Superb3,872 reviews4.7

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

    Free Cancellation
    Start From $75.20
 
 

Waikiki Sunset Cruise: 2-Hour Catamaran & Swim Adventure in Oahu

(4.7 of 625 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 $58.64
 
Waikiki Sunset Cruise: 2-Hour Catamaran & Swim Adventure in Oahu Likely to Sell Out

Waikiki Sunset Cruise: 2-Hour Catamaran & Swim Adventure in Oahu

  • USA
  • Superb625 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 $58.64
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 739 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 $65.22
 
Evening Colors Sunset Sail Tour in Seattle Likely to Sell Out

Evening Colors Sunset Sail Tour in Seattle

  • USA
  • Superb739 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 $65.22
 
 

Waikiki Sunset Boat Cruise

(4.9 of 264 reviews)

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

Free Cancellation
Start From $51.33
 
Waikiki Sunset Boat Cruise Likely to Sell Out

Waikiki Sunset Boat Cruise

  • USA
  • Superb264 reviews4.9

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....

    Free Cancellation
    Start From $51.33
 
 

Snorkel Sail Adventure off Ka'anapali Beach in Maui

(5 of 53 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 $193.17
 
Snorkel Sail Adventure off Ka'anapali Beach in Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach in Maui

  • USA
  • Superb53 reviews5

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

    Free Cancellation
    Start From $193.17
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 844 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
  • Exellent844 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
 
 

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(4.5 of 742 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 $53.70
 
Key West Reef Morning Snorkeling with Breakfast and Mimosas Likely to Sell Out

Key West Reef Morning Snorkeling with Breakfast and Mimosas

  • USA
  • Exellent742 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 $53.70
 
 

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

(4.5 of 578 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

Free Cancellation
Start From $38.33
 
City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour Likely to Sell Out

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

  • USA
  • Exellent578 reviews4.5

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

    Free Cancellation
    Start From $38.33
 
 

Monterey Bay Whale Watching

(4.6 of 395 reviews)

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More

Free Cancellation
Start From $69.95
 
Monterey Bay Whale Watching Likely to Sell Out

Monterey Bay Whale Watching

  • USA
  • Superb395 reviews4.6

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....

    Free Cancellation
    Start From $69.95
 
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