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Top 10 Best North America Sailing Trips

Found 769 Sailing Trips activities in North America. Sort by Popularity.
 

Miami Millionaires Sightseeing Cruise

(4.3 of 1,902 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

  • North America
  • Exellent1,902 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 4,849 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....

  • North America
  • Superb4,849 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
 
 

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

(4.7 of 595 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

  • North America
  • Superb595 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
 
 

San Francisco Bay Cruise

(4.4 of 384 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

  • North America
  • Exellent384 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
 
 

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 660 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

  • North America
  • Superb660 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
 
 

Kona Signature Catamaran Sunset Sail

(4.8 of 297 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

  • North America
  • Superb297 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
 
 

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

(4.7 of 1,485 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

  • North America
  • Superb1,485 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
 
 

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

(4.8 of 3,769 reviews)

Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time to hang out in the pristine water and take it easy aboard the sailboat – you can snorkel with tropical fish, stand atop a paddleb... More

Free Cancellation
Start From $112.00
 
Los Cabos Luxury Sailing, Snorkel and Lunch Cruise Likely to Sell Out

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

  • North America
  • Superb3,769 reviews4.8

Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time t....

    Free Cancellation
    Start From $112.00
 
 

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

(4.6 of 3,550 reviews)

Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — with the option to choose between an Adults Only or Family Friendly experience. Snorkel in warm, crystalline waters, then savor a del... More

Free Cancellation
Start From $55.00
 
Isla Mujeres Luxury Sailing: Adults Only or Family Friendly Likely to Sell Out

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

  • North America
  • Superb3,550 reviews4.6

Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — wit....

    Free Cancellation
    Start From $55.00
 
 

Seattle Sailing Harbor Tour

(4.7 of 517 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

  • North America
  • Superb517 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
 
 

Classic Tall Ship Cruise in Boston Harbor

(4.7 of 718 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

  • North America
  • Superb718 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
 
 

Pirate Ship Sunset Dinner and Show in Los Cabos

(4.3 of 745 reviews)

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic sunset cruise with a show that is the joy for children and grown-ups alike. Our pirates, dance, chant, climb the ropes, while you... More

Free Cancellation
Start From $99.00
 
Pirate Ship Sunset Dinner and Show in Los Cabos Likely to Sell Out

Pirate Ship Sunset Dinner and Show in Los Cabos

  • North America
  • Exellent745 reviews4.3

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....

    Free Cancellation
    Start From $99.00
 
 

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

(4.5 of 386 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

  • North America
  • Exellent386 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
 
 

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

(4.6 of 62 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

  • North America
  • Superb62 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
 
 

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

(4.3 of 1,591 reviews)

Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. Enjoy Cozumel's top attractions and most visited reefs in the Caribbean... More

Special Offer
Free Cancellation
Start From $61.75
(Saving 5% ) $65.00
 
-5% Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs Likely to Sell Out

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

  • North America
  • Exellent1,591 reviews4.3

Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Specta....

    Special Offer
    Free Cancellation
    Start From $61.75
    (Saving 5% ) $65.00
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,712 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 $49.99
(Saving inf% ) $0.00
 
-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • North America
  • Superb1,712 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 $49.99
    (Saving inf% ) $0.00
 
 

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

(4.5 of 775 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 Likely to Sell Out

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

  • North America
  • Exellent775 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
 
 

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

(4.7 of 3,787 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 Likely to Sell Out

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

  • North America
  • Superb3,787 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
 
 

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

(4.9 of 2,045 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

Special Offer
Free Cancellation
Start From $52.43
(Saving inf% ) $0.00
 
-inf% Dolphin Sunset Cruise in Panama City Beach on the Likely to Sell Out

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

  • North America
  • Superb2,045 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $52.43
    (Saving inf% ) $0.00
 
 

Cabo Boat Ride to El Arco & Lover’s Beach with Swimming

(4.6 of 481 reviews)

Enjoy the perfect combination of sightseeing and beach time on this Cabo San Lucas boat ride to El Arco and Lover’s Beach. Cruise along the stunning coastline as you pass iconic landmarks like the Arch, Sea Lion Colony, and Peli... More

Special Offer
Free Cancellation
Start From $24.99
(Saving inf% ) $0.00
 
-inf% Cabo Boat Ride to El Arco & Lover’s Beach with Swimming Likely to Sell Out

Cabo Boat Ride to El Arco & Lover’s Beach with Swimming

  • North America
  • Superb481 reviews4.6

Enjoy the perfect combination of sightseeing and beach time on this Cabo San Lucas boat ride to El A....

    Special Offer
    Free Cancellation
    Start From $24.99
    (Saving inf% ) $0.00
 
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