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Top 10 Best North America Sailing Trips

Found 766 Sailing Trips activities in North America. Sort by Popularity.
 

Miami Millionaires Sightseeing Cruise

(4.3 of 1,997 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

  • North America
  • Exellent1,997 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
 
 

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

(4.9 of 4,979 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
  • Superb4,979 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 327 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

  • North America
  • Superb327 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

  • North America
  • 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 614 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

  • North America
  • Superb614 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 377 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

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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

  • North America
  • Superb377 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 786 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

  • North America
  • Superb786 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% Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

(4.8 of 3,821 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

Special Offer
Free Cancellation
Start From $112.00
(Saving inf% ) $0.00
 
-inf% Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

  • North America
  • Superb3,821 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $112.00
    (Saving inf% ) $0.00
 
 
-5% Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

(4.3 of 1,615 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

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

  • North America
  • Exellent1,615 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
 
 
-inf% 2 Hour Sailing Cruise on Lake Tahoe

2 Hour Sailing Cruise on Lake Tahoe

(4.9 of 1,001 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

  • North America
  • Superb1,001 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% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,772 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 $54.99
(Saving inf% ) $0.00
 
-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • North America
  • Superb1,772 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 $54.99
    (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 our 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

  • North America
  • 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% Waikiki Sunset Cocktail Sail on the Moana Catamaran

Waikiki Sunset Cocktail Sail on the Moana Catamaran

(4.9 of 2,396 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

  • North America
  • Superb2,396 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% 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 710 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

  • North America
  • Exellent710 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% 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

  • North America
  • 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% Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

(4.6 of 3,598 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

Special Offer
Free Cancellation
Start From $55.00
(Saving inf% ) $0.00
 
-inf% Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

  • North America
  • Superb3,598 reviews4.6

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

    Special Offer
    Free Cancellation
    Start From $55.00
    (Saving inf% ) $0.00
 
 
-inf% Evening Colors Sunset Sail Tour in Seattle

Evening Colors Sunset Sail Tour in Seattle

(4.8 of 702 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

  • North America
  • Superb702 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

  • North America
  • 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% 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 3,833 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

  • North America
  • Superb3,833 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% 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

  • North America
  • 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
 
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