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Top 10 Best North America Sailing Trips

Found 769 Sailing Trips activities in North America. Sort by Popularity. - Page 2
 

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(4.5 of 698 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

Key West Reef Morning Snorkeling with Breakfast and Mimosas

  • North America
  • Exellent698 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
 
 

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

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • North America
  • Superb41 reviews5

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

    Free Cancellation
    Start From $192.17
 
 

Sunset Windjammer Cruise Along the Coast of Portland Maine

(4.7 of 164 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

Sunset Windjammer Cruise Along the Coast of Portland Maine

  • North America
  • Superb164 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
 
 

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(4.7 of 160 reviews)

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Free Cancellation
Start From $49.00
 
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

  • North America
  • Superb160 reviews4.7

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....

    Free Cancellation
    Start From $49.00
 
 

2 Hour Sailing Cruise on Lake Tahoe

(4.9 of 949 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

Free Cancellation
Start From $149.00
 
2 Hour Sailing Cruise on Lake Tahoe

2 Hour Sailing Cruise on Lake Tahoe

  • North America
  • Superb949 reviews4.9

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

    Free Cancellation
    Start From $149.00
 
 

Buccaneer Pirate Cruise in Destin

(4.9 of 132 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

Buccaneer Pirate Cruise in Destin

  • North America
  • Superb132 reviews4.9

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

    Free Cancellation
    Start From $55.00
 
 

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

Turtles & Tacos Luxury Catamaran Snorkel

  • North America
  • 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
 
 

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

(4.1 of 651 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

Free Cancellation
Start From $70.00
 
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
  • Exellent651 reviews4.1

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

    Free Cancellation
    Start From $70.00
 
 

Waikiki Sunset Boat Cruise

(4.9 of 198 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 $50.00
 
Waikiki Sunset Boat Cruise

Waikiki Sunset Boat Cruise

  • North America
  • Superb198 reviews4.9

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

    Free Cancellation
    Start From $50.00
 
 

Waikiki Sunset Cocktail Sail on the Moana Catamaran

(4.9 of 2,362 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

Waikiki Sunset Cocktail Sail on the Moana Catamaran

  • North America
  • Superb2,362 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
 
 

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

(4.7 of 188 reviews)

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More

Free Cancellation
Start From $69.95
 
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine Likely to Sell Out

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

  • North America
  • Superb188 reviews4.7

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....

    Free Cancellation
    Start From $69.95
 
 

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

(5 of 58 reviews)

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based on weather, tides, and ocean conditions. • Explore Lana... More

Free Cancellation
Start From $216.22
 
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar Likely to Sell Out

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

  • North America
  • Superb58 reviews5

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....

    Free Cancellation
    Start From $216.22
 
 

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

(4.7 of 587 reviews)

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Spacious 45-foot catamaran with near 360 degree view -Families welcome: Keiki ra... More

Free Cancellation
Start From $84.77
 
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

  • North America
  • Superb587 reviews4.7

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boardi....

    Free Cancellation
    Start From $84.77
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,748 reviews)

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More

Free Cancellation
Start From $89.56
 
Waikiki Turtle Snorkel and Sail on Hawea Catamaran Likely to Sell Out

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • North America
  • Superb1,748 reviews4.8

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....

    Free Cancellation
    Start From $89.56
 
 

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

(4.5 of 540 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 $37.17
 
City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour Likely to Sell Out

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

  • North America
  • Exellent540 reviews4.5

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

    Free Cancellation
    Start From $37.17
 
 

Monterey Bay Whale Watching

(4.6 of 344 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

  • North America
  • Superb344 reviews4.6

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

    Free Cancellation
    Start From $69.95
 
 

Waikiki Turtle Snorkeling Tour with Free Pickup

(4.8 of 243 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 $95.00
 
Waikiki Turtle Snorkeling Tour with Free Pickup Likely to Sell Out

Waikiki Turtle Snorkeling Tour with Free Pickup

  • North America
  • Superb243 reviews4.8

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

    Free Cancellation
    Start From $95.00
 
 

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 323 reviews)

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More

Special Offer
Free Cancellation
Start From $79.20
(Saving 20% ) $99.00
 
-20% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon Likely to Sell Out

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • North America
  • Superb323 reviews4.8

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....

    Special Offer
    Free Cancellation
    Start From $79.20
    (Saving 20% ) $99.00
 
 

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

(4.7 of 2,127 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Special Offer
Free Cancellation
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed Likely to Sell Out

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

  • North America
  • Superb2,127 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Special Offer
    Free Cancellation
    Start From $99.00
    (Saving inf% ) $0.00
 
 

Newport Afternoon Sightseeing Sail on Classic Sailboat

(4.8 of 166 reviews)

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, including Newport's historic lighthouses and landmarks, bridges, mansions a... More

Special Offer
Free Cancellation
Start From $57.24
(Saving inf% ) $0.00
 
-inf% Newport Afternoon Sightseeing Sail on Classic Sailboat Likely to Sell Out

Newport Afternoon Sightseeing Sail on Classic Sailboat

  • North America
  • Superb166 reviews4.8

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narraga....

    Special Offer
    Free Cancellation
    Start From $57.24
    (Saving inf% ) $0.00
 
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