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Top 10 Best North America Sailing Trips

Found 673 Sailing Trips activities in North America. Sort by Popularity. - Page 14
 

Sail Splash and Sailing Excursion in Ft. Lauderdale

(4.8 of 261 reviews)

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran, the Spirit of Lauderdale. Enjoy one of the best cruise Ft Lauderdale has to offer . Sit back... More

Free Cancellation
Start From $89.00
 
Sail Splash and Sailing Excursion in Ft. Lauderdale

Sail Splash and Sailing Excursion in Ft. Lauderdale

  • North America
  • Superb261 reviews4.8

Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....

    Free Cancellation
    Start From $89.00
 
 

Sunset Luxury Sail on Tampa Bay

(5 of 8 reviews)

Set sail aboard Hawkeye, a brand-new 47-foot luxury sailboat made locally by Island Packet Yachts. Cruise along Downtown St. Petersburg’s scenic waterfront and watch the city glisten in the setting sun. This is a luxury, two-ho... More

Free Cancellation
Start From $125.00
 
Sunset Luxury Sail on Tampa Bay Likely to Sell Out

Sunset Luxury Sail on Tampa Bay

  • North America
  • Superb8 reviews5

Set sail aboard Hawkeye, a brand-new 47-foot luxury sailboat made locally by Island Packet Yachts. C....

    Free Cancellation
    Start From $125.00
 
 

Sea to Sky Afternoon Sail

(5 of 198 reviews)

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds with the breathtaking views of the Coastal and Tantalus mountain ranges. We will depart from the docks in Squamish (about 40 minut... More

Free Cancellation
Start From $127.40
 
Sea to Sky Afternoon Sail Likely to Sell Out

Sea to Sky Afternoon Sail

  • North America
  • Superb198 reviews5

Prepare yourself for an adventure that balances the thrill of sailing Howe Sound's legendary winds w....

    Free Cancellation
    Start From $127.40
 
 

Escape from the Rock! Cruise around Alcatraz

(4.2 of 154 reviews)

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an in-depth view of the prison. Take in the sights and sounds of ... More

Free Cancellation
Start From $46.00
 
Escape from the Rock! Cruise around Alcatraz Likely to Sell Out

Escape from the Rock! Cruise around Alcatraz

  • North America
  • Exellent154 reviews4.2

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and ....

    Free Cancellation
    Start From $46.00
 
 

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

(4.9 of 30 reviews)

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More

Free Cancellation
Start From $119.00
 
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak Likely to Sell Out

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

  • North America
  • Superb30 reviews4.9

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....

    Free Cancellation
    Start From $119.00
 
 

Polynesian Canoe Morning Sail

(5 of 16 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Free Cancellation
Start From $200.00
 
Polynesian Canoe Morning Sail Likely to Sell Out

Polynesian Canoe Morning Sail

  • North America
  • Superb16 reviews5

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Start From $200.00
 
 

Isla Mujeres Sailing Adventure from Riviera Maya

(3.7 of 12 reviews)

Enjoy an amazing sailing journey to Isla Mujeres on a 40ft Fountaine Pajot luxury vessel.
Surrounded by all the scale of blue colors, you'll relax and chill, laying in the shade of the big cockpit  or in a comfortable living r... More

Free Cancellation
Start From $149.00
 
Isla Mujeres Sailing Adventure from Riviera Maya Likely to Sell Out

Isla Mujeres Sailing Adventure from Riviera Maya

  • North America
  • Very Good12 reviews3.7

Enjoy an amazing sailing journey to Isla Mujeres on a 40ft Fountaine Pajot luxury vessel.
Surroun....

    Free Cancellation
    Start From $149.00
 
 

FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry

(3.9 of 9 reviews)

Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the world's best beaches. The ocean crossing is provided with our comfortable Express-Ferry featuring restrooms, comfortable seats, air ... More

Special Offer
Free Cancellation
Start From $284.05
(Saving 5% ) $299.00
 
-5% FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry Likely to Sell Out

FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry

  • North America
  • Very Good9 reviews3.9

Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the wo....

    Special Offer
    Free Cancellation
    Start From $284.05
    (Saving 5% ) $299.00
 
 

Boat & Yacht Tour Amazing Sandbar Adventure, Water Toys & Snorkel

(3.9 of 9 reviews)

Enjoy the day on the water with friends and family with Dolphin Water Sport. Our +650 reviews on Google with a score of 4.9 guarantee our quality. Come aboard our Boat and Yacht to enjoy an incredible Boat Trip in Miami. We'll cr... More

Free Cancellation
Start From $150.00
 
Boat & Yacht Tour Amazing Sandbar Adventure, Water Toys & Snorkel Likely to Sell Out

Boat & Yacht Tour Amazing Sandbar Adventure, Water Toys & Snorkel

  • North America
  • Very Good9 reviews3.9

Enjoy the day on the water with friends and family with Dolphin Water Sport. Our +650 reviews on Goo....

    Free Cancellation
    Start From $150.00
 
 

Private sailing tour of Bacalar Lagoon

(5 of 275 reviews)

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More

Free Cancellation
Private Tour
Start From $205.00
 
Private sailing tour of Bacalar Lagoon Likely to Sell Out

Private sailing tour of Bacalar Lagoon

  • North America
  • Superb275 reviews5

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....

    Free Cancellation
    Private Tour
    Start From $205.00
 
 

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

(5 of 2 reviews)

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More

Free Cancellation
Private Tour
Start From $63.00
 
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms Likely to Sell Out

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

  • North America
  • Superb2 reviews5

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....

    Free Cancellation
    Private Tour
    Start From $63.00
 
 

Private Sailing between Mangroves

(5 of 127 reviews)

Within the activities of this tour, it will be bird watching, sailing in an ecological way without motor. We will swim in the places with the most crystalline water. we will eat exotic local seasonal fruit. With only your group,... More

Free Cancellation
Private Tour
Start From $169.72
 
Private Sailing between Mangroves Likely to Sell Out

Private Sailing between Mangroves

  • North America
  • Superb127 reviews5

Within the activities of this tour, it will be bird watching, sailing in an ecological way without m....

    Free Cancellation
    Private Tour
    Start From $169.72
 
 

Pau Hana Sunset Cocktail Cruise

(4.8 of 48 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More

Free Cancellation
Private Tour
Start From $165.00
 
Pau Hana Sunset Cocktail Cruise Likely to Sell Out

Pau Hana Sunset Cocktail Cruise

  • North America
  • Superb48 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure

(4.5 of 70 reviews)

Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This is the tour for you! Enjoy sailing in one of our Catamarans and we will ensure that you enjoy your afternoon to the maximum. We wi... More

Free Cancellation
Private Tour
Start From $69.99
 
Afternoon Half-Day Catmaran Sailing and Snorkel Adventure Likely to Sell Out

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure

  • North America
  • Exellent70 reviews4.5

Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This ....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

(4.6 of 71 reviews)

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More

Free Cancellation
Private Tour
Start From $54.95
 
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor Likely to Sell Out

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

  • North America
  • Superb71 reviews4.6

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Private Tour
    Start From $54.95
 
 

Amazing Snorkeling Experience + Real Mexican Tacos

(4.8 of 9 reviews)

This is the classic snorkeling experience when you come to Cancun, it is a must tour in your Itinerary. When you do this experience you feel a connection with nature, it is like taking a little bit of Cancun with you back home. Se... More

Free Cancellation
Private Tour
Start From $39.00
 
Amazing Snorkeling Experience + Real Mexican Tacos Likely to Sell Out

Amazing Snorkeling Experience + Real Mexican Tacos

  • North America
  • Superb9 reviews4.8

This is the classic snorkeling experience when you come to Cancun, it is a must tour in your Itinera....

    Free Cancellation
    Private Tour
    Start From $39.00
 
 

Puerto Vallarta Sunset Gourmet Experience

(4.7 of 7 reviews)

This experience blends fine dining, stunning scenery, and exceptional service in a way that few can match. The journey begins with a luxury catamaran cruise, offering panoramic views of Puerto Vallarta’s coastline at sunset. Unl... More

Free Cancellation
Private Tour
Start From $199.00
 
Puerto Vallarta Sunset Gourmet Experience Likely to Sell Out

Puerto Vallarta Sunset Gourmet Experience

  • North America
  • Superb7 reviews4.7

This experience blends fine dining, stunning scenery, and exceptional service in a way that few can ....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

Private 2-Hour Day Sailing Experience

(5 of 40 reviews)

As the first and only sailing tour in Central Florida, Sailing Orlando is committed to sharing the joy of sailing with our community and its visitors. From day sailing to sunset cruises or learning the ropes, our private tours off... More

Free Cancellation
Private Tour
Start From $85.00
 
Private 2-Hour Day Sailing Experience Likely to Sell Out

Private 2-Hour Day Sailing Experience

  • North America
  • Superb40 reviews5

As the first and only sailing tour in Central Florida, Sailing Orlando is committed to sharing the j....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.7 of 334 reviews)

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More

Free Cancellation
Private Tour
Start From $59.95
 
Windjammer Classic Day Sail from Camden, Maine Likely to Sell Out

Windjammer Classic Day Sail from Camden, Maine

  • North America
  • Superb334 reviews4.7

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

New York City Sailboat Day Cruise to the Statue of Liberty

(4.9 of 118 reviews)

Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides a... More

Free Cancellation
Private Tour
Start From $65.72
 
New York City Sailboat Day Cruise to the Statue of Liberty Likely to Sell Out

New York City Sailboat Day Cruise to the Statue of Liberty

  • North America
  • Superb118 reviews4.9

Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted sc....

    Free Cancellation
    Private Tour
    Start From $65.72
 
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