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Top 10 Best North America Sailing Trips

Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 16
 

Windjammer Classic Day Sail from Camden, Maine

(4.8 of 406 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
Start From $59.95
 
Windjammer Classic Day Sail from Camden, Maine

Windjammer Classic Day Sail from Camden, Maine

  • North America
  • Superb406 reviews4.8

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

    Free Cancellation
    Start From $59.95
 
 

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

(4.9 of 229 reviews)

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Parti... More

Free Cancellation
Start From $80.00
 
Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

  • North America
  • Superb229 reviews4.9

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wi....

    Free Cancellation
    Start From $80.00
 
 

Golden Gate Bridge Sailing Tour

(4.8 of 51 reviews)

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views of the San Francisco skyline, Sausalito, Angel Island, Tiburon, and Marin... More

Free Cancellation
Start From $129.00
 
Golden Gate Bridge Sailing Tour Likely to Sell Out

Golden Gate Bridge Sailing Tour

  • North America
  • Superb51 reviews4.8

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail....

    Free Cancellation
    Start From $129.00
 
 

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

(4.9 of 108 reviews)

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel safe sailing with highly trained and bilingual staff in this beautiful freshwater paradise. Our years of experience back us up. Qua... More

Free Cancellation
Private Tour
Start From $250.03
 
Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks Likely to Sell Out

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

  • North America
  • Superb108 reviews4.9

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel s....

    Free Cancellation
    Private Tour
    Start From $250.03
 
 

Dolphin Sightseeing Sail Aboard Daydreams Sailboat

(4.9 of 108 reviews)

Your 90 minute Dolphin Sightseeing Sail on our Daydreams sailboat will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way... More

Free Cancellation
Private Tour
Start From $75.00
 
Dolphin Sightseeing Sail Aboard Daydreams Sailboat Likely to Sell Out

Dolphin Sightseeing Sail Aboard Daydreams Sailboat

  • North America
  • Superb108 reviews4.9

Your 90 minute Dolphin Sightseeing Sail on our Daydreams sailboat will include a scenic trip through....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

Open Bar Boat Tour to Arcos, Animas, and Quimixto

(4.9 of 108 reviews)

This tour combines three of the bay’s most iconic locations in one all-inclusive adventure. Travelers love the balance of snorkeling, beach time, and jungle exploration—plus the comfort of a large double-deck boat with open ba... More

Free Cancellation
Private Tour
Start From $95.36
 
Open Bar Boat Tour to Arcos, Animas, and Quimixto Likely to Sell Out

Open Bar Boat Tour to Arcos, Animas, and Quimixto

  • North America
  • Superb108 reviews4.9

This tour combines three of the bay’s most iconic locations in one all-inclusive adventure. Travel....

    Free Cancellation
    Private Tour
    Start From $95.36
 
 

LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

(5 of 4 reviews)

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and the Captain. Enjoy a stunning 1 hr private romantic night cruise and sea life discovery aboard... More

Free Cancellation
Private Tour
Start From $268.00
 
LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl Likely to Sell Out

LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

  • North America
  • Superb4 reviews5

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht....

    Free Cancellation
    Private Tour
    Start From $268.00
 
 

Aloha Wednesday Sunset Sail - Drinks Included - Lux Catamaran

(5 of 5 reviews)

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha Wednesday Sunset Sail. This midweek escape combines tropical charm with st... More

Free Cancellation
Private Tour
Start From $76.00
 
Aloha Wednesday Sunset Sail - Drinks Included - Lux Catamaran Likely to Sell Out

Aloha Wednesday Sunset Sail - Drinks Included - Lux Catamaran

  • North America
  • Superb5 reviews5

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit....

    Free Cancellation
    Private Tour
    Start From $76.00
 
 

Exclusive Isla Mujeres and Cancun Private Yacht Tour

(4.9 of 34 reviews)

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set the stage for a day of exhilaration and relaxation. Cruise along the mesmerizing Cancun coastlines, dive into vibrant coral reefs du... More

Free Cancellation
Private Tour
Start From $720.00
 
Exclusive Isla Mujeres and Cancun Private Yacht Tour Likely to Sell Out

Exclusive Isla Mujeres and Cancun Private Yacht Tour

  • North America
  • Superb34 reviews4.9

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set th....

    Free Cancellation
    Private Tour
    Start From $720.00
 
 

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos

(3.7 of 11 reviews)

Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Barrier Reef System, the world’s second-largest coral reef. Departing daily at 9:00 a.m. and 2:00 p.m., your journey begins with a... More

Free Cancellation
Private Tour
Start From $129.00
 
Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos Likely to Sell Out

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelo....

  • North America
  • Very Good11 reviews3.7

Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Ba....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Whale Watching Amazing Adventure

(3.7 of 11 reviews)

Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cabos in search of the Cabo’s Whales.” Enjoy listening to the beautiful song of the whales, with the help of our new hydrophones... More

Free Cancellation
Private Tour
Start From $97.00
 
Whale Watching Amazing Adventure Likely to Sell Out

Whale Watching Amazing Adventure

  • North America
  • Very Good11 reviews3.7

Get ready for the adventure of a lifetime as we make our way out onto the waters surrounding Los Cab....

    Free Cancellation
    Private Tour
    Start From $97.00
 
 

Private sailing excursions, nice spacious sailboats.

(4.9 of 27 reviews)

We are a new sailboat tour agency in bacalar ~ are sailboats stand out with ease access, very comfortable, 2 canopy’s to keep you protected from the elements and a 5 star crew. We provide an atmosphere for you to take over and T... More

Free Cancellation
Private Tour
Start From $261.66
 
Private sailing excursions, nice spacious sailboats. Likely to Sell Out

Private sailing excursions, nice spacious sailboats.

  • North America
  • Superb27 reviews4.9

We are a new sailboat tour agency in bacalar ~ are sailboats stand out with ease access, very comfor....

    Free Cancellation
    Private Tour
    Start From $261.66
 
 

Schooner Eastwind Sunset Sail to see the Maine Coastline

(4.7 of 61 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 $59.95
 
Schooner Eastwind Sunset Sail to see the Maine Coastline Likely to Sell Out

Schooner Eastwind Sunset Sail to see the Maine Coastline

  • North America
  • Superb61 reviews4.7

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 $59.95
 
 

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

(4.8 of 41 reviews)

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and family to see all the iconic waterfront sights of Newport and Narraganset... More

Free Cancellation
Private Tour
Start From $57.24
 
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport Likely to Sell Out

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

  • North America
  • Superb41 reviews4.8

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard ....

    Free Cancellation
    Private Tour
    Start From $57.24
 
 

Catamaran to Isla Mujeres

(3.8 of 6 reviews)

Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will snorkel and spend time in the exclusive beach club where you will have a delicious buffet.... More

Free Cancellation
Private Tour
Start From $59.00
 
Catamaran to Isla Mujeres Likely to Sell Out

Catamaran to Isla Mujeres

  • North America
  • Very Good6 reviews3.8

Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will s....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

Paddle at Dawn with visit to Cenotes and Islands

(4.9 of 70 reviews)

Dare to live a new experience! During this activity you will connect with your ecological SELF as you paddle towards sunrise. Enjoy a delicious picnic in a natural environment while you immerse yourself in warm and crystal clear w... More

Free Cancellation
Private Tour
Start From $24.42
 
Paddle at Dawn with visit to Cenotes and Islands Likely to Sell Out

Paddle at Dawn with visit to Cenotes and Islands

  • North America
  • Superb70 reviews4.9

Dare to live a new experience! During this activity you will connect with your ecological SELF as yo....

    Free Cancellation
    Private Tour
    Start From $24.42
 
 

Sunday Mimosa Bar Catamaran Sail with Mini Brunch Bites

(5 of 5 reviews)

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, and set sail for a relaxing and refreshing 2-hour cruise through Charleston’s histor... More

Free Cancellation
Private Tour
Start From $57.00
 
Sunday Mimosa Bar Catamaran Sail with Mini Brunch Bites Likely to Sell Out

Sunday Mimosa Bar Catamaran Sail with Mini Brunch Bites

  • North America
  • Superb5 reviews5

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard ou....

    Free Cancellation
    Private Tour
    Start From $57.00
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(5 of 21 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have complimentary drinks (alcoholic beverages available for adults 21+ with valid ID o... More

Free Cancellation
Private Tour
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • North America
  • Superb21 reviews5

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Free Cancellation
    Private Tour
    Start From $47.50
 
 

Key West all Day Beach Pass from Miami

(5 of 21 reviews)

Meet at Miami Beach on Lincoln Road for a 7am departure and we will take a double decker bus and travel to the most famous Key, Key West. When we arrive at 10:30am you will have time to walk around and enjoy Key West. Make it over... More

Free Cancellation
Private Tour
Start From $169.99
 
Key West all Day Beach Pass from Miami Likely to Sell Out

Key West all Day Beach Pass from Miami

  • North America
  • Superb21 reviews5

Meet at Miami Beach on Lincoln Road for a 7am departure and we will take a double decker bus and tra....

    Free Cancellation
    Private Tour
    Start From $169.99
 
 

Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun

(4 of 4 reviews)

This is the most complete tour to Isla Mujeres on board a Catamaran with all the inclusions to give you a real caribbean experience. Discover Isla Mujeres and it's beautiful beach with us, our team is certified and you will spend... More

Free Cancellation
Private Tour
Start From $20.00
 
Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun Likely to Sell Out

Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun

  • North America
  • Very Good4 reviews4

This is the most complete tour to Isla Mujeres on board a Catamaran with all the inclusions to give ....

    Free Cancellation
    Private Tour
    Start From $20.00
 
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