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Top 10 Best North America Sailing Trips

Found 673 Sailing Trips activities in North America. Sort by Popularity. - Page 22
 

2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

(4.7 of 6 reviews)

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More

Free Cancellation
Start From $179.00
 
2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

  • North America
  • Superb6 reviews4.7

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our sta....

    Free Cancellation
    Start From $179.00
 
 

Private Chica SAILING Adventure Puerto Vallarta ALL INCLUSIVE

(4.9 of 41 reviews)

Explore the stunning Bay of Banderas aboard the 41-foot Chica Sailing Adventure. Customize your tour to suit your desires—whether you’re after a romantic sunset cruise, adrenaline-pumping sailing, or a tranquil journey to a se... More

Free Cancellation
Private Tour
Start From $1,437.00
 
 Private Chica SAILING Adventure Puerto Vallarta ALL INCLUSIVE

Private Chica SAILING Adventure Puerto Vallarta ALL INCLUSIVE

  • North America
  • Superb41 reviews4.9

Explore the stunning Bay of Banderas aboard the 41-foot Chica Sailing Adventure. Customize your tour....

    Free Cancellation
    Private Tour
    Start From $1,437.00
 
 

Sunset Cruise on the Scenic & Calming Chesapeake Bay

(4.7 of 11 reviews)

Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way to close out a summer day with beautiful photos of the sunset. You must call 24 hours before your cruise time to see if the minimum... More

Free Cancellation
Private Tour
Start From $123.00
 
Sunset Cruise on the Scenic & Calming Chesapeake Bay Likely to Sell Out

Sunset Cruise on the Scenic & Calming Chesapeake Bay

  • North America
  • Superb11 reviews4.7

Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way t....

    Free Cancellation
    Private Tour
    Start From $123.00
 
 

Catamaran to Isla Mujeres

(4 of 5 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 Good5 reviews4

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
 
 

Discovering Isla Mujeres on a Double Decker Catamaran

(3.8 of 12 reviews)

Start your day with a hotel pickup or directly at the marina, then head out to open sea through the spectacular mangrove channels. The bar opens soon after departure. Snorkel at open sea for 30-45 minutes. In addition to the colo... More

Free Cancellation
Private Tour
Start From $79.00
 
Discovering Isla Mujeres on a Double Decker Catamaran Likely to Sell Out

Discovering Isla Mujeres on a Double Decker Catamaran

  • North America
  • Very Good12 reviews3.8

Start your day with a hotel pickup or directly at the marina, then head out to open sea through the ....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Sunset in Private Sailboat 4 hrs up to 15 pax

(4 of 15 reviews)

Sail around the bay, celebrating your birthday, bachelorette party, anniversary or any other important event. You will receive the best service where you will see the sunset very close during this 4-hour tour... More

Free Cancellation
Private Tour
Start From $3,295.00
 
Sunset in Private Sailboat 4 hrs up to 15 pax Likely to Sell Out

Sunset in Private Sailboat 4 hrs up to 15 pax

  • North America
  • Very Good15 reviews4

Sail around the bay, celebrating your birthday, bachelorette party, anniversary or any other importa....

    Free Cancellation
    Private Tour
    Start From $3,295.00
 
 

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

(4.9 of 19 reviews)

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More

Free Cancellation
Private Tour
Start From $54.95
 
Schooner Applejack Sunset Sail Tour in Boothbay Harbor Likely to Sell Out

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

  • North America
  • Superb19 reviews4.9

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....

    Free Cancellation
    Private Tour
    Start From $54.95
 
 

Catamaran and snorkel in isla mujeres

(3 of 4 reviews)

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

Free Cancellation
Private Tour
Start From $57.00
 
Catamaran and snorkel in isla mujeres Likely to Sell Out

Catamaran and snorkel in isla mujeres

  • North America

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 $57.00
 
 

All Inclusive Tulum: Luxury Yacht 50´ Cranchi, 4hrs

(5 of 27 reviews)

An incredible 4 hours experience in an exclusive yacht, tasting exquisite dishes and enjoying a day just for you and your family. You can visit different exclusive places... More

Free Cancellation
Private Tour
Start From $2,100.00
 
All Inclusive Tulum: Luxury Yacht 50´ Cranchi, 4hrs Likely to Sell Out

All Inclusive Tulum: Luxury Yacht 50´ Cranchi, 4hrs

  • North America
  • Superb27 reviews5

An incredible 4 hours experience in an exclusive yacht, tasting exquisite dishes and enjoying a day ....

    Free Cancellation
    Private Tour
    Start From $2,100.00
 
 

All Inclusive Cozumel: Coast & Relax 4hrs Luxury Yacht

(5 of 23 reviews)

Situated in the azure waters of the Mexican Caribbean, Cozumel stands as a jewel of unparalleled beauty. Recognized as Mexico's largest island, it draws travelers with its captivating charm and natural wonders. Diving enthusiasts ... More

Free Cancellation
Private Tour
Start From $2,100.00
 
All Inclusive Cozumel: Coast & Relax 4hrs Luxury Yacht Likely to Sell Out

All Inclusive Cozumel: Coast & Relax 4hrs Luxury Yacht

  • North America
  • Superb23 reviews5

Situated in the azure waters of the Mexican Caribbean, Cozumel stands as a jewel of unparalleled bea....

    Free Cancellation
    Private Tour
    Start From $2,100.00
 
 

Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos

(3.7 of 75 reviews)

Prepare for a thrilling day trip to Isla Mujeres from Cancun, tailored for nature lovers and fun-seekers with our two exciting options: Option 1: All-Inclusive Adventure We'll take you from your Cancun hotel to two incredible sno... More

Free Cancellation
Private Tour
Start From $59.50
 
Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos Likely to Sell Out

Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos

  • North America
  • Very Good75 reviews3.7

Prepare for a thrilling day trip to Isla Mujeres from Cancun, tailored for nature lovers and fun-see....

    Free Cancellation
    Private Tour
    Start From $59.50
 
 

Key West Sail and Snorkel Day Trip from Fort Lauderdale

(3 of 15 reviews)

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from Fort Lauderdale promises thrilling experiences and breathtaking sights both above and ... More

Free Cancellation
Private Tour
Start From $169.00
 
Key West Sail and Snorkel Day Trip from Fort Lauderdale Likely to Sell Out

Key West Sail and Snorkel Day Trip from Fort Lauderdale

  • North America

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it....

    Free Cancellation
    Private Tour
    Start From $169.00
 
 

Private New Orleans 2-Hour Sail Aboard a Luxury Yacht

(5 of 41 reviews)

Escape the ordinary, just 8 miles from the French Quarter! Relax and leave your cares behind while you explore the lake side of New Orleans on a private 2 hour sail. Hop aboard a 47' luxury Beneteau sailboat called "Roux Stir", na... More

Free Cancellation
Private Tour
Start From $225.00
 
Private New Orleans 2-Hour Sail Aboard a Luxury Yacht Likely to Sell Out

Private New Orleans 2-Hour Sail Aboard a Luxury Yacht

  • North America
  • Superb41 reviews5

Escape the ordinary, just 8 miles from the French Quarter! Relax and leave your cares behind while y....

    Free Cancellation
    Private Tour
    Start From $225.00
 
 

Captain Steve's Sailing Experience on Long Island

(5 of 6 reviews)

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience, you can experience the beauty of the area from a unique perspecti... More

Free Cancellation
Private Tour
Start From $475.00
 
Captain Steve's Sailing Experience on Long Island Likely to Sell Out

Captain Steve's Sailing Experience on Long Island

  • North America
  • Superb6 reviews5

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best ....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

3hr Shared Sailing Adventure

(5 of 8 reviews)

Availablie Daily May-Sep Your sailing experience is a great choice to introduce yourself to the sailing world in a casual, relaxed setting. This trip requires no prior sailing knowledge or experience. You have the option of parti... More

Free Cancellation
Private Tour
Start From $170.10
 
3hr Shared Sailing Adventure Likely to Sell Out

3hr Shared Sailing Adventure

  • North America
  • Superb8 reviews5

Availablie Daily May-Sep Your sailing experience is a great choice to introduce yourself to the sai....

    Free Cancellation
    Private Tour
    Start From $170.10
 
 

Sailing Adventure on Okanagan Lake from Penticton & Naramata BC

(5 of 43 reviews)

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We provide hands on instruction and lots of opportunities to learn or just relax. And it is ... More

Free Cancellation
Private Tour
Start From $177.93
 
Sailing Adventure on Okanagan Lake from Penticton & Naramata BC Likely to Sell Out

Sailing Adventure on Okanagan Lake from Penticton & Naramata BC

  • North America
  • Superb43 reviews5

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....

    Free Cancellation
    Private Tour
    Start From $177.93
 
 

Enjoy The Spanish Galeon with a Romantic Night Dinner in Cancun

(3.8 of 4 reviews)

If you are visiting Cancun or Riviera Maya is time to live the most romantic experience sailing on our Columbus cruise, and live an unforgettable evening with that special someone with a dinner to choose between vegetarian, meat o... More

Free Cancellation
Private Tour
Start From $95.00
 
Enjoy The Spanish Galeon with a Romantic Night Dinner in Cancun Likely to Sell Out

Enjoy The Spanish Galeon with a Romantic Night Dinner in Cancun

  • North America
  • Very Good4 reviews3.8

If you are visiting Cancun or Riviera Maya is time to live the most romantic experience sailing on o....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Enjoying A Beautiful Day With Mother Nature Cruises

(4.8 of 31 reviews)

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay. Powered only by Mother Nature's wind! This cruise sails at 9 am, 12 Noon and 3 pm, Tuesday - Sunday a... More

Free Cancellation
Private Tour
Start From $102.00
 
Enjoying A Beautiful Day With Mother Nature Cruises Likely to Sell Out

Enjoying A Beautiful Day With Mother Nature Cruises

  • North America
  • Superb31 reviews4.8

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides th....

    Free Cancellation
    Private Tour
    Start From $102.00
 
 

Private Sunset Sail for Two

(5 of 6 reviews)

A Romantic Private Sail for Two on the San Diego Bay offers a Beautiful Sunset and Downtown City Skyline.... More

Free Cancellation
Private Tour
Start From $499.00
 
Private Sunset Sail for Two Likely to Sell Out

Private Sunset Sail for Two

  • North America
  • Superb6 reviews5

A Romantic Private Sail for Two on the San Diego Bay offers a Beautiful Sunset and Downtown City Sky....

    Free Cancellation
    Private Tour
    Start From $499.00
 
 

Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar

(4.7 of 3 reviews)

Embark on a 3-hour sailing & snorkeling expedition to Land’s End and Pelican’s Rock. Take your picture at The Arch, one of Cabo’s main landmarks, and get a glimpse of Lover’s Beach and the Sea Lion Colony. Known as the a... More

Free Cancellation
Private Tour
Start From $89.00
 
Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar Likely to Sell Out

Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar

  • North America
  • Superb3 reviews4.7

Embark on a 3-hour sailing & snorkeling expedition to Land’s End and Pelican’s Rock. Take your ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
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