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Top 10 Best North America Sailing Trips

Found 671 Sailing Trips activities in North America. Sort by Popularity. - Page 30
 

Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers

(5 of 12 reviews)

Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you explore stunning sites and Caribbean reefs. Experience the magic of the Mexican Caribbean, snorkeling in Isla Mujeres and Cancun's ... More

Free Cancellation
Private Tour
Start From $5,900.00
 
Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers

Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 ....

  • North America
  • Superb12 reviews5

Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you e....

    Free Cancellation
    Private Tour
    Start From $5,900.00
 
 

Key West Private Romantic Sunset Sail for Couples

(1 of 1 review)

Cruise the iridescent waters of Florida Keys coast on a romantic 2-hour sailing trip at sunset. Enjoy the intimate atmosphere of this private sailing trip as you admire Florida Keys sparkling skyline at dusk . Allow your expert sk... More

Free Cancellation
Private Tour
Start From $999.00
 
Key West Private Romantic Sunset Sail for Couples

Key West Private Romantic Sunset Sail for Couples

  • North America

Cruise the iridescent waters of Florida Keys coast on a romantic 2-hour sailing trip at sunset. Enjo....

    Free Cancellation
    Private Tour
    Start From $999.00
 
 

Sunset Boat Tour Includes Open Bar and Dinner

(1 of 1 review)

No trip to Cabo is complete with a sunset boat tour of the world famous arch. This is the sunset boat tour that covers all of your bucket list checks! Open bar, light food, a sunset boat tour and memories to last a lifetime!... More

Free Cancellation
Private Tour
Start From $79.00
 
Sunset Boat Tour Includes Open Bar and Dinner

Sunset Boat Tour Includes Open Bar and Dinner

  • North America

No trip to Cabo is complete with a sunset boat tour of the world famous arch. This is the sunset boa....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

3 in 1 Snorkeling, Parasailing, with Meco Ruins Free

(5 of 1 review)

Have a funny and incredible experience full of nature, doing 3 activities at water and land in a tour package! Fly and see the gorgeous views of the Carribean at 260 ft. By the way, you feel free and you liberate adrenaline! ... More

Free Cancellation
Private Tour
Start From $180.00
 
3 in 1 Snorkeling, Parasailing, with Meco Ruins Free

3 in 1 Snorkeling, Parasailing, with Meco Ruins Free

  • North America
  • Superb1 review5

Have a funny and incredible experience full of nature, doing 3 activities at water and land in a tou....

    Free Cancellation
    Private Tour
    Start From $180.00
 
 

2-hour Customizable Private Day Sail in Key West

(1 of 1 review)

This 2-hour, customizable day sail allows for you to experience the pristine Florida Keys water upon one of our historic schooners. This trip has a capacity of up to 26 people, and a selection of sodas, beer, and wine are included... More

Free Cancellation
Private Tour
Start From $2,100.00
 
2-hour Customizable Private Day Sail in Key West

2-hour Customizable Private Day Sail in Key West

  • North America

This 2-hour, customizable day sail allows for you to experience the pristine Florida Keys water upon....

    Free Cancellation
    Private Tour
    Start From $2,100.00
 
 

Private Experience in Punta Mosquito Holbox

(1 of 1 review)

If you come to Holbox you cannot miss a visit to Punta Mosquito, one of the most beautiful beaches on the entire Holbox Island, visit the flamingos and enjoy the beaches, the water and the beautiful sand banks of Punta Mosquito on... More

Free Cancellation
Private Tour
Start From $138.86
 
Private Experience in Punta Mosquito Holbox

Private Experience in Punta Mosquito Holbox

  • North America

If you come to Holbox you cannot miss a visit to Punta Mosquito, one of the most beautiful beaches o....

    Free Cancellation
    Private Tour
    Start From $138.86
 
 

Themed and Special Event Cruise in Chesapeake Bay

(5 of 1 review)

This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and a guest or you and 5 of your best friends will all help you celebrate that birthday, anniversa... More

Free Cancellation
Private Tour
Start From $699.00
 
Themed and Special Event Cruise in Chesapeake Bay Likely to Sell Out

Themed and Special Event Cruise in Chesapeake Bay

  • North America
  • Superb1 review5

This cruise is a unique way to celebrate that special event in your life while cruising on your very....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

Private Sunset Sail in Key West Florida

(5 of 1 review)

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch Key West's Famous sunsets. View Dolphins, Turtles, and all kinds of Marine Life. Take the helm, l... More

Free Cancellation
Private Tour
Start From $750.00
 
Private Sunset Sail in Key West Florida Likely to Sell Out

Private Sunset Sail in Key West Florida

  • North America
  • Superb1 review5

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just ....

    Free Cancellation
    Private Tour
    Start From $750.00
 
 

Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs

(5 of 1 review)

Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting nautical activities! If you are looking to live a unique and unforgettable experience with family or friends, this is the perfect plac... More

Free Cancellation
Private Tour
Start From $3,708.00
 
Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs Likely to Sell Out

Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs

  • North America
  • Superb1 review5

Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting naut....

    Free Cancellation
    Private Tour
    Start From $3,708.00
 
 

All Inclusive Luxury Isla Mujeres Catamaran 51¨Leopard 4hrs

(5 of 2 reviews)

It is a private experience, where you can enjoy the Caribbean Sea while our chef cooks exclusive and delicious dishes and our host will serve you 'refreshing cocktails.... More

Free Cancellation
Private Tour
Start From $3,150.00
 
All Inclusive Luxury Isla Mujeres Catamaran 51¨Leopard 4hrs Likely to Sell Out

All Inclusive Luxury Isla Mujeres Catamaran 51¨Leopard 4hrs

  • North America
  • Superb2 reviews5

It is a private experience, where you can enjoy the Caribbean Sea while our chef cooks exclusive and....

    Free Cancellation
    Private Tour
    Start From $3,150.00
 
 

San Diego Private Morning Sail up to 12 guests

(5 of 30 reviews)

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More

Free Cancellation
Private Tour
Start From $235.00
 
San Diego Private Morning Sail up to 12 guests Likely to Sell Out

San Diego Private Morning Sail up to 12 guests

  • North America
  • Superb30 reviews5

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's w....

    Free Cancellation
    Private Tour
    Start From $235.00
 
 

Sailing Charter

(5 of 30 reviews)

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend out of scenic Sequim Bay! Ingrid Princess is an ocean going, full keel ketch avail... More

Free Cancellation
Private Tour
Start From $165.00
 
Sailing Charter Likely to Sell Out

Sailing Charter

  • North America
  • Superb30 reviews5

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

Aloha Wednesday Sunset Sail - All Drinks Included - Lux Catamaran

(5 of 1 review)

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 - All Drinks Included - Lux Catamaran Likely to Sell Out

Aloha Wednesday Sunset Sail - All Drinks Included - Lux Catamaran

  • North America
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $76.00
 
 

Isla Mujeres in Private Catamaran, Snorkeling North Beach

(5 of 9 reviews)

We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired, as we offer 2 options to our customers. Our trained team is always there to pro... More

Special Offer
Free Cancellation
Private Tour
Start From $748.00
(Saving 5% ) $790.00
 
-5% Isla Mujeres in Private Catamaran, Snorkeling North Beach Likely to Sell Out

Isla Mujeres in Private Catamaran, Snorkeling North Beach

  • North America
  • Superb9 reviews5

We specialize in making this all-day trip unique, a unique and beautiful experience for all our gues....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $748.00
    (Saving 5% ) $790.00
 
 

Private Catamaran Sailboat 4hrs 15Pax

(5 of 9 reviews)

Sail through the bay of Puerto Vallarta celebrating any occasion. A birthday, an engagement, bachelor party or alone enjoy a private sunset with your friends.... More

Free Cancellation
Private Tour
Start From $3,058.00
 
Private Catamaran Sailboat 4hrs 15Pax Likely to Sell Out

Private Catamaran Sailboat 4hrs 15Pax

  • North America
  • Superb9 reviews5

Sail through the bay of Puerto Vallarta celebrating any occasion. A birthday, an engagement, bachelo....

    Free Cancellation
    Private Tour
    Start From $3,058.00
 
 

Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp

(5 of 12 reviews)

Experience the Caribbean like never before with our sophisticated seafarer guiding you through its pristine waters. During this tour, you will have one snorkel stop at any of the following places: El meco, Sac Bajo, El Farito, or... More

Free Cancellation
Private Tour
Start From $4,899.00
 
Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp Likely to Sell Out

Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp

  • North America
  • Superb12 reviews5

Experience the Caribbean like never before with our sophisticated seafarer guiding you through its p....

    Free Cancellation
    Private Tour
    Start From $4,899.00
 
 

Private Yacht for up to 30 People

(5 of 12 reviews)

This ship is a wonderful option to plan unforgettable vacations and spectacular celebrations. With a length of 50 feet, it can accommodate up to 30 guests. Renting the Carver 50 is the perfect option for a variety of events and cr... More

Free Cancellation
Private Tour
Start From $2,225.00
 
Private Yacht for up to 30 People Likely to Sell Out

Private Yacht for up to 30 People

  • North America
  • Superb12 reviews5

This ship is a wonderful option to plan unforgettable vacations and spectacular celebrations. With a....

    Free Cancellation
    Private Tour
    Start From $2,225.00
 
 

Public Schooner Sail in Greenport

(5 of 12 reviews)

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. U... More

Free Cancellation
Private Tour
Start From $130.00
 
Public Schooner Sail in Greenport Likely to Sell Out

Public Schooner Sail in Greenport

  • North America
  • Superb12 reviews5

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands d....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

Shared Experience Glass Bottom Boat to the Arch in Cabo San Lucas

(5 of 12 reviews)

Set sail on our spacious and comfortable 30-foot glass-bottom boats, equipped with onboard mattresses, music, and plenty of room to relax. This is not just a tour—it’s an experience! You’ll explore the most iconic spots of ... More

Free Cancellation
Private Tour
Start From $26.00
 
Shared Experience Glass Bottom Boat to the Arch in Cabo San Lucas Likely to Sell Out

Shared Experience Glass Bottom Boat to the Arch in Cabo San Lucas

  • North America
  • Superb12 reviews5

Set sail on our spacious and comfortable 30-foot glass-bottom boats, equipped with onboard mattresse....

    Free Cancellation
    Private Tour
    Start From $26.00
 
 

It doesn't get better than this all inclusive 95ft luxury yacht

(5 of 12 reviews)

This all inclusive Baller Package isn't for everyone. If you want THE luxury yacht in Cabo this 95ft is THE one. Hot tub, bedrooms, bathrooms, we are talking 95ft baller baby! Contact us directly to make sure we can get you the ex... More

Free Cancellation
Private Tour
Start From $9,999.00
 
It doesn't get better than this all inclusive 95ft luxury yacht Likely to Sell Out

It doesn't get better than this all inclusive 95ft luxury yacht

  • North America
  • Superb12 reviews5

This all inclusive Baller Package isn't for everyone. If you want THE luxury yacht in Cabo this 95ft....

    Free Cancellation
    Private Tour
    Start From $9,999.00
 
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