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Top 10 Best North America Sailing Trips

Found 674 Sailing Trips activities in North America. Sort by Popularity. - Page 34
 

Private Sunset Sail for Two

(5 of 5 reviews)

Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More

Free Cancellation
Private Tour
Start From $462.00
 
Private Sunset Sail for Two

Private Sunset Sail for Two

  • North America
  • Superb5 reviews5

Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....

    Free Cancellation
    Private Tour
    Start From $462.00
 
 

Adult Only - Cabo San Lucas Romantic Sunset Cruise

(3 of 1 review)

Finding the right for you Sunset Cruise experience can be sometimes overwhelming and more in a destination as diverse as Los Cabos. This experience offers the perfect blend of relaxation, not crowded, Adult only, laid-back fun, de... More

Free Cancellation
Private Tour
Start From $199.00
 
Adult Only - Cabo San Lucas Romantic Sunset Cruise Likely to Sell Out

Adult Only - Cabo San Lucas Romantic Sunset Cruise

  • North America

Finding the right for you Sunset Cruise experience can be sometimes overwhelming and more in a desti....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

Public Schooner Sail in Greenport

(3 of 1 review)

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

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
 
 

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
 
 

Private 2-Hour Wind and Wine Sunset Sail in Key West

(4.9 of 81 reviews)

This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There... More

Free Cancellation
Private Tour
Start From $4,000.00
 
Private 2-Hour Wind and Wine Sunset Sail in Key West Likely to Sell Out

Private 2-Hour Wind and Wine Sunset Sail in Key West

  • North America
  • Superb81 reviews4.9

This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from ....

    Free Cancellation
    Private Tour
    Start From $4,000.00
 
 

Private Morning Ceremony Sailing Charter

(4.9 of 81 reviews)

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to accommodate groups wanting to do private charters in the morning to celeb... More

Free Cancellation
Private Tour
Start From $1,000.00
 
Private Morning Ceremony Sailing Charter Likely to Sell Out

Private Morning Ceremony Sailing Charter

  • North America
  • Superb81 reviews4.9

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, an....

    Free Cancellation
    Private Tour
    Start From $1,000.00
 
 

Early Sail with the Whales from Ma'alaea Harbor

(3.3 of 3 reviews)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Private Tour
Start From $91.89
 
Early Sail with the Whales from Ma'alaea Harbor Likely to Sell Out

Early Sail with the Whales from Ma'alaea Harbor

  • North America
  • Good3 reviews3.3

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Private Tour
    Start From $91.89
 
 

Private tour at Sea of Cortés: Sunset tour or Snorkel

(3.3 of 3 reviews)

We kick off our day with the best available transportation service for our clients, featuring brand-new, fully-equipped vehicles for your comfort. Upon arriving at Puerto Los Cabos Marina, our sailboat will be waiting to begin the... More

Free Cancellation
Private Tour
Start From $1,019.00
 
Private tour at Sea of Cortés: Sunset tour or Snorkel Likely to Sell Out

Private tour at Sea of Cortés: Sunset tour or Snorkel

  • North America
  • Good3 reviews3.3

We kick off our day with the best available transportation service for our clients, featuring brand-....

    Free Cancellation
    Private Tour
    Start From $1,019.00
 
 

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
 
 

Tall Ship Sailing Tour in Chicago with Fireworks Display

(5 of 12 reviews)

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely... More

Free Cancellation
Private Tour
Start From $113.73
 
Tall Ship Sailing Tour in Chicago with Fireworks Display Likely to Sell Out

Tall Ship Sailing Tour in Chicago with Fireworks Display

  • North America
  • Superb12 reviews5

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....

    Free Cancellation
    Private Tour
    Start From $113.73
 
 

Private Sailing Adventure in Bacalar

(5 of 12 reviews)

Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We explore mangroves, shoreline and Cenotes. Our guides are knowledgeable about the area, each point we visit comes with a detail ex... More

Free Cancellation
Private Tour
Start From $230.99
 
Private Sailing Adventure in Bacalar Likely to Sell Out

Private Sailing Adventure in Bacalar

  • North America
  • Superb12 reviews5

Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We....

    Free Cancellation
    Private Tour
    Start From $230.99
 
 

Basic Catamaran to Isla Mujeres from Cancun

(5 of 12 reviews)

Oceanix Isla Mujeres Essential Tour, a 6-hour trip full of fun, relaxation and unforgettable moments in the stunning Mexican Caribbean. Designed for those looking for the perfect combination of sailing excitement, unlimited drinks... More

Free Cancellation
Private Tour
Start From $50.00
 
Basic Catamaran to Isla Mujeres from Cancun Likely to Sell Out

Basic Catamaran to Isla Mujeres from Cancun

  • North America
  • Superb12 reviews5

Oceanix Isla Mujeres Essential Tour, a 6-hour trip full of fun, relaxation and unforgettable moments....

    Free Cancellation
    Private Tour
    Start From $50.00
 
 

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

(5 of 12 reviews)

Sail onboard the only historic days sail schooner out of Camden Maine. Surprise was build in Rockport Massachusetts in 1918. We only carry 18 passengers in all cushions seats. Experienced crew will provide information on wild life... More

Free Cancellation
Private Tour
Start From $65.00
 
Day Sails and Sunset tours on Schooner Surprise in Camden Maine Likely to Sell Out

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

  • North America
  • Superb12 reviews5

Sail onboard the only historic days sail schooner out of Camden Maine. Surprise was build in Rockpor....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Sailing Trip to Dia Island - All Inclusive

(5 of 12 reviews)

Our qualified team brings years of experience and a deep passion for the art of sailing. We take immense joy in every moment spent on the open sea, and it is our pleasure to extend that feeling to our valued customers. Relaxation ... More

Free Cancellation
Private Tour
Start From $94.75
 
Sailing Trip to Dia Island - All Inclusive Likely to Sell Out

Sailing Trip to Dia Island - All Inclusive

  • North America
  • Superb12 reviews5

Our qualified team brings years of experience and a deep passion for the art of sailing. We take imm....

    Free Cancellation
    Private Tour
    Start From $94.75
 
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