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Top 10 Best North America Sailing Trips

Found 642 Sailing Trips activities in North America. Sort by Popularity. - Page 24
 

Halifax Summer Breeze Sail

(5 of 11 reviews)

This two-hour sail allows you to soak in the sights along the coastline so close to our urban center! Pass by landmarks such as George's Island, Pier 21, Point Pleasant Park, and more. This laid-back sail is designed for you to en... More

Free Cancellation
Start From $74.63
 
Halifax Summer Breeze Sail Likely to Sell Out

Halifax Summer Breeze Sail

  • North America
  • Superb11 reviews5

This two-hour sail allows you to soak in the sights along the coastline so close to our urban center....

    Free Cancellation
    Start From $74.63
 
 

Explore Bacalar Lagoon in privacy and comfort. Ideal for couples and families.

(4.9 of 89 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 $200.62
 
Explore Bacalar Lagoon in privacy and comfort. Ideal for couples and families. Likely to Sell Out

Explore Bacalar Lagoon in privacy and comfort. Ideal for couples ....

  • North America
  • Superb89 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 $200.62
 
 

Puerto Vallarta Sunset Gourmet Experience

(4.7 of 7 reviews)

Sunset Gourmet Experience combines the best of a cruising voyage on board a luxurious yacht and a high-end dining experience under the shade of palm trees in the gorgeous natural setting of our ocean-front venue.... 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

Sunset Gourmet Experience combines the best of a cruising voyage on board a luxurious yacht and a hi....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

Private Sailing Charter and Guided Tour

(5 of 3 reviews)

Our most popular Galveston cruise lets you see the Galveston Channel and the surrounding area including the most popular sights on the northern part of Galveston. These include the Elissa, the Ocean Star museum, Pier 21, the Port ... More

Free Cancellation
Private Tour
Start From $550.00
 
Private Sailing Charter and Guided Tour Likely to Sell Out

Private Sailing Charter and Guided Tour

  • North America
  • Superb3 reviews5

Our most popular Galveston cruise lets you see the Galveston Channel and the surrounding area includ....

    Free Cancellation
    Private Tour
    Start From $550.00
 
 

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

(3.5 of 2 reviews)

Welcome to an incredible adventure, if what you like is getting to know new places and being in contact with nature, then this activity is for you. We will take you to know the second largest coral reef in the world, the first one... More

Free Cancellation
Private Tour
Start From $55.00
 
Guided Tour of Puerto Morelos Reefs with Snorkeling Experience Likely to Sell Out

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

  • North America
  • Good2 reviews3.5

Welcome to an incredible adventure, if what you like is getting to know new places and being in cont....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

1.5-Hour Koa Kai Adventure Whale Watch

(5 of 1 review)

Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful creatures return to Maui every year to birth their young. During this trip, you will get a chance to hear the whale’s unique songs a... More

Free Cancellation
Private Tour
Start From $109.00
 
1.5-Hour Koa Kai Adventure Whale Watch Likely to Sell Out

1.5-Hour Koa Kai Adventure Whale Watch

  • North America
  • Superb1 review5

Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful crea....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Private - Bacalar sailing across the mesmerizing waters

(4.9 of 8 reviews)

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence of colonial history & pirates. We embark upon a sailing boat to navigate our way across the mesmerizing waters of 7 different shad... More

Free Cancellation
Private Tour
Start From $468.00
 
Private - Bacalar sailing across the mesmerizing waters Likely to Sell Out

Private - Bacalar sailing across the mesmerizing waters

  • North America
  • Superb8 reviews4.9

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence o....

    Free Cancellation
    Private Tour
    Start From $468.00
 
 

Private Key West Sunset Sail

(4.7 of 46 reviews)

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for t... More

Free Cancellation
Private Tour
Start From $595.00
 
Private Key West Sunset Sail Likely to Sell Out

Private Key West Sunset Sail

  • North America
  • Superb46 reviews4.7

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, ....

    Free Cancellation
    Private Tour
    Start From $595.00
 
 

Tour to the Arch of Cabo San Lucas in a transparent glass boat

(3 of 1 review)

The end of the earth, the impressive union of two seas, the Sea of Cortez and the Pacific Sea, an incredible walk to the Arch of Cabo San Lucas where you can see the colony of sea lions and the wonderful rock formations, great att... More

Free Cancellation
Private Tour
Start From $60.00
 
Tour to the Arch of Cabo San Lucas in a transparent glass boat Likely to Sell Out

Tour to the Arch of Cabo San Lucas in a transparent glass boat

  • North America

The end of the earth, the impressive union of two seas, the Sea of Cortez and the Pacific Sea, an in....

    Free Cancellation
    Private Tour
    Start From $60.00
 
 

3 Hours Private Sailboat Ride with Captain

(5 of 1 review)

Private- Three Hour Sailing Excursion with Coast Guard Licensed Captain for up to 6 passengers. We leave from Rainbow Harbor Long Beach and out into the Pacific Ocean in search of sea life such as Sea Birds, California Sea Lions, ... More

Free Cancellation
Private Tour
Start From $475.00
 
3 Hours Private Sailboat Ride with Captain Likely to Sell Out

3 Hours Private Sailboat Ride with Captain

  • North America
  • Superb1 review5

Private- Three Hour Sailing Excursion with Coast Guard Licensed Captain for up to 6 passengers. We l....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

2 Hour Sailing Adventure in Lake Michigan (up to 6 people)

(5 of 5 reviews)

Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking views of the city of Racine and on clear day views of Milwaukee and Kenosha You can lay back and relax to the sounds of the wave... More

Free Cancellation
Private Tour
Start From $126.00
 
2 Hour Sailing Adventure in Lake Michigan (up to 6 people) Likely to Sell Out

2 Hour Sailing Adventure in Lake Michigan (up to 6 people)

  • North America
  • Superb5 reviews5

Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking ....

    Free Cancellation
    Private Tour
    Start From $126.00
 
 

Sailing Tour around the Bacalar Lagoon

(4.8 of 11 reviews)

Embark on the adventure of knowing the Bacalar lagoon. Aboard our ranger 26, the Taan'ik (facing the wind in the Mayan language), we are at your disposal to offer you a unique experience. Visiting the lagoon of the 7 colors by sai... More

Free Cancellation
Private Tour
Start From $45.15
 
Sailing Tour around the Bacalar Lagoon Likely to Sell Out

Sailing Tour around the Bacalar Lagoon

  • North America
  • Superb11 reviews4.8

Embark on the adventure of knowing the Bacalar lagoon. Aboard our ranger 26, the Taan'ik (facing the....

    Free Cancellation
    Private Tour
    Start From $45.15
 
 

Wrightsville Beach Day Sail Private Catamaran Charter

(4.8 of 11 reviews)

On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islands and local spots. Upon anchoring, the crew will dinghy you around wherever you'd like to go! The boat is fully equipped with ai... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Wrightsville Beach Day Sail Private Catamaran Charter Likely to Sell Out

Wrightsville Beach Day Sail Private Catamaran Charter

  • North America
  • Superb11 reviews4.8

On this 4hr private charter, you will work with your captain to plan your perfect itinerary of islan....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Private Sailboat Guided Tour of New York City

(5 of 4 reviews)

Distinctively combine luxury, relaxation, adventure and education aboard a professionally guided private sailboat tour of the Hudson River & New York Harbor. Instead of a walking tour, sit and relax, as we serve you anything you b... More

Free Cancellation
Private Tour
Start From $1,330.00
 
Private Sailboat Guided Tour of New York City Likely to Sell Out

Private Sailboat Guided Tour of New York City

  • North America
  • Superb4 reviews5

Distinctively combine luxury, relaxation, adventure and education aboard a professionally guided pri....

    Free Cancellation
    Private Tour
    Start From $1,330.00
 
 

Sailing Charter around Vancouver Harbour Private Tour

(5 of 1 review)

Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and its surrounding inlets. Contagious is an Oceanis 46.1 and has all the features of a large cruising Yacht with a rare balance betw... More

Free Cancellation
Private Tour
Start From $2,341.19
 
Sailing Charter around Vancouver Harbour Private Tour Likely to Sell Out

Sailing Charter around Vancouver Harbour Private Tour

  • North America
  • Superb1 review5

Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and....

    Free Cancellation
    Private Tour
    Start From $2,341.19
 
 

The Hamptons Date Night Dining Hot Spots

(5 of 1 review)

This Hamptons hotspot dining boat tour allows guests to visit multiple dining hotspots in a single excursion hassle-free, maximizing their time and providing a convenient way to explore the Hamptons. Guests won't have to worry abo... More

Free Cancellation
Private Tour
Start From $1,790.00
 
The Hamptons Date Night Dining Hot Spots Likely to Sell Out

The Hamptons Date Night Dining Hot Spots

  • North America
  • Superb1 review5

This Hamptons hotspot dining boat tour allows guests to visit multiple dining hotspots in a single e....

    Free Cancellation
    Private Tour
    Start From $1,790.00
 
 

Luxury Private Sunset Experience in San Jose

(5 of 1 review)

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour. The Luxury Private Sailing boat have capacity from 1 to 16 people, the rate offered here is for 8 people, if like to add more pl... More

Free Cancellation
Private Tour
Start From $1,600.00
 
Luxury Private Sunset Experience in San Jose Likely to Sell Out

Luxury Private Sunset Experience in San Jose

  • North America
  • Superb1 review5

Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour....

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

Exclusive Private Sailing Luxury Tour in Los Cabos

(5 of 1 review)

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one of the best beach areas to discover the underwater world of the Los Cabos area. During the months of December thru March, you can w... More

Free Cancellation
Private Tour
Start From $1,600.00
 
Exclusive Private Sailing Luxury Tour in Los Cabos Likely to Sell Out

Exclusive Private Sailing Luxury Tour in Los Cabos

  • North America
  • Superb1 review5

Experience snorkeling in crystal waters, the beach Palmilla has a blue flag recognition and is one o....

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

Isla Mujeres Private Dream Getaway

(4.9 of 11 reviews)

If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres, the women’s Island. Your day starts with a transfer to the dock, where your guide will take you out by boat to the island of Is... More

Free Cancellation
Private Tour
Start From $545.00
 
Isla Mujeres Private Dream Getaway Likely to Sell Out

Isla Mujeres Private Dream Getaway

  • North America
  • Superb11 reviews4.9

If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres,....

    Free Cancellation
    Private Tour
    Start From $545.00
 
 

4 Hour Private Sail for up to 6 people

(5 of 11 reviews)

This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a customizable charter. Create your own adventure on a vintage sailing yacht for 4 hours with an experienced captain.... More

Free Cancellation
Private Tour
Start From $1,100.00
 
4 Hour Private Sail for up to 6 people Likely to Sell Out

4 Hour Private Sail for up to 6 people

  • North America
  • Superb11 reviews5

This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a c....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
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