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Top 10 Best North America Sailing Trips

Found 723 Sailing Trips activities in North America. Sort by Popularity. - Page 32
 

Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks

(5 of 1 review)

Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing catamaran. Explore the island through authentic storytelling, coastal beauty, and handcrafted island specialties, both sippable and sa... More

Free Cancellation
Start From $159.00
 
Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks

Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks

  • North America
  • Superb1 review5

Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing cata....

    Free Cancellation
    Start From $159.00
 
 

Private Sailing Experience along the Southern Maine Coastline

(5 of 1 review)

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of six guests, this exclusive journey allows you to soak in the stunning scenery while learning about the rich history of the area, i... More

Free Cancellation
Private Tour
Start From $747.00
 
Private Sailing Experience along the Southern Maine Coastline

Private Sailing Experience along the Southern Maine Coastline

  • North America
  • Superb1 review5

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of ....

    Free Cancellation
    Private Tour
    Start From $747.00
 
 

Private 43' Azimut Yacht 4h – Drinks & Food Included

(5 of 6 reviews)

What truly sets this tour apart is the level of privacy and customization we offer. Whether you're celebrating a special occasion or simply seeking a luxurious escape, our crew tailors every detail to your preferences — from the... More

Free Cancellation
Private Tour
Start From $1,705.00
 
Private 43' Azimut Yacht 4h – Drinks & Food Included

Private 43' Azimut Yacht 4h – Drinks & Food Included

  • North America
  • Superb6 reviews5

What truly sets this tour apart is the level of privacy and customization we offer. Whether you're c....

    Free Cancellation
    Private Tour
    Start From $1,705.00
 
 

3 in 1 Snorkeling, Parasailing, with Turtle

(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 $159.00
 
3 in 1 Snorkeling, Parasailing, with Turtle

3 in 1 Snorkeling, Parasailing, with Turtle

  • 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 $159.00
 
 

Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay

(5 of 1 review)

This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become part of the crew. Our goal is to perform as a unit and get the boat to sail as fast as possible. However, if you are looking for a mo... More

Free Cancellation
Private Tour
Start From $600.00
 
Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay

Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay

  • North America
  • Superb1 review5

This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become par....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Sunset Boat Tour on Baja Blast Includes Open Bar and Dinner

(5 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 $99.00
 
Sunset Boat Tour on Baja Blast Includes Open Bar and Dinner

Sunset Boat Tour on Baja Blast Includes Open Bar and Dinner

  • North America
  • Superb1 review5

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 $99.00
 
 

Los Cabos Catamaran Private Sunset Sail with Snorkel Gear

(5 of 1 review)

Enjoy a fully private catamaran cruise where your group has the entire vessel to yourselves—no crowds, just personalized VIP service. Sail past Los Cabos’ most iconic landmarks, including El Arco, Lover’s Beach, and the Sea ... More

Free Cancellation
Private Tour
Start From $1,295.00
 
Los Cabos Catamaran Private Sunset Sail with Snorkel Gear Likely to Sell Out

Los Cabos Catamaran Private Sunset Sail with Snorkel Gear

  • North America
  • Superb1 review5

Enjoy a fully private catamaran cruise where your group has the entire vessel to yourselves—no cro....

    Free Cancellation
    Private Tour
    Start From $1,295.00
 
 

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
 
 

Private Isla Mujeres Adventure & Free Time

(4.9 of 12 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 ... More

Free Cancellation
Private Tour
Start From $545.00
 
Private Isla Mujeres Adventure & Free Time Likely to Sell Out

Private Isla Mujeres Adventure & Free Time

  • North America
  • Superb12 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
 
 

Full-Day Sailing Adventure to Isla Mujeres

(3.5 of 4 reviews)

This 7-hour tour is the best way to enjoy "the life aquatic" of the Cancun coast. Sail from Cancun to Isla Mujeres aboard a wind-powered catamaran with an experienced and friendly captain and crew. Lounge, swim, eat, and drink at ... More

Free Cancellation
Private Tour
Start From $49.99
 
Full-Day Sailing Adventure to Isla Mujeres Likely to Sell Out

Full-Day Sailing Adventure to Isla Mujeres

  • North America
  • Good4 reviews3.5

This 7-hour tour is the best way to enjoy "the life aquatic" of the Cancun coast. Sail from Cancun t....

    Free Cancellation
    Private Tour
    Start From $49.99
 
 

Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers

(3.5 of 4 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 Likely to Sell Out

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

  • North America
  • Good4 reviews3.5

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
 
 

Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran

(3.5 of 4 reviews)

Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sail through the stunning waters of Los Cabos, immerse yourself in breathtaking views at every turn — from the iconic Lover’s Bea... More

Free Cancellation
Private Tour
Start From $135.00
 
Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran Likely to Sell Out

Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran

  • North America
  • Good4 reviews3.5

Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sai....

    Free Cancellation
    Private Tour
    Start From $135.00
 
 

Chesapeake Bay Private Cruise

(4.4 of 7 reviews)

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water, or just to have the cruise to yourself! Enjoy the peaceful sounds of the waves gently breaking off the hul... More

Free Cancellation
Private Tour
Start From $651.00
 
Chesapeake Bay Private Cruise Likely to Sell Out

Chesapeake Bay Private Cruise

  • North America
  • Exellent7 reviews4.4

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guy....

    Free Cancellation
    Private Tour
    Start From $651.00
 
 

Afternoon Kealakekua Snorkel and Sail

(5 of 11 reviews)

Join us for a sensational 3.5 hour coastal sail, which includes snorkeling in the marine sanctuary of Kealakekua Bay (home of the Captain Cook Monument). Explore the incredible world under the water with its abundance of marine li... More

Free Cancellation
Private Tour
Start From $189.00
 
Afternoon Kealakekua Snorkel and Sail Likely to Sell Out

Afternoon Kealakekua Snorkel and Sail

  • North America
  • Superb11 reviews5

Join us for a sensational 3.5 hour coastal sail, which includes snorkeling in the marine sanctuary o....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

(3.7 of 3 reviews)

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in the South's picturesque setting, this 2-hour sail gives yo... More

Free Cancellation
Private Tour
Start From $38.00
 
Morning Charleston Harbor Sail Lux Catamaran Shade and Seating Likely to Sell Out

Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

  • North America
  • Very Good3 reviews3.7

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the....

    Free Cancellation
    Private Tour
    Start From $38.00
 
 

Private Luxury Yacht for up to 12 people

(3.7 of 3 reviews)

A whole nautical experience awaits you on board the Sea Ray 440, nothing is missing, comfortable, luxurious and sophisticated, it is specially designed to satisfy the demands of the best tastes and turn moments into memories that ... More

Free Cancellation
Private Tour
Start From $3,250.00
 
Private Luxury Yacht for up to 12 people Likely to Sell Out

Private Luxury Yacht for up to 12 people

  • North America
  • Very Good3 reviews3.7

A whole nautical experience awaits you on board the Sea Ray 440, nothing is missing, comfortable, lu....

    Free Cancellation
    Private Tour
    Start From $3,250.00
 
 

Private Sunset Sail in Key West Florida

(3.7 of 3 reviews)

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
  • Very Good3 reviews3.7

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
 
 

JFarwell Private Yacht Wine & Cheese Sunset Sail

(4.9 of 18 reviews)

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests will be greeting with their first Nova Scotia wine upon boarding, and then set sail. With the engines off and fully under wind power,... More

Free Cancellation
Private Tour
Start From $148.52
 
JFarwell Private Yacht Wine & Cheese Sunset Sail Likely to Sell Out

JFarwell Private Yacht Wine & Cheese Sunset Sail

  • North America
  • Superb18 reviews4.9

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests wil....

    Free Cancellation
    Private Tour
    Start From $148.52
 
 

Land’s End Sunset Cruise – Open Bar & Tacos Included

(4.9 of 18 reviews)

Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, with approximately 40 minutes spent at each captivating point along the route. As you glide through the stunning landscapes of Cab... More

Free Cancellation
Private Tour
Start From $140.00
 
Land’s End Sunset Cruise – Open Bar & Tacos Included Likely to Sell Out

Land’s End Sunset Cruise – Open Bar & Tacos Included

  • North America
  • Superb18 reviews4.9

Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, w....

    Free Cancellation
    Private Tour
    Start From $140.00
 
 

Private Swim and Sail Charter (Kewalo Harbor)

(4.9 of 18 reviews)

A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). This experience is customization in its duration and activity *Viewing marine life is not guaranteed but we do... More

Free Cancellation
Private Tour
Start From $1,800.00
 
Private Swim and Sail Charter (Kewalo Harbor) Likely to Sell Out

Private Swim and Sail Charter (Kewalo Harbor)

  • North America
  • Superb18 reviews4.9

A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and....

    Free Cancellation
    Private Tour
    Start From $1,800.00
 
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