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Top 10 Best North America Sailing Trips

Found 723 Sailing Trips activities in North America. Sort by Popularity. - Page 32
 
-20% Sunset Boat Tour Includes Open Bar and Dinner

Sunset Boat Tour Includes Open Bar and Dinner

(3.5 of 2 reviews)

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

Special Offer
Free Cancellation
Start From $79.20
(Saving 20% ) $99.00
 
-20% Sunset Boat Tour Includes Open Bar and Dinner

Sunset Boat Tour Includes Open Bar and Dinner

  • North America
  • Good2 reviews3.5

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

    Special Offer
    Free Cancellation
    Start From $79.20
    (Saving 20% ) $99.00
 
 

Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay

(3.5 of 2 reviews)

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
  • Good2 reviews3.5

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
 
 

Private Luxury Yacht in Miami

(3.5 of 2 reviews)

️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s top destinations—Haulover Sandbar, Oleta River State Park, Biscayne Bay & Sands Key, and Raccoon Island—in style! This sleek 3... More

Free Cancellation
Private Tour
Start From $830.00
 
Private Luxury Yacht in Miami

Private Luxury Yacht in Miami

  • North America
  • Good2 reviews3.5

️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s ....

    Free Cancellation
    Private Tour
    Start From $830.00
 
 

Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers

(3.5 of 2 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
  • Good2 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
 
 

Private Charter Snorkel Sail Adventure off Kaanapali Beach

(3.5 of 2 reviews)

PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘H... More

Free Cancellation
Private Tour
Start From $6,301.24
 
Private Charter Snorkel Sail Adventure off Kaanapali Beach

Private Charter Snorkel Sail Adventure off Kaanapali Beach

  • North America
  • Good2 reviews3.5

PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....

    Free Cancellation
    Private Tour
    Start From $6,301.24
 
 

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

(3.5 of 2 reviews)

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

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

  • North America
  • Good2 reviews3.5

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

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
 
 

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
Private Tour
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
    Private Tour
    Start From $159.00
 
 

Private Swim and Sail Charter (Kewalo Harbor)

(5 of 1 review)

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)

Private Swim and Sail Charter (Kewalo Harbor)

  • North America
  • Superb1 review5

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
 
 

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

(5 of 1 review)

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

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

  • North America
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $140.00
 
 

Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran

(5 of 1 review)

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

Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran

  • North America
  • Superb1 review5

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
 
 

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
 
 

Private Luxury Yacht for up to 12 people

(5 of 6 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

Private Luxury Yacht for up to 12 people

  • North America
  • Superb6 reviews5

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
 
 

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

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
 
 

Waikiki private Day Tour and Sunset sail for couples

(5 of 16 reviews)

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples on their honeymoon, celebrating an Anniversary, or just in love, celebrating ... More

Free Cancellation
Private Tour
Start From $300.00
 
Waikiki private Day Tour and Sunset sail for couples Likely to Sell Out

Waikiki private Day Tour and Sunset sail for couples

  • North America
  • Superb16 reviews5

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

Private 3 hour Bird Watching Tour in Monterey Bay

(5 of 1 review)

Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail is much quieter and therefore up close encounters with seabirds are common. This tour is great for birders who are looking for an ... More

Free Cancellation
Private Tour
Start From $950.00
 
Private 3 hour Bird Watching Tour in Monterey Bay Likely to Sell Out

Private 3 hour Bird Watching Tour in Monterey Bay

  • North America
  • Superb1 review5

Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail ....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Private Dolphin Catamaran Sail In Cocoa Beach

(5 of 1 review)

Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter playful dolph... More

Free Cancellation
Private Tour
Start From $337.87
 
Private Dolphin Catamaran Sail In Cocoa Beach Likely to Sell Out

Private Dolphin Catamaran Sail In Cocoa Beach

  • North America
  • Superb1 review5

Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforg....

    Free Cancellation
    Private Tour
    Start From $337.87
 
 

Two Hour Private Sailing Charter

(5 of 3 reviews)

Escape the city on a two hour private sailing charter for up to 6 guests. Our two hour charter option is available morning, afternoon, and evening, and it is a great option for a quick getaway. We sail you around lower Manhattan w... More

Free Cancellation
Private Tour
Start From $625.00
 
Two Hour Private Sailing Charter Likely to Sell Out

Two Hour Private Sailing Charter

  • North America
  • Superb3 reviews5

Escape the city on a two hour private sailing charter for up to 6 guests. Our two hour charter optio....

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests

(3.5 of 2 reviews)

A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sailing charters and boat tours. Sail San Diego with us. Our sa... More

Free Cancellation
Private Tour
Start From $115.00
 
Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests Likely to Sell Out

Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guest....

  • North America
  • Good2 reviews3.5

A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San D....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

Unlimited Catamaran to Isla Mujeres from Cancun

(3.5 of 2 reviews)

Your journey begins at the breathtaking Punta Sam Reef, where you'll dive into your first snorkeling experience and discover the vibrant underwater world of the Caribbean. Then, set sail along the stunning coastline toward Punta... More

Free Cancellation
Private Tour
Start From $85.00
 
Unlimited Catamaran to Isla Mujeres from Cancun Likely to Sell Out

Unlimited Catamaran to Isla Mujeres from Cancun

  • North America
  • Good2 reviews3.5

Your journey begins at the breathtaking Punta Sam Reef, where you'll dive into your first snorkeling....

    Free Cancellation
    Private Tour
    Start From $85.00
 
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