Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 668 Sailing Trips activities in North America. Sort by Popularity. - Page 7Sunset Sail On A Charming Vintage Yacht - Beer &. Wine Included
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica of a 1904 gaff rigged friendship sloop. She is an elegant sight under sail, featuring; highly finished woodwork, bronze fixtures, a... More

Sunset Sail On A Charming Vintage Yacht - Beer &. Wine Included
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North America
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Superb287 reviews4.9
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....
Suncoast Sailing's Sunset Sailing Experience!
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More

Suncoast Sailing's Sunset Sailing Experience!
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North America
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Superb221 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)
Join us on Cozumel's largest and most luxurious catamaran with the First Lady Charters Team! Embark on a guided snorkeling tour at Cozumel's renowned Marine Park Reef, with all necessary snorkeling gear provided in different sizes... More
Private Tour

Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)
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North America
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Superb12 reviews4.7
Join us on Cozumel's largest and most luxurious catamaran with the First Lady Charters Team! Embark ....
Private Tour
El Cielo Cozumel Snorkeling by Catamaran
TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head back to a secluded Beach to relax and enjoy the beauty of Cozumel turquoise waters.... More
Private Tour

El Cielo Cozumel Snorkeling by Catamaran
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North America
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Exellent273 reviews4.4
TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....
Private Tour
2-Hour Seattle Sailing Harbor Tour
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More
Private Tour

2-Hour Seattle Sailing Harbor Tour
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North America
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Superb374 reviews4.7
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....
Private Tour
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More
Private Tour

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique
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North America
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Superb27 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Half Day Luxury Sailing Experience in Riviera Maya with Open Bar
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More
Private Tour

Half Day Luxury Sailing Experience in Riviera Maya with Open Bar
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North America
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Exellent60 reviews4.4
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Private Tour
Sunset Sail Aboard the 47 ft Daydreams Sailboat
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More
Private Tour

Sunset Sail Aboard the 47 ft Daydreams Sailboat
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North America
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Superb12 reviews4.8
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....
Private Tour
Boat Tour and Snorkel at Pelican Rock
The must do activities in Cabo are tour the arch, whale watching and snorkeling. We have put all of those things in one spot in this bucket list level experience. First take a boat tour of all of the landmarks Cabo boasts on the w... More
Private Tour

Boat Tour and Snorkel at Pelican Rock
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North America
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Exellent12 reviews4.3
The must do activities in Cabo are tour the arch, whale watching and snorkeling. We have put all of ....
Private Tour
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar
Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful tropical fish. Enjoy a delicious buffet lunch on our private beach club, and then tour Isla Mujeres to s... More
Private Tour

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar
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North America
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Very Good201 reviews3.7
Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....
Private Tour
Private Sailing Tour through the Ten Thousands Islands
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More
Private Tour

Private Sailing Tour through the Ten Thousands Islands
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North America
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Superb140 reviews4.9
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....
Private Tour
Luxury Catamaran Whale Watch
Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback whale. The waters off West Maui have long been the favored vacation spot of these massive marine mammals. The Alii Class Yachts pro... More
Private Tour

Luxury Catamaran Whale Watch
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North America
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Superb39 reviews5
Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback w....
Private Tour
4-Hour St. Pete Pier to Egmont Key Experience by Ferry
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a dolphin or two! This is the only charter offering service from downtown St. Petersb... More
Private Tour

4-Hour St. Pete Pier to Egmont Key Experience by Ferry
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North America
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Superb289 reviews4.7
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....
Private Tour
Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!
Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in the Puget Sound. This personalized voyage is designed for up to six passengers, offering an intimate and unforgettable experience ... More
Private Tour

Seattle's Best Private Sailing Adventure on the Puget Sound BYOB!
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North America
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Superb104 reviews5
Escape the hustle and bustle of city life and embark on an exclusive 3-hour private sailing tour in ....
Private Tour
Small Group Waikiki Sunset Sailing Tour
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More
Private Tour

Small Group Waikiki Sunset Sailing Tour
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North America
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Superb90 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
Private Tour
Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a delicious drink and the entertainment from the crew. Unique and quality service is our priority. We are sure that you will love all... More
Private Tour

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
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North America
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Exellent286 reviews4.4
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a d....
Private Tour
Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews on Google. What you will get: Nature Immersion: Encounter dolphins, turtles, manatees, and more as you explore Miami's waters Cel... More
Private Tour

Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun
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North America
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Superb56 reviews4.7
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews ....
Private Tour
Monterey Bay Whale Watching
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More
Private Tour

Monterey Bay Whale Watching
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North America
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Superb277 reviews4.7
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....
Private Tour
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convert... More
Private Tour

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
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North America
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Superb11 reviews4.9
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....
Private Tour
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More
Private Tour

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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North America
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Superb22 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Private Tour