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Top 10 Best North America Sailing Trips

Found 672 Sailing Trips activities in North America. Sort by Popularity. - Page 10
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 332 reviews)

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Free Cancellation
Start From $64.95
 
Windjammer Classic Sunset Sail from Camden, Maine

Windjammer Classic Sunset Sail from Camden, Maine

  • North America
  • Superb332 reviews4.9

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....

    Free Cancellation
    Start From $64.95
 
 

Statue of Liberty Sunset Cruise and New York City Sky Line

(3.1 of 38 reviews)

New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View of the Manhattan skyline, One World Trade Center and the Empire State Building.Enjoy a panoramic view of lower Manhattan as you p... More

Free Cancellation
Start From $35.00
 
Statue of Liberty Sunset Cruise and New York City Sky Line

Statue of Liberty Sunset Cruise and New York City Sky Line

  • North America
  • Good38 reviews3.1

New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View....

    Free Cancellation
    Start From $35.00
 
 

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

(5 of 46 reviews)

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More

Free Cancellation
Start From $119.00
 
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

  • North America
  • Superb46 reviews5

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....

    Free Cancellation
    Start From $119.00
 
 

Sailing Tour through the Laguna de los Siete Colores

(5 of 1,342 reviews)

Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical place without damaging the ecosystem. Guided by a team of professionals, with whom you ... More

Free Cancellation
Start From $38.00
 
Sailing Tour through the Laguna de los Siete Colores

Sailing Tour through the Laguna de los Siete Colores

  • North America
  • Superb1,342 reviews5

Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....

    Free Cancellation
    Start From $38.00
 
 

Reef Snorkel, underwater adventure in Puerto Morelos With Transportation & Lunch

(4 of 3 reviews)

Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a must activity in Cancun. You will visit one of the most bigger reef in the world, this is consider as the 2nd one worldwide. Imagi... More

Free Cancellation
Start From $55.00
 
Reef Snorkel, underwater adventure in Puerto Morelos With Transportation & Lunch Likely to Sell Out

Reef Snorkel, underwater adventure in Puerto Morelos With Transpo....

  • North America
  • Very Good3 reviews4

Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a mu....

    Free Cancellation
    Start From $55.00
 
 

Sunset Sail Cruise in Key West

(4.9 of 219 reviews)

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Free Cancellation
Start From $95.00
 
Sunset Sail Cruise in Key West Likely to Sell Out

Sunset Sail Cruise in Key West

  • North America
  • Superb219 reviews4.9

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....

    Free Cancellation
    Start From $95.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 226 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More

Free Cancellation
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb226 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Start From $136.19
 
 

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

(4.6 of 12 reviews)

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and family to see all the iconic waterfront sights of Newport and Narraganset... More

Free Cancellation
Start From $57.24
 
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport Likely to Sell Out

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

  • North America
  • Superb12 reviews4.6

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard ....

    Free Cancellation
    Start From $57.24
 
 

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure

(4.5 of 70 reviews)

Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This is the tour for you! Enjoy sailing in one of our Catamarans and we will ensure that you enjoy your afternoon to the maximum. We wi... More

Free Cancellation
Start From $69.99
 
Afternoon Half-Day Catmaran Sailing and Snorkel Adventure Likely to Sell Out

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure

  • North America
  • Exellent70 reviews4.5

Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This ....

    Free Cancellation
    Start From $69.99
 
 

Private Charleston Harbor Catamaran Sail

(5 of 26 reviews)

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a panoramic view with large sliding glass doors between the saloon and the rear deck space, with... More

Free Cancellation
Private Tour
Start From $950.00
 
Private Charleston Harbor Catamaran Sail Likely to Sell Out

Private Charleston Harbor Catamaran Sail

  • North America
  • Superb26 reviews5

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing cata....

    Free Cancellation
    Private Tour
    Start From $950.00
 
 

Tour to Arch in the Clear Boat Cruise Ship Terminal Hotel PICKUP!

(4.8 of 5 reviews)

Enjoy the most popular experience in Cabo in our 100% transparent boat! A unique experience in the world where you will get to know the famous arch, the incredible rock formations, tropical fish, reefs, the love and divorce beach,... More

Free Cancellation
Skip The Line
Private Tour
Start From $24.85
 
Tour to Arch in the Clear Boat Cruise Ship Terminal Hotel PICKUP! Likely to Sell Out

Tour to Arch in the Clear Boat Cruise Ship Terminal Hotel PICKUP!

  • North America
  • Superb5 reviews4.8

Enjoy the most popular experience in Cabo in our 100% transparent boat! A unique experience in the w....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $24.85
 
 

Tall Ship Silva Sailing Cruise

(4.1 of 203 reviews)

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our comfortable and thoroughly impressive vessel for this relaxing afternoon outing on the water. Your j... More

Free Cancellation
Skip The Line
Private Tour
Start From $44.07
 
Tall Ship Silva Sailing Cruise Likely to Sell Out

Tall Ship Silva Sailing Cruise

  • North America
  • Exellent203 reviews4.1

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Ha....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $44.07
 
 

Tour to The Arch and Lover's Beach (optional) from Cabo

(5 of 4 reviews)

This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, and through the Marina. See it all in one tour! During this awesome experience, you will be able to see a great variety of tropical... More

Free Cancellation
Skip The Line
Private Tour
Start From $30.00
 
Tour to The Arch and Lover's Beach (optional) from Cabo Likely to Sell Out

Tour to The Arch and Lover's Beach (optional) from Cabo

  • North America
  • Superb4 reviews5

This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, a....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $30.00
 
 

Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling

(4.9 of 107 reviews)

Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Vallarta´s Bay. You will be able to Sail, Snorkel, Swim and even Paddelboard in Los Arcos National Park, capturing beautiful views ... More

Free Cancellation
Skip The Line
Private Tour
Start From $758.67
 
Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling Likely to Sell Out

Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling

  • North America
  • Superb107 reviews4.9

Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Va....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $758.67
 
 

Private Catamaran Charter in Waikiki (7-12 Guests)

(4.9 of 107 reviews)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More

Free Cancellation
Skip The Line
Private Tour
Start From $1,200.00
 
Private Catamaran Charter in Waikiki (7-12 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (7-12 Guests)

  • North America
  • Superb107 reviews4.9

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $1,200.00
 
 

All Inclusive Tulum: 4 hrs Private in 40' Catamaran Bali

(5 of 278 reviews)

It is an incredible and unique experiences because for 4 hours you will be the owner of this incredible sailing catamaran, with a host and a chef at your disposal, the captain will take you to sail in the most beautiful waters of ... More

Free Cancellation
Skip The Line
Private Tour
Start From $2,100.00
 
All Inclusive Tulum: 4 hrs Private in 40' Catamaran Bali Likely to Sell Out

All Inclusive Tulum: 4 hrs Private in 40' Catamaran Bali

  • North America
  • Superb278 reviews5

It is an incredible and unique experiences because for 4 hours you will be the owner of this incredi....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $2,100.00
 
 

Private Morning Sailing/Dolphin & History Tours on 43ft Mystique

(5 of 72 reviews)

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

Free Cancellation
Skip The Line
Private Tour
Start From $499.00
 
Private Morning Sailing/Dolphin & History Tours on 43ft Mystique Likely to Sell Out

Private Morning Sailing/Dolphin & History Tours on 43ft Mystique

  • North America
  • Superb72 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $499.00
 
 

Private sailing tour of Bacalar Lagoon

(5 of 297 reviews)

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More

Free Cancellation
Skip The Line
Private Tour
Start From $205.00
 
Private sailing tour of Bacalar Lagoon Likely to Sell Out

Private sailing tour of Bacalar Lagoon

  • North America
  • Superb297 reviews5

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $205.00
 
 

6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beaches

(5 of 12 reviews)

Sail on a private trip aboard our 50-foot private yacht, ideal for up to 18 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer you to make... More

Free Cancellation
Skip The Line
Private Tour
Start From $1,381.25
 
6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beaches Likely to Sell Out

6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beac....

  • North America
  • Superb12 reviews5

Sail on a private trip aboard our 50-foot private yacht, ideal for up to 18 passengers. We are sure ....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $1,381.25
 
 

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

(4.9 of 10 reviews)

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment to sustainability and having a minimal impact on the environment ! It is a wholesome adventure that will le... More

Free Cancellation
Skip The Line
Private Tour
Start From $500.00
 
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay Likely to Sell Out

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

  • North America
  • Superb10 reviews4.9

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We ....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $500.00
 
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