Tall Ship Windjammer Cruise
Sailing Vacations

Windjammer Sailing Vacation CruisesWindjammer Cruises...

Windjammer cruise sailing vacations with the Liberty Fleet are a cruise aboard historic tall ships. You will be welcomed aboard by our professional crew who are there to ensure your safety and enjoyment on your sailing cruise. A windjammer sailing cruise is a unique tall ship experience where the destinations are influenced by the winds and tides to provide the ultimate relaxation and peacefulness on the water. If you want excitement, the crew will welcome you to help raise the sails, learn navigation and participate in the sailing of the ship. You can join the captain at the helm and look forward over our ships as they drive forward under a canopy of sail billowing above you... 


Breakfast on a tall shipWe maintain a professional cook aboard the ship during your sailing cruise to provide home-cooked meals daily. All of our windjammer cruises will also feature wonderful food and offer seasonal local favorites that can include fish or lobster. Start each day right with a steaming pot of coffee or tea and enjoy the delights that our galley will put out daily from fresh breads, local seafood, fruits and other local favorites. The Liberty Clipper is renowned for her great fare and guests will never leave hungry.


Great FoodLunch on Deck


A Typical Day on a Windjammer Cruise...

Dolphins Swimming in the WakeWake each day of your sailing vacation to the gentle sounds of water lapping against the hull, sea birds looking for their morning meal, and the gentle sway of the ship at anchor. Your day will start with a wonderful breakfast served on the main deck at your leisure. With fresh brewed coffee, fruits, breads, and any combination from waffles to cereal, you'll find something to start your day off right! After a relaxing start, we will begin the day's sail. Typically the ship will sail from mid-morning to mid-afternoon. The day is your time to relax, take a cat-nap, read a good book, listen to the captain tell sea stories or help sail the ship.


Relaxing on a WindjammerOn your sailing cruise, you may find that just relaxing on the main deck is how you'd prefer to spend your afternoon - that's fine! Pick anyplace you like and make yourself at home.


While not required, you are always invited to get involved with the sailing of the ship. Our professional crew will help you plot our course on a nautical chart, haul away on the sails, take a turn at the helm or even climb the rigging and sit atop the masts! We're here for your enjoyment, so just let us know how we can make your tall ship cruise more enjoyable! We love tall ships and can't wait to share that passion with you.


Climbing Aloft1 MorningSailJumping Over


Jumping Off the WindjammerOnce we've anchored for the afternoon, you have access to the world's largest swimming pool! Feel free to jump in - cannonball or dive, your choice! We have a ladder available for you to get back aboard. Our crew will also be on hand to assist you if you need anything - we are here to help!


Have fun ashore on your windjammer tall ship cruiseYou will also have the opportunity to head ashore each day of your tall ship cruise. Depending upon which tall ship cruise you select, you may find yourself on a tropical beach, exploring an historic fort or touring in our kayaks. Each day will present unique opportunities for you to discover local culture and wildlife. A windjammer cruise on the Liberty Clipper provides you opportunities to truly explore off-the-beaten path locations like you'd never imagined...


Tall Ship SunsetsIn the evenings, you will enjoy fine homemade meals prepared by our cooks. You can relax aboard the ship, or stay ashore a little longer, again depending upon the itinerary of your cruise. Sunsets on the water are always amazing... When it's time to turn in for the evening, your comfortable cabin awaits...


Video courtesy of Two for the Road, Nikki & Dusty Greene.

We invite you to learn more about our unique style of cruising. Please explore our website

  • Schedule and online booking
  • Sailing Ships
    • Liberty Clipper: Our 125-foot, 24-guest flagship sails the Bahamas and New England Coast.
    • Liberty Star: Our 67-foot, 6-guest tall ship sails the US & British Virgin Islands.
  • Destinations
    • Bahamas: Sail the Bahamas for a tall ship cruising vacation to the Out Islands aboard Liberty Clipper.
    • Virgin Islands: Join us for an exciting sail in the US & British Virgin Islands aboard Liberty Star.
  • Blog & Guest Reviews: See what past cruisers have said about their trips
  • Photo Gallery: View videos and pictures of our cruises