Windjammer Cruises

Island Windjammers' Diamant
Island Windjammers' Diamant

Have you ever thought about taking a cruise on a tall ship? Windjammers feature a steel and/or iron hull with three to five large masts and square sails. They were originally designed to transport cargo in the 19th and early 20th century, and are one of the most beautiful sailing vessels that you can take a cruise on today. Windjammer cruises utilize restored historic sailing ships or replicas of these gorgeous vessels.

Windjammer Cruise Options

You may have heard the name Windjammer associated with Windjammer Barefoot Cruises, but they went out of business in 2007. Several companies offer windjammer cruises today. If you're interested in experiencing a windjammer cruise, there are a number of options. Information provided about cruise offerings is accurate as of January 2015. All prices are quoted in U.S. dollars. Contact the cruise company directly for current availability and pricing.

Island Windjammers

Island Windjammers offers cruises in the Caribbean on two different ships, the Diamant (12 passengers) and Sagitta (22 passengers). It was born from the ashes of Windjammer Barefoot Cruises.

What to Expect

Don't expect onboard entertainment and a buffet. These cruises are simple, small, and designed around the destination. Meals are served, but only basic alcohol is stocked, given space constraints. Unlike big cruise ships, you can bring on your own alcohol to mix your favorite drinks. The ship's saloon features a DVD player, board games, and playing cards.

These small ships fill up quickly so you should book no later than six months in advance.

Ports of Call

  • Ports of call in the Leeward Islands may include Anguilla, Antigua, Dominica, Guadeloupe, Iles des Saines, Martinique, Montserrat, Nevis, St. Barths, St. Eustatius, St. Kitts, St. Lucia, St. Maarten, and Tintamarre.
  • Windward Islands stops may include Bequia, Canouan, Carriacou, Grenada, Mayreau, Mustique, Petit St. Vincent, Sandy Island, St. Lucia, St. Vincent, Tobago Cays, Union Island, and Young Island.
  • U.S. and British Virgin Island itineraries may include Anguilla, Jost Van Dyke, Nevis, Norman Island, Salt Island, St. Barths, St. John, St. Kitts, St. Maarten, St. Thomas, Tortola, and Virgin Gorda.


Sample pricing (per person): A six-night cruise departing from St. Maarten in November is $1,700 for a solo cabin, $2,100 for a standard cabin, and $3,100 for an owner's suite.

Cruise fare includes meals, port taxes, government fees, snorkeling equipment, draft beer, wine, and soft drinks.

Maine Windjammer Cruises

Maine Windjammer Cruises is the original windjammer specialist, established back in 1936. Their ships, Grace Bailey and the Mercantile, were old cargo windjammers that have been outfitted for sailing vacations now. They are traditional, no-motor ships.

Cruise Options

Cruises depart from Camden, Maine and sail around the state's islands. With Maine Windjammer Cruises you can book several different types of cruises, depending on the season.

Pre-season cruises are offered late-May through mid-June and include options like:

  • Season starters: Shakedown weekend, Victoria 4-Day Cruise, Memorial Day Weekend
  • Three-day pre-season: Choose from first or second half of the week
  • Six-day pre-season: Board Sunday and return by Saturday

During the summer months, there are three, four, and five day cruises available. If you're short on time, consider a weekend cruise. Board Friday afternoon and return Sunday morning. As the season winds down, consider a fall foliage cruise.


Sample pricing (per person): A three-day pre-season cruise in June is $545, while a five-day cruise on the Grace Bailey will run you $845 throughout the summer.

Fares on Maine Windjammer Cruises include meals and non-alcoholic beverages. A cooler and ice are available at all times and you can bring your own alcohol and carbonated drinks.

Sail Windjammer

Sail Windjammer offers Caribbean itineraries aboard the SV Mandalay. Accommodations on the SV Mandalay are comfortable. Cabins vary in size, location, and price, but include comforts like a private shower, wardrobe space, steward service, and air-conditioning.

Ports of Call

Cruises depart Grenada and include ports like Bequia, Chatham Bay on Union Island, Mayreau, Tobago Cays, Carriacou, and Sandy Island.


Sample pricing (per person): Standard cabins below deck with bunk beds start at $1,599 for one week and $2,800 for two weeks. King cabins start at $1,899 for one week and $3,400 for two weeks.

Cruise fare includes three meals per day, on-board entertainment, early morning pastries, bloody Marys, evening snacks, rum swizzles, wine with dinner, and 24-hour coffee and tea. Port charges are $99 for a one week cruise and $149 for a two week cruise.

Liberty Fleet

Liberty Fleet was founded in 1995 and offers week-long windjammer cruises aboard the TALOFA and the Liberty Clipper from various ports. The ships have masks and snorkels, along with kayaks that guests can use.

Cruise Options

  • The TALFOA is a 97-foot wooden schooner featuring three cabins. It sails the Virgin Islands from November through May.
  • The Liberty Clipper is a 125-foot gaff-rigged schooner with 12 cabins in three different classes. Choose from itineraries in the Bahamas, Chesapeake Bay, or New England.
    • The ship is in the Bahamas from late November to early May, Boston in the summer, and Chesapeake Bay in the fall.
    • For a truly unique experience, get in on one of the repositioning cruises. In May, the ship heads from the Bahamas to Charleston, then on to Boston. In early October, the Liberty Clipper leaves Chesapeake Bay, stops in Charleston and then makes its way back to the Bahamas.


Sample pricing (per person): A six-night Bahamas sailing cruise starts at $1,249, while six-night Virgin Island cruises start at $1,850.

Meals, water, juice, coffee and tea are included in cruise fare. Alcohol, canned soda and bottled water are extra. Guests cannot consume their own alcohol aboard the boat.

A Different Kind of Cruise

Cruising on a Windjammer is a unique experience from cruising on a large ship. If you want big buffets, endless casino games, and nightclubs, you are likely to be very disappointed. Meal options are limited, but the food is typically excellent. Some windjammer cruises include limited alcohol, while others allow you to bring your own.

Benefits of Cruising on a Windjammer

The ability to visit ports large cruise ships can't is an important benefit of cruising on a small windjammer. Additionally, in many cases, these cruises have no set itinerary. There is ample opportunity to find yourself docking in completely unexpected ports or staying longer to witness an incredible sunset.

The best benefit of cruising on a windjammer is the ability to completely unwind. Relax on the calm seas as you sail between islands, jump in the shallow water and go snorkeling, or hop on a kayak and go exploring. You can even help with crewing the ship, if you are so inclined. Adventure awaits at every stop on a windjammer cruise, minus the typical tourist traps and overcrowded beaches.

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