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Island Windjammers Cruises


About Island Windjammers Cruises

Island Windjammers offers small-ship cruises that are focused more on the joys of sailing than on shipboard amenities. Passengers can even take a turn at the helm of one of the cruise line's three ships. Casual and social onboard atmosphere.

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Save 50-75% On Caribbean/Bahamas Cruises
3, 4 & 7-night cruises from Miami or Orlando
  • Save 50-75% on 2021 Caribbean & Bahamas cruises
  • PLUS Kids Sail Free*
  • PLUS Total CruiseFlex - Complete Change Flexibility up to 48 hrs
  • Explore Ocean Cay, our exclusive private island with 8 beaches
MSC Cruises

Awards and Recognition

Cruise Critic Cruisers’ Choice Destination

  • 2017 Top-Rated Eastern Caribbean, Bahamas & Bermuda Destinations
  • 2017 Top-Rated Southern Caribbean Destinations

Who goes on Island Windjammers cruise ships?

Come prepared to socialize; with no more than 30 passengers onboard, it's hard to be anti-social on an Island Windjammers sailing. Most cruisers are a mix of solo travelers, friends traveling together and couples. While most passengers fall into the 45- to 65-year-old age range, there usually is a sprinkling of older and younger passengers. The company also attracts families onboard, as it welcomes children 8 and up year-round, except for a few themed cruises, and offers discounted youth fares in the summer. (Given the size of the ships, families often charter an entire ship -- or part of a ship -- for a family reunion.)

Do I have to dress up on a Island Windjammers cruise?

No, Island Windjammers wholeheartedly embraces the concept of casual cruising. Swimsuits, cover-ups and T-shirts are typical daytime attire, and dressing for dinner usually means nothing more than putting on a clean shirt.

Is everything free on Island Windjammers cruises?

Not quite. Island Windjammers' cruise fares include all meals and snacks, beverages (beer, wine, rum punch, soft drinks and tonic water) and the use of snorkeling equipment.

Shore excursions and gratuities cost extra, and there is no Wi-Fi onboard.

What are Island Windjammers’s most popular activities?

Island Windjammers' ships are intentionally short on typical cruise ship amenities, such as fitness centers and theaters, with passengers preferring to relax or if they're feeling up to it, help to raise the sails and even take a turn at the helm.

The upper deck is a popular place to congregate; passengers use its cushioned benches to chat and nap. You can also swim and snorkel directly from the ship. The more adventurous opt for the stand-up paddle-boards or the rope swing.

The flexible Windjammer schedule leaves plenty of time to explore on land, and cruisers enjoy hiking, swimming, snorkeling and checking out the colorful smaller islands the ships visit.

Why go with Island Windjammers?

Three windjammer-style tall ships that carry 10 to 30 passengers

Best for: Those who dream of exploring the world under sail and enjoy the company of like-minded travelers

Not for: Cruisers looking for production shows, lavish onboard amenities or to be connected 24/7

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Lowest pricing is based on our 3rd party pricing supplier and valid as of October 31st, 2020.

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