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Island Windjammers Cruises

151 Reviews

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.

  • More about Island Windjammers

  • Who goes on Island Windjammers cruise ships?

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


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Island Windjammers Cruises


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Island Windjammers Cruise Tips, Activities, and Overview

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
  • Casual and social onboard atmosphere
  • Fares include drinks and snorkeling equipment

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

Island Windjammers Cruises Cruiser Reviews

Island Windjammers - As close to Paradise as I'll ever get!

It was easy to know ahead of time that the itinerary would be limited as many of the Caribbean Islands were still imposing severe traveling restrictions, however I just wanted to sail in the Caribbean and enjoy being spoiled by the wonderful crew on the ship .Fast forward 3 months to my next cruise, this time all the islands were open and the itineraries on both ships were pretty much back to normal with multiple islands visited - I won't list them as it is so much nicer to enjoy the surprise when the ops manager (on Vela) or the captain on Diamant give you a complete rundown (usually before dinner) of the itinerary for the following day.Read More
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10+ Cruises

Age 70s

Terrible management and no Covid SOP/Protocol

When the snorkelers came back on shore (by the grace of god no one got stung or stabbed) the decision was made to go stand in the shade of the abandoned bar (where crew told us we weren't allowed to stand) in an effort to get the attention of anyone on the ship to come 'rescue' us.Traveling with a company (IWJ) that says they have no SOP or protocol for when a passenger tests positive was not part of the calculation.Read More
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2-5 Cruises

Age 50s

Island Windjammer - Coming Back Strong After Covid

We discovered Island Windjammer in 2015; I'd been trying to persuade my wife to try a cruise for years - Barefoot Windjammer had long since gone - but she dug her heels in and resisted and resisted.Finally I wore her down and she agreed to try an Island Windjammer cruise on Sagitta on the the condition that if she didn't like it I was never to mention it again.Read More
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10+ Cruises

Age 70s

Wonderful experience

I felt this cruise offered something for everyone I couldn’t have asked for a better time.Far better than the big cruise liners of which I have been on several.Read More
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6-10 Cruises

Age 50s

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