ISLAND WINDJAMMERS

Remember Windjammer Barefoot Cruises? Enormously popular in the ‘80s and ‘90s for its ultra-casual, rum-fueled Caribbean sailing adventures, the line folded in 2008, leaving thousands of loyal passengers sad and landlocked. Enter Island Windjammers.

Launched in 2009 by and for Windjammer Barefoot regulars when they got together to buy the 101-foot brigantine schooner Diamant, the line is a more mature version of its barefoot predecessor, operating truly intimate sailing adventures that tootle around the quieter corners of the Caribbean, far from the megaship mega-crowds.

Sure, there’s still plenty of rum punch and Red Stripes consumed, but the volume of the party has been turned way down to just the perfect level. (Island Windjammers is not to be confused with Sail Windjammer, a now defunct one-ship line that used to operate the 72-pax Mandalay, formerly of the Windjammer Barefoot Cruises fleet.)

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Diamant in all her glory. * Photo: Island Windjammers

Fleet

Diamant (built 1978 & 10 passengers) – Windward Islands, Caribbean

Vela (b. 1988 & 26 p) – British Virgin Islands, French West Indies & Leeward Islands, Caribbean

Note: the 24-passenger 1960-built Sagitta is no longer a part of the Island Windjammers fleet.

Island Windjammers has started offering yacht charters in Europe; they did Croatia in 2023 and in 2024, it’s the Greek Isles aboard the 8-pax Lyra doing 10-night itineraries. More info HERE.

Island Windjammers Passenger Profile

Young-at-heart mostly American couples, singles and groups of friends 45+ who crave a carefree Caribbean getaway with zero pretension.

Summers and holiday weeks see occasional families with children; though the minimum age is 8 and it’s probably better for kids to be at least 10 or 12+.

Note: Island Windjammer’s ships are not accessible for people with restricted mobility, as staircases are steep, doorways narrow and door sills high.

Price

$ Moderate

Included Features

All on-board meals
Locally brewed beer, wine & rum punch*
Soft drinks & juice
Use of ship’s snorkel gear
Port taxes & government fees

*You’re also invited to bring along your own booze and the ships provide the mixers (there is no cash bar on board). Internet is not available, and some island locations will have to make do.

The fleet calls on great little places like Tobago Cays. * Photo: Island Windjammers

Island Windjammers Itineraries – Cruises Year-Round

6- and 12-night Leeward Island cruises round-trip from St Martin or St. Lucia, calling on some combination of Anguilla, Antigua, Dominica (Portsmouth & Roseau), Guadeloupe, Iles des Saintes, Martinique, Montserrat, Nevis, St. Barths, St. Eustatius, St. Kitts, St. Lucia and Tintamarre

6-, 9- and 12-night Windward Island cruises round-trip from Grenada or St. Lucia, calling on some combination of Bequia, Canouan, Carriacou (Tyrell Bay & Hillsborough), Grenada, Mayreau, Mustique, Petit St. Vincent, Sandy Island, St. Lucia, St Vincent, Tobago Cays, Union Island and Young Island

6- and 12-night British Virgin Islands (BVIs) & Leeward Island cruises round-trip from St. Martin or Tortola, visiting some combination of Anguilla, Jost Van Dyke, Nevis, Norman Island, Salt Island, St. Barths, St. Kitts, St. Maarten, Tortola or Virgin Gorda

6- and 12-night French West Indies cruises round-trip out of St. Lucia, visiting some combo of Dominica (Portsmouth & Roseau), Guadeloupe, Iles des Saintes, Martinique and St. Lucia

Sample Itinerary

In the British Virgin Islands, most 6-night cruises embark at Road Town on Tortola.

A typical round-trip itinerary will include calls at Cooper Island, Jost Van Dyke, Norman Islands and Virgin Gorda.

Each day is more gorgeous than the last. * Photo: Island Windjammers

Why Go?

To let your hair down, work on your tan and hang out with like-minded others who operate on island time.

When to Go?

All year around, though remember hurricane season in the Caribbean is officially June through November.

Activities & Entertainment

The day starts with the captain’s story time when he explains what’s happening for the day; the ships spend part of every day in port somewhere. The pace is easy going and free — while away the day swimming off the side of the ship (when conditions permit), take the ships’ kayaks for a spin nearby, try paddle boarding, or sip rum punch with new friends in an inflatable “floating island.”

There are a handful of shore excursions offered on most itineraries, but many passengers are content to find a good beach or wander around on their own. Sometimes lunch is served on a quiet beach somewhere, otherwise meals on are on board.

Occasionally passengers will arrange their own diving trips, and spend part of a day deep down under looking at the colorful fishies.

Happy hour is a big thing and drinks on deck are a favored pastime for many; you’re free to bring aboard your favorite spirits or mixers, though why bother when beer, wine, rum punch and soft drinks are on the house.

Evenings, the crew may start a bonfire on a nearby beach or organize a pub-crawl.

Theme cruises from time to time focus on rum (with a rum expert on board to educate and do tastings), solo cruisers (no kids or couples allowed!), pirates (with costume contests, pirate trivia and visits to spots where Pirates of the Caribbean was filmed), local food tasting, and yoga. Om shanti! 🙏🏼

Swing from the rigging, yipeee! * Photo: Island Windjammers

Dining

Meals are served at one very social open seating at a few tables, with local dishes to the tune of chicken roti, conch soup, pumpkin soup, callaloo and fresh fish as well as continental standards the likes of cheeseburgers and salads.

Fresh island fruits are part of the picture, from passion fruit to guava, star fruit, sour oranges and bananas.

Vegetarian and Gluten Free diets are catered for but not Kosher nor Vegan.

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Ships

The whole point of an Island Windjammer cruise is to be outside on deck soaking up the sun and fresh Caribbean air, and enjoying the sailing ship experience and the quirkiness of the vessels — each has a very interesting background. — Heidi Sarna

Diamant

The 10-passenger Diamant was built in 1978 in Taiwan and then later spent two decades sailing in the Galapagos Islands before Island Windjammers purchased her in 2009. She’s been the fleet favorite ever since.

She got a facelift in fall 2016 that reduced her capacity to 10 passengers in five cabins and created an overall spiffier look (“sophisticated not stuffy” the line’s website points out).

Of the two passenger decks, the top deck has both covered and open-air dining tables, plus a bar and deck chairs. The cabins are on the lower deck; there’s no elevator

Diamant sports four cabins with double beds below and single bunk above, and with full bathrooms with separate showers; and a fifth cabin is a suite with a queen bed, sitting area and a full bathroom.

Small as you’d expect on sailing ships, but charming, wood-paneled and the perfect cozy nests to catch up your beauty rest; otherwise, life is lived up on deck or on shore.

All cabins have 110v outlets, blow dryers, shampoo/soap, portholes and private bathrooms with separate shower stall.

A cozy and very nautical Diamant cabin. * Photo: Island Windjammers

Vela

The 26-passenger Vela was built in 1988 in Puget Sound, Washington, and deployed in the Marshall Islands as a floating medical clinic called Tole Mour, or “Gift of Life and Health.” Later she was used as an education vessel for students studying sailing, oceanography and marine biology.

In late 2014, Island Windjammers purchased the ship and rechristened her Vela, and a year later did major renovations, replacing the dormitory-style cabins with en suite single and double cabins; there’s also a new pilot house, large enclosed bar and dining saloon on the top deck.

Vela’s cabins include two tiny Cadet Cabins with raised small double beds (for one or two people) each with a private all-in-one bathroom (no separate shower stall).

There are a pair of Solo Cabins, one with a porthole and one without, that share one bathroom with a separate shower stall (each cabin can accommodate one or two people).

The two Standard Cabins are a bit larger with a double lower bed and a single bunk above, while six Deluxe Cabins have a larger double bed with single bunk above.

A pair of Compass Cabins at the aft of the ship has a queen size bed (and no upper bunk) and the one and only Topsail Cabin has a queen bed and larger bathroom.

Finally, the relatively spacious Owner’s Suite has a king size bed, mini-fridges, and a large bathroom — both cabin and bathroom have portholes.

All cabins have 110v outlets, blow dryers, shampoo/soap, portholes, and all but two solo rooms, cabins have private bathrooms with showers.

Vela’s Owner’s Suite, not too shabby! * Photo: Island Windjammers

Along the Same Lines

Star Clippers is in the ballpark, though its passengers are more international and its ships are much larger, and the overall experience is more high-end. The Maine Windjammers — one of which is reviewed on QuirkyCruise.com, the J&E Riggin — have a similar vibe, though the Island Windjammers’ ships offer more of a “cruise” experience with more amenities.