Frommers | Island Windjammers

Remember Windjammer Barefoot Cruises? A decade ago, they were the self-styled pirates of the cruise business, with weeklong (and longer) cruises on a fleet of old-fashioned tall ships, plus one shady-looking cargo/passenger vessel that kept them all supplied. The vessels prowled the Caribbean like privateers, scooping up passengers at different island ports and taking off on itineraries that were only kinda-sorta thought out ahead of time. The line lived on the edge, keeping its ships just about legal and its crews just about paid while accumulating a loyal cohort of repeat guests drawn by its outsider image and promise of unstructured, few-holds-barred fun. And it was fun — terrific fun, and we miss it, because in 2007 the line finally fell off the ethical and financial tightrope it’d been walking, and collapsed with a reverberating kaboom.

Flash forward to 2009, and all those Windjammer fans — some of whom sailed with the line dozens of times, year after year — were still out there, many still saddened that no similar cruise operation had sprung up to take Windjammer’s place. Enter Island Windjammers, a start-up created by former crew and passengers of Windjammer Barefoot. In November 2009, the line began offering weekly 6-night cruises from Grenada aboard the 101-foot, 12-passenger brigantine schooner Diamant. Everything old is new again! If a bit more mature and less, shall we say, illegal. Though the line is starting small, it hopes to add larger ships as it matures. We wish them good luck, because the Caribbean cruise biz desperately needs this kind of small, casual option to balance out the megaship bigwigs.

Diamant was built in 1978 and is more akin to the small windjammers that sail the Maine coast than to the big vessels of Windjammer Barefoot. The vessel is tight and simple, with six air-conditioned cabins with portholes and private bathrooms, a combo lounge/dining room, an outdoor dining area, and lots of open deck space. Oh, and there’s this: She’s gorgeous, with a beautiful profile, lovely detailing, and shiny woodwork throughout. Cruises sail among the Grenadine Islands (an absolutely ideal locale for this type of ship), visiting Carriacou, Mayreau, Tobago Cays, Union Island, Palm Island, and Bequia. Though the line consciously tries to emulate the ultracasual Windjammer Barefoot vibe and does whip up the iconic rum swizzles in the evening, it shies away from the heavy drinking and risqué party atmosphere that sometimes sent Windjammer ships over the edge.

Rates for Diamant‘s cruises start at $1,599 per person (or $265 per day), including all meals, beer, wine, soft drinks, port taxes, and crew gratuities.

Diamant sails the Eastern Caribbean/Grenadines from Grenada (year-round).