Star Clippers Offers Two Free Hotel Nights on Select Caribbean Sailings

If the thought of winter fills you with existential dread and the sound of wind rustling through palm trees feels more like your natural habitat, then Star Clippers has just the ticket—or rather, the sail—for you. The tall-ship cruise line, known for vessels that look as if they’ve sailed straight out of a swashbuckling novel but with considerably more indoor plumbing, is offering a rather lovely winter incentive: two free hotel nights on select Caribbean voyages between November 2025 and March 2026.

Yes, free. As in, complimentary. As in, you could be lounging on a beach in St. Maarten with your feet buried in sand instead of trudging through slush in sensible waterproof boots. The catch? You must book before September 30, 2025. But that gives you plenty of time to procrastinate before leaping into action at the last minute.

Travelers can use the bonus nights to gently recover from long flights, take in some early island ambience, or simply refuse to leave paradise without a fight. The pre- or post-cruise stays include breakfast and a transfer to your majestic sailing ship—presumably not by rowboat—and take place in a range of perfectly postcard-worthy locations.

For sailings around the "Leeward Islands" or "Treasure Islands," guests stay at the Holland House Beach Hotel in Philipsburg, St. Maarten—a charming spot right on the water and conveniently close to rum punch. Those exploring the "Windward Islands" or "Grenadine Islands" itineraries will spend their land-based nights at the Hotel Courtyard Barbados in the bustling village of Hastings, which is considerably more laid-back than its name suggests. And for the more ambitious 11-night journey from Jamaica to Antigua, the Deja Resort in Montego Bay’s Hip Strip (a name that somehow manages to sound both exciting and like a minor injury) will host weary travelers before they board.

These itineraries aren’t your run-of-the-mill mega-cruise routes. Star Clippers takes a more intimate approach, weaving through lesser-known islands like Iles de Saintes, Dominica, Guadeloupe, and Bequia—places where goats outnumber rental cars and the local bakery might also sell hardware supplies, just in case. Prices begin at a respectable $1,970 for seven-night voyages and go up depending on how much paradise you're after.

The pièce de résistance is the 11-night voyage from Jamaica to Antigua, sailing the storied Sir Francis Drake Channel. Ports of call include a grab-bag of nautical poetry: Tortola’s Sopers Hole, Virgin Gorda, Jost Van Dyke, and a few places where you half expect to see Jack Sparrow ordering a drink. Fares start at $3,090, and the sea views come standard.

Star Clippers itself is a bit of a marvel. The company operates three of the largest sailing ships in the world, complete with modern amenities, polished teak decks, and the sort of sails that make you instinctively want to shout “Ahoy!” Star Flyer and Star Clipper carry 160 guests each, while the Royal Clipper—officially the world’s largest fully-rigged sailing ship—accommodates 227 people and at least one person who will always be quoting nautical trivia.

In short, if you’re after a cruise with actual sails, proper sea breezes, and the smug satisfaction of telling people you spent January hopping between Caribbean islands instead of digging your car out of a snowdrift, this might just be your moment.