Looking for a sailing vacation guided by the sun, moon, and tides? You've found it!

Island Windjammers has been offering unforgettable small-ship cruises since 2009. Our sailing ships explore the Caribbean, Greece, and Croatia. Our carefully curated itineraries deliver an authentic, intimate island-hopping experience, far from the crowds and close to adventure.

With guest capacities ranging from just 8 to 32, our ships can explore hidden destinations that the big cruise liners simply can’t reach. Whether you're dreaming of a romantic getaway, a family adventure, a private group sail, or a solo escape, we have the perfect vessel for you. Sail aboard our classic clipper ship Vela, our timeless schooner Diamant, our premium sailing yacht Lyra, or experience the future of eco-luxury on our new zero-emission ship Leda. Joining the fleet from Winter 2026 is Klara, a luxury three-masted schooner, ready to turn heads and sail the trade winds.

This is small-ship cruising at its finest: authentic, personal, and unforgettable.

Our Island Girls are fully-crewed and feature air-conditioned cabins, private bathrooms, portholes, and all modern comforts.

Your Captain sets the course. Each day is a new adventure. Free your mind from schedules, and savor each moment as the crew hoists the sails, the trade winds fill the canvas, and you set off to your next secret island destination.

There’s no rush. You’ll have plenty of time ashore to explore vibrant villages, sip rum at quirky beach bars, or laze the days away on pristine beaches.

Even the nights are magical. Shipmates gather on deck to dance, share a joke or tell tales of the day’s adventures. Lean on the rail, and steal a kiss under a canopy of stars.

Live in the now, and breathe it all in. This is island life--and you’re living it!