ESCAPE. EXPLORE. EXHALE
MOST POPULAR
VELA
FROM: $2325
Vela is one of the most recognizable and loved tall ships to sail the Caribbean. This is your last chance to experience our Island Girl as you remember her. She’ll be back after a well-deserved refit, but in the meanwhile, take one last rope swing to freedom and give her a Velacolada cheers, for a cruise to remember!
26 GUESTS
6 & 12 NIGHTS
FIND YOUR NEXT ESCAPE
WHY CRUISE WITH ISLAND WINDJAMMERS?
Small Ships, Big Adventures
Experience the magic of sailing on intimate ships where every voyage feels personal, not crowded.
Relaxed Travel, Remote Escapes
Our small ships slip into hidden harbors and iconic small islands that the big cruise liners can’t reach, letting you experience the Caribbean and Mediterranean the way they were meant to be: up close, authentic, and wonderfully laid-back.
Stress-free, All-Inclusive Cruising
Enjoy transparent pricing, freshly prepared meals, and friendly service with no hidden extras.
Trusted Since 2009
Proudly independent and sailor-founded, we’ve been delivering unforgettable small ship adventures since our very first cruise.
A Welcoming Sailing Community
Beginning with your first voyage, you’re not just a guest—you’re part of the Island Windjammers community. Board as strangers. Leave as friends.
THE SPIRIT BEHIND EVERY VOYAGE
ESCAPE.
Set Sail Your Way
Leave the crowds and chaos behind and rediscover the freedom of the open sea. With Island Windjammers small ship cruises, you’ll experience the Caribbean, Croatia, and Greece intimately, authentically, and under sail. Our fleet offers something for every kind of cruiser. Choose from schooners with old-world charm, to sleek luxury yachts, and even our brand-new zero-emissions sailing ship. We call our growing fleet the Island Girls and each one has her own personality, with a shared spirit of relaxed adventure, genuine connection, and the pure joy of life under sail.
EXPLORE.
Hidden Escapes & Iconic Shores
Our small ship cruises reveal secluded anchorages, vibrant local communities, and hidden gems throughout the Leeward and Windward Islands, the French West Indies, the British Virgin Islands, the Turks & Caicos, Croatia, and Greece. Whether you’re snorkeling in turquoise Caribbean coves or strolling sun-soaked Mediterranean harbors, every voyage is an unforgettable story waiting to be lived.
EXHALE.
Relax, You’re Among Friends
Since 2009, Island Windjammers has been the trusted choice for travelers seeking authentic, all-inclusive small ship cruising with a personal touch. We warmly welcome solo travelers, couples, friends, and groups sailing together. We’re one of few operators with designated cabins for solo sailors. Transparent pricing, friendly crew, and a laid-back atmosphere mean that you can truly unwind. With our Love For Sail Rewards Program, your loyalty starts paying off from your very first voyage. Step aboard, breathe deeply, and join a tight-knit community of sailors who’ve found their home at sea.