Discover a More Intimate Caribbean

Snorkel spectacular underwater worlds or relax and sip a cocktail as you cruise the Caribbean. Unwind on the exquisite deserted beaches of Culebra or investigating hidden coves that only our small ships can reach. Wander through the rainforests of Montserrat, enjoy overnight stays in Virgin Gorda and St. Lucia and soak up the local flavor with a Private Event at Prickly Pear Beach, St. Lucia or Mayreau. For a limited time, Windstar will whisk you away on our Caribbean package with fares from $1,499 pp. 

SAVE UP TO 61%
BEST OF THE ABC ISLANDS Bridgetown to Orangestad 7 DAYS / FROM $2,199 PP This is the Caribbean for those with a taste for something a bit more exotic. The beaches establish a standard of beauty all their own. And between each eventful island, there is time to savor your surroundings - both on shore and on the deck of your elegant yacht.

SAVE UP TO 68%
JEWELS OF THE WINDWARD ISLANDS Bridgetown to Bridgetown 7 DAYS / FROM $1,599 PP This is the Caribbean of days gone by - deep blue waters, quiet coves, and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar.

SAVE UP TO 70%
YACHTSMAN'S CARIBBEAN Philipsburg to Philipsburg 7 DAYS / FROM $1,499 PP Let us take you into hidden coves and tiny harbors no one else can reach as you fully experience the Caribbean's private yachting scene. Sail to Virgin Gorda, with its assembly of house-sized rocks called The Baths. Savor the high life on St. Barts.

Why Windstar?   SECLUDED COVES
BIGGER CRUISE LINES CAN'T REACH  COMPLIMENTARY PRIVATE ISLAND EXPERIENCE  SNORKELING IN THE BEST OF THE CARIBBEAN'S UNDERWATER WORLD