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Caribbean Cruises

Hidden Harbors. Private Beaches.
Island-Hopping in Private Yacht Style.

Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These are the siren songs that lure anyone with a yacht and a yearning to escape to the incomparable Caribbean Islands. Whether you’re cruising through turquoise waters or lazing on powdery white beaches, the glamorous harbors and unknown coves of this area remain a hidden treasure.


Philipsburg to Philipsburg - 9 Days

From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Here’s the best of the Caribbean in one single voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.

Complimentary Destination Discovery Event • St. Lucia: Island Experience

Bridgetown to Oranjestad - 9 Days

This is the Caribbean for those with a taste for something a bit more exotic. Colonial influences are still going strong here, from the “Little England” island of Barbados to still-very-Dutch Aruba, Bonaire, and Curaçao. Days ashore promise unexpected discoveries – a donkey sanctuary on Bonaire, underground rivers and caves in Barbados, a chocolate factory on Grenada, an artist colony on Curaçao. Beaches seem to shrug off the challenge of more northerly islands as they establish a standard of beauty all their own, swept by steady gust-free trade winds that make learning to windsurf a breeze. And between each eventful island, there is time to savor your surroundings – both on shore and on the decks of your elegant yacht.

Complimentary Destination Discovery Event • Mayreau: Island Experience

Bridgetown to Bridgetown - 7 Days

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. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.

Complimentary Destination Discovery Event • Mayreau: Island Experience

San Juan to San Juan - 7 Days

Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. Then explore Puerto Rico’s best-kept secret: the island of Culebra. It’s a natural paradise, home to one of the oldest bird sanctuaries in the United States and to Playa Flamenco, rated the third-best beach in the world. As you continue on this bewitching cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you. Skip more common and commercial ports like St. Thomas and Philipsburg in favor of less-visited destinations like Marigot and Montserrat. Bypass the major cruise terminals in favor of exclusive marinas and anchorages. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.   

Complimentary Destination Discovery Event • Prickly Pear Beach: Island Experience

Philipsburg to Philipsburg - 7 Days

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. Explore the quaint island charm of Soper’s Hole and the inviting beaches of Jost Van Dyke as you overnight in the harbor. Sail to Virgin Gorda, with its assembly of house-sized rocks called The Baths. Savor the high life on St. Barts.

Complimentary Destination Discovery Event • Prickly Pear Beach: Island Experience

San Juan to Bridgetown - 7 Days

Spend pampered days and nights in the secret hideaways of the Caribbean, kayaking off the Watersports Platform, walking on uncrowded beaches, and admiring sunsets reserved just for you. Linger on smaller islands where sea turtles nest and smiles are genuine. Learn how to say “amazing place” in Creole. Let nature and the Windstar staff fulfill every dream you’ve ever had about paradise.

Complimentary Destination Discovery Event • St. Lucia: Island Experience

Oranjestad to Colón - 7 Days

Discover the “deep south” of the Caribbean, beyond the mainstream cruises. The Dutch ABC islands acclaimed for their crystalline waters and world-class beaches, diving, and snorkeling. Seldom-visited mainland ports with a lively Caribbean vibe. And towns founded on Spanish gold that retain their colonial charm all these centuries later. It’s a voyage of discovery you won’t want to miss.

Complimentary Destination Discovery Event • Curacao: An Antillean Experience

Philipsburg to Philipsburg - 15 Days

Here’s a unique way to spend the holidays that will leave you with delightful memories and a stress-free holiday break. The Grand Caribbean Holiday cruise will take you round trip from St. Maarten to 11 unique islands over the course of 16 days. From the stunning UNESCO site of the twin Pitons to the quaint island charm of Soper’s Hole and Roseau. From the dazzling white sand beaches to the mesmerizing waters in shades of peacocks and mermaids, this holiday vacation will leave you equally at home in exotic harbors and hidden coves. Relaxed, relieved, refreshed, you’ve just found a new way to celebrate the season.

Complimentary Destination Discovery Events • St. Lucia & Prickly Pear Beach (Virgin Gorda) Island Experiences

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