Windstar Cruises

San Juan & the Virgin Islands

Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean 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 in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of exclusive marinas and anchorages on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant ship is already there.

04/02/2023 through 11/25/2024
04/02/2023 through 12/07/2024

Day 1 San Juan, Puerto Rico
Day 2 Charlotte Amalie, St Thomas, United States Virgin Islands

Arrive Time: 8:00 AM – Depart Time: 10:00 PM
Day 3 Gustavia, St. Barthelemy, St. Barthelemy

Arrive Time: 9:00 AM – Depart Time: 10:00 PM
Day 4 Little Bay, Montserrat, Montserrat

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 5 Philipsburg, St. Maarten, Saint Maarten

Arrive Time: 7:00 AM – Depart Time: 10:00 PM
Day 6 Great Harbour, Jost Van Dyke, British Virgin Islands

Arrive Time: 8:00 AM – Depart Time: 11:59 PM
Day 7 Virgin Gorda, Bvi, British Virgin Islands

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 8 San Juan, Puerto Rico

St. Martin

Thirty seven sandy beaches, sparkling Caribbean seas, soothing trade winds, fine dining and incredible duty free shopping combine to make St.Martin/St.Maarten a true vacationers paradise.

Destination St. Martin is proud to represent a number of smaller hotels on the French side of the island; generally not the type of places found in the glossy tourist brochures but rather more intimate yet immaculate properties which allow the visitor to experience true island life. Accommodations are available on the beach in the beautiful French village of Grand Case, in Nettle Bay near the town of Marigot and at popular Orient Beach.

The smallest island in the world ever to have been partitioned between two different nations, St. Martin/St. Maarten has been shared by the French and the Dutch in a spirit of neighborly cooperation and mutual friendship for almost 350 years.

The border is almost imperceptible and people cross back and forth without ever realizing they are entering a new country. The only marker is a monument between Union Road and Bellevue, testifying to centuries of peaceful cohabitation and the treaty that made the arrangement possible.

All the same, each side has managed to retain much of the distinctiveness of its own national culture. The French tend to emphasize comfort and elegance. The beaches are secluded, the luxury resorts provide lavish accommodations, and the restaurants offer some of the finest dining experiences anywhere in the Caribbean. The latest French fashions can be found in many of the shops, and the smell of fresh croissants and pastries mixes everywhere with the spicy aromas of West Indian cooking. Small caf’e9s and charming bistros add a decidedly Gaelic and cosmopolitan flair to the place. On the whole the atmosphere remains very relaxed.

11/16/24 - 11/23/24

Starting At $3,199

Room Options
  • Suite$3199.00
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11/30/24 - 12/07/24

Starting At $3,199

Room Options
  • Suite$3199.00
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