Windstar Cruises

Star Collector: Lovely Leewards

Whether you’re passionate about swimming among rarely seen undersea wildlife or the intricate cultures and intertwined European histories of the Windward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands normally associated with places like Madison Avenue, but displayed in an ambiance that’s anything but intimidating. Stare in wonder at the glow from miniscule bioluminescent organisms stirred by your kayak paddle during a tour of the Fajardo Bio Bay nature reserve near San Juan. Master the art of cooking with distinct spices like nutmeg, cloves, and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg. This Caribbean getaway is the perfect duration for lovers of island life and those who want to spend more time exploring the Windward Islands overlooked by other cruise lines.

04/02/2023 through 11/18/2024
04/02/2023 through 12/07/2024

Day 1 San Juan, Puerto Rico
Day 2 At Sea
Day 3 St. GeorgeS, Grenada, Grenada

Arrive Time: 9:00 AM – Depart Time: 10:00 PM
Day 4 Bequia, Saint Vincent And The Grenadines

Arrive Time: 8:00 AM – Depart Time: 10:00 PM
Day 5 Pigeon Island, St. Lucia, Saint Lucia

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 6 Les Saintes, Guadeloupe, Guadeloupe

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 7 Philipsburg, St. Maarten, Saint Maarten

Arrive Time: 8:00 AM – Depart Time: 2:00 PM
Day 8 San Juan, Puerto Rico

Arrive Time: 7:00 AM – Depart Time: 11:59 PM
Day 9 Charlotte Amalie, St Thomas, United States Virgin Islands

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

Arrive Time: 9:00 AM – Depart Time: 10:00 PM
Day 11 Little Bay, Montserrat, Montserrat

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 12 Philipsburg, St. Maarten, Saint Maarten

Arrive Time: 7:00 AM – Depart Time: 10:00 PM
Day 13 Great Harbour, Jost Van Dyke, British Virgin Islands

Arrive Time: 8:00 AM – Depart Time: 11:59 PM
Day 14 Virgin Gorda, Bvi, British Virgin Islands

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 15 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.

11/09/24 - 11/23/24

Starting At $5,099

Room Options
  • Suite$5099.00
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11/23/24 - 12/07/24

Starting At $5,099

Room Options
  • Suite$5099.00
Get A Quote
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