Windstar Caribbean Cruises, 2024, 2025 and 2026 Caribbean Windstar Cruises | The Cruise Web

Windstar Cruises Caribbean Cruises

Windstar Cruises to the Caribbean islands offer a relaxing escape to some of the world’s most beautiful turquoise waters and white beaches. Plus, thanks to Windstar Cruises’ unique small-ship cruising experience, you’ll visit ports that aren’t included in the itineraries of many more traditional cruise lines. These unique ports may include Soper’s Hole, Tortola, BVI; Jost Van Dyke, Great Harbour, BVI; Gustavia, St Barts; Pigeon Island, St. Lucia; or Mayreau and Bequia in St Vincent and the Grenadines. Less visited islands means less crowded destinations and a more relaxing experience. Windstar Cruises’ guests choose the Caribbean for a variety of reasons, including its vibrant cultures, fascinating history, much sought-after adventure spots, world-renowned beaches and more. No matter what pulls you to the Caribbean, when Windstar Cruises brings you there, the experience is unforgettable.


Things to Do on a Caribbean Cruise with Windstar Cruises


Vacationing in the Caribbean with Windstar Cruises is an opportunity to explore hidden islands and tropical treasures, such as those found around the islands of St. Lucia, Grenada, Barbados, Dominica, Guadeloupe and more. You can get up close and personal with exotic wildlife, learn about the region’s past at the historic fortresses, snorkel through coral reefs or relax in a hot spring. Featured below are a few of our favorite things to do when cruising through the Caribbean with Windstar Cruises:



Windstar Cruises black sand beach Dominica Caribbean islands
  • Champagne Reef Snorkel Adventure (Roseau, Dominica)
    Head to Dominica’s top snorkeling site for a 2-hour experience with the diverse marine life of Champagne Reef – so named for the bubbles that rise out of the volcanic vents beneath the sea floor. While you float through the bubbles, colorful fish will dart in and out of the various coral formations.


Windstar Cruises beach at Pigeon Island Saint Lucia caribbean
  • Getaway in Paradise (Pigeon Island, St. Lucia)
    St. Lucia’s precious Pigeon Island is the hot spot for Windstar’s private beach party, complete with steel drums, an open bar and fun, fun, fun! Mingle with fellow guests while enjoying fresh fish, conch and more. While you wait for the food to be prepared, try your hand at any number of beach or watersports activities, including snorkeling, volleyball, horseshoes, bocce ball and much more.


Windstar Cruises Guadeloupe Lesser Antilles view from Le Gosier over Dupuy Bay
  • Clear Bottom Kayaking (Les Saintes, Guadeloupe)
    One of the best ways to explore the calm waters of the Caribbean is aboard a two-person clear bottom kayak. Your tandem ride features its very own window to the sea, and all you have to do is look down. Guides will inform you about the culture, history and geology of the islands.


Windstar Cruises view of the port of Basseterre in St. Kitts West Indies
  • Sky Safari Zipline Adventure (Basseterre, St. Kitts)
    Take a breathtaking ride above Basseterre with a zip line adventure for the ages! Journey up the Valley of the Giants where you’ll strap in and zip across a mile of lines for a new perspective of the Caribbean – hands- and feet-free like a bird through the canopy.


Windstar Cruises scuba diver shooting picture of barrel sponge
  • Certified Scuba Diving (Nevis, St. Kitts and Nevis)
    An expert dive instructor will take you to one of Nevis’ premier dive sites, such as Nag’s Head, Monkey Shoals or Devil’s Caves, where you’ll spend hours exploring the island’s underwater realms. You’ll watch various sea creatures navigate the coral reefs while you do the same.


Windstar Cruises scenic view of St. Maarten dutch side in the Caribbean
  • America’s Cup Sailboat Racing (Philipsburg, St. Maarten)
    Harness the cool breezes of St. Maarten on a sailboat race aboard a multi-million dollar America’s Cup sailboat. You’ll be assigned to one of three boats where the crew will provide a brief training before sails go up and the race is on. During the race, you can either relax and enjoy onboard refreshments or take a crew member’s position and help bring your team to victory.


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