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Windstar Cruises takes you where larger cruise lines can't, giving you an intimate experience of places like the Caribbean.

Recharge in the Caribbean with Windstar Cruises

One week in the Caribbean on the Yachtsman's Caribbean cruise by Windstar Cruises pairs unrivaled intimacy with spectacular excursions as you get an unprecedented look at the region over the course of eight days. When you depart Philipsburg, St. Maarten aboard the Wind Surf, you'll set sail toward six different ports that allow you to enjoy some of the world's best beaches without the noise of thousands of tourists in one place at the same time.

Here are some of the highlights that will give you an experience as refreshing as the crisp, blue waters surrounding you on this cruise.

St. Maarten

Before you even set sail on your Caribbean voyage, you'll find it hard to avoid the shops and brightly-colored buildings in St. Maarten. You'll fall in love with the Caribbean right away with the Philipsburg port's local restaurants, photography opportunities, and jewelry and fashion stores. You'll also return to this location at the end of the cruise, so if your schedule doesn't allow you any time at the beginning, you'll still have a chance to buy some souvenirs that commemorate all the experiences you enjoyed during the week.

Gustavia/St. Barts

Although St. Barts could easily be described as an adventure port, this first stop after St. Maarten also has plenty of shops to browse, and beaches and marinas basking under the warm Caribbean sun. You can tour the island in a small vehicle with up to 6 people, or you can head out to Colombier Bay for some sunbathing and reading, thanks to a full crew who will take care of the sailing and serving you drinks.


When you get to Anguilla, try piloting your own Zodiac and explore the open water. This 2-person watercraft will allow you to find several secret beaches that can't be reached by road or seen on a map. This is a perfect chance to find some secluded sand and disappear for a day.

A significant amount of time could also be spent at Da Vida, which translates to "gives life" in Spanish. This is a five-hour excursion that will put a tropical drink in your hands on a beach in Crocus Bay. After soothing your mind by the water, your relaxing day will culminate with one of the best meals you can find on the island at the aptly named Bayside Grill.


Road Town on the island of Tortola is the capital of the British Virgin Islands, and it could easily be known as the shopping capital of the area too. Before collecting bags of souvenirs, take a stroll on Main Street, home of historical landmarks like St. George's Anglican Church, Britannic Hall, and the Folk Museum. Waterfront Drive (located right along the edge of the island, as you might have guessed) will lead you to the Old Government House Museum and several restaurant options to enjoy a scenic meal.

If you're looking for a little bit more action, this port offers snorkeling at the uninhabited Norman Island. You might find more than fish during this excursion, as pirate treasure is known to have been buried at the Caves at Treasure Point. If you'd like to stay above ground, Tortola offers a scenic drive to Cane Garden Bay where you can swim or lay on the white-sand beach there with a complimentary drink. Along your way home, you'll also stop at the Callwoods Rum Distillery and the Sir Francis Drake Channel.

Antigua/Falmouth Harbor

The final stop before St. Maarten is brimming with activities as well, but if you're looking for a calm conclusion to your vacation, there are plenty of beaches to enjoy. Some people say the island has 365 beaches, one for each day of the year. Grab a towel, some sunscreen, and a book, and you're set for the day. An Antigua island tour is a great option if you'd like a ride to places like the Blockhouse Ruins on top of a sheer cliff 450 feet above the Atlantic Ocean. The view there will rival another you'll see on this tour at Shirley Heights, about 500 feet above sea level overlooking the Atlantic and English Harbor.

Find a full itinerary of the Yachtsman's Caribbean cruise by visiting

You can book your next vacation aboard the Yachtsman's Caribbean cruise here, or test your luck at winning a trip for two on the Yachtsman's Caribbean cruise by visiting this link.