Windstar Cruises Caribbean: 7 nights from Philipsburg with Wind Surf
Jan 11, 2026
Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Saint Vincent and the Grenadines, Barbados
Cruise itinerary
Departure Port: Philipsburg ➞
Landing: Bridgetown
-
Sunday, January 11, 2026 - 7:00 PMPhilipsburg
-
Monday, January 12, 2026 8:00 AM - 9:00 PMBasseterre
-
Tuesday, January 13, 2026 8:00 AM - 10:00 PMGustavia
-
Wednesday, January 14, 2026 8:00 AM - 10:00 PMSaint Johns
-
Thursday, January 15, 2026 8:00 AM - 1:00 PMLes Saintes
-
Friday, January 16, 2026 8:00 AM - 5:00 PMMayreau
-
Saturday, January 17, 2026 7:00 AM - 2:00 PMKingstown
-
Sunday, January 18, 2026 5:00 AM 11:59 PMBridgetown

Philipsburg
Philipsburg is the capital of Saint Maarten on the Caribbean Seathis city is one of the best cruise ports in the Caribbean, famous for shopping.
Philipsburg is the capital of the Dutch side of St.Marteen, a Caribbean island divided in Dutch and French territories (Saint Martin).
Business seekers flock to the duty-free shops and tax-free sales along the long commercial district of Philipsburg. Visitors can also enjoy art galleries in the city, historic forts, casinos and a zoo, as well as Great Bay Beach and the promenade.

Basseterre

Gustavia

Saint Johns
Fascinating History of Saint Johns in Antigua and BarbudaSaint Johns, located in Antigua and Barbuda, has a captivating history that dates back to the colonial era. Founded by the British in the 17th century, the city played a significant role as a strategic port in the Caribbean Sea. Over the centuries, Saint Johns has evolved into a vibrant cultural and tourist hub, preserving traces of its colonial past in its architecture and traditions.
Tropical Climate and Sunny DaysSaint Johns enjoys a tropical climate with warm temperatures and plenty of sunshine throughout the year. Summers are hot and humid, perfect for lounging on the white sandy beaches and swimming in the crystal-clear waters of the island. Winters are mild and dry, providing optimal conditions for exploring the city and its attractions without being hindered by rainfall.
Top Attractions and Places to Explore in Saint JohnsSaint Johns offers a plethora of attractions that cater to all interests. The historic Nelson's Dockyard, a UNESCO World Heritage Site, showcases naval history and stunning views of English Harbour. The colorful markets of Redcliffe Quay are ideal for shopping for local crafts and souvenirs. Don't miss out on visiting Shirley Heights for panoramic vistas and lively sunset parties.
Local Cuisine: Authentic Flavors of Antigua and BarbudaThe culinary scene in Saint Johns reflects the rich gastronomic heritage of Antigua and Barbuda with dishes that tantalize the taste buds. Indulge in seafood delights like grilled lobster, spicy pepperpot stew, and sweet potato pudding. Sample local delicacies such as saltfish with fungee (cornmeal dish) and savor rum punch or Wadadli beer for a true taste of the islands.
Embark on an Unforgettable Cruise from Saint JohnsTo enhance your visit to Saint Johns in Antigua and Barbuda, consider booking a cruise departing from this picturesque city. Cruises around the surrounding islands offer breathtaking views of the turquoise Caribbean waters, pristine beaches, and vibrant coral reefs. Booking a cruise from Saint Johns guarantees unforgettable experiences and a deeper connection to the natural beauty of the Caribbean islands.

Les Saintes

Mayreau

Kingstown
Kingstown is the capital of Saint Vincent and Grenadine, an insular state of Central America. Thanks to its strategic port, the city has developed its commerce and has become the economic center of the country. Kingstown is known worldwide as the 'city of arches' because of the large number of arches in the achitecture of the buildings and monuments scattered around the city.
Its location, between the coast of the Caribbean and the hills, offers the opportunity to take part in many activities. For sea lovers, the beautiful beaches offer the opportunity to relax while tasting fresh drinks. For sport lovers, there is the opportunity to do water activites that allow you to live this unique experience and immerse yourself in the surrounding areas. For those who enjoy long walks and breathtaking city views, venturing into the city hills is the best choice for you!
In particular there are two forts, Fort Charlotte and Fort Duvernette, once used as crucial points for the defense of the city, today they are panoramic points that will leave you speechless! One of the best ways to reach Kingstown is aborad a cruise ship. Choose a cruise that depart from Kingstown or that has the city as a stop is the best choice for those who want to discover the beauties of this city and enjoy this unique natural spectacle also during navigation.

Bridgetown
Bridgetown, an island located in the eastern part of the archipelago, is the capital of Barbodos islands. It is renowned for its duty-free shops and its cultural and historical attractions.
It is one of the most oldiest cities of the Carribean Islands; its architecture full of colonial buildings blending with warehouses and brash modern office blocks fascinates and entertains visitors. The center of the city is the Carenaggio, a tourist port that confines with the Parliament of Barbados (where are located two small fashinated history museums). Some of the most famous religious buildings are distant five minutes from the Parliament like Sant Micheal Cathedral and the synagogue.