Windstar Cruises Caribbean: 8 nights from Bridgetown with Star Legend
Dec 4, 2026
Barbados, Saint Lucia, Trinidad and Tobago, Saint Vincent and the Grenadines, Netherlands Antilles, Aruba
Cruise itinerary
Departure Port: Bridgetown ➞
Landing: Oranjestad
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Friday, December 4, 2026 - 6:00 PMBridgetown
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Saturday, December 5, 2026 3:00 PM - 8:00 AMRodney Bay
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Saturday, December 5, 2026 5:30 PM - 6:30 PMPitons
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Sunday, December 6, 2026 8:00 AM - 5:00 PMScarborough
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Monday, December 7, 2026 8:00 AM - 10:00 PMBequia
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Tuesday, December 8, 2026 8:00 AM - 6:00 PMMayreau
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Wednesday, December 9, 2026Navigation
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Thursday, December 10, 2026 8:00 AM - 10:00 PMKralendijk
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Friday, December 11, 2026 8:00 AM - 6:00 PMWillemstad
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Saturday, December 12, 2026 6:00 AM 11:59 PMOranjestad

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.
Bridgetown is one of the oldest cities in the Caribbean; its architecture with balconies of colonial buildings blending with warehouses and brash modern office blocks fascinates and entertains visitors. The center of activity is the careenage, a marina that borders the Barbados Parliament (home to two small but fascinating local history museums). A number of the island's most important religious buildings are located within a five-minute walk of Parliament, including St. Michael's Cathedral and a synagogue.

Rodney Bay

Pitons

Scarborough
Scarborough is the largest city in Tobago, one of the two islands of the Republic of Trinidad and Tobago. It has about 17,000 inhabitants, almost a third of the island's population. The city is dominated by Fort King George, an eighteenth-century fortification named after the British King George III, which today houses a History and Archaeology museum. Scarborough is the capital and deep-water port of Trinidad and Tobago, and its administrative center. Located on Rockly Bay, the city is situated on the slopes of a hill 13 km from the south-western tip of Tobago. At the top of the hill there is Fort King George built by the British in the late 1700s. Scarborough has several facilities dating back to the 19th century, including the House of Assembly, a finely restored Georgian building. The city has benefited considerably from the growth of tourism in Tobago and has many commercial buildings. Tobago Airport, Crown Point, is about 11 km from Scarborough and handles domestic and international flights. Outside the port you will find vendors of traditional homemade sweets - sugar cakes (grated coconut cooked in milk and sugar) and sweets made of sticky sesame seeds held together by sugar and caramelized.
Bequia
Escape to Paradise from Bequia!Set sail on an idyllic Caribbean escape from the enchanting island of Bequia. This serene and unspoiled gem in the Grenadines offers a tranquil and intimate starting point for your cruise. Experience the laid-back charm and pristine waters before embarking on a journey to discover secluded coves, vibrant coral reefs, and the untouched beauty of the Lesser Antilles, promising pure relaxation and natural splendor.

Mayreau

Kralendijk
Kralendijk is the capital of the island of Bonaire in the Dutch Antilles, located in the Caribbean Sea off the coast of Venezuela. Surrounded by a coral reef that makes its fame worldwide, the city has a rich cultural heritage that attracts many tourists every year, thanks to its rich flora and fauna. The island of Bonaire was discovered by Alonso de Ojeda and Amerigo Vespucci in 1499, it was then part of Spanish territory. Then, in 1633, it was the turn of the Dutch to own the island. Subsequently, the Dutch Antilles became French, in 1805, after the conquest of Napoleon. In 1816, following the Treaty of Paris, it was returned to the hands of the Dutch. The abolition of slavery date occurred in 1863. Almost a century later, in 1943, Flamingo International Airport was built, promoting the development of the island. Bonaire obtained its independence on October 10, 2010. The boomerang-shaped port is full of cruise ships that stop to allow a visit to tourists. The city of Kralendijk offers paved roads with some shops, restaurants, and bars on the waterfront. Nearby is Fort Orange, built in 1639 to defend Bonaire's main port. The center of Kralendijk is the ideal place for shopping, shops are generally open from 8 am to noon and from 2 pm to 6 pm. This place is much quieter and more relaxed than the other ports in the Dutch Antilles. The splendid Bonaire National Park is considered one of the best diving destinations in the Caribbean, while Washington-Slagbaai Park in Brandaris is the highest point on the island. Other popular sites to see are the salt pyramids and the Willemstoren lighthouse.

Willemstad
Capital of the Dutch Antilles and largest city on the island of Curacao, this town, a large and small city at the same time, is full of life and attractions for all tastes.
The vibrant capital of Curacao is a welcoming, cheerful destination, with two distinct historic districts, divided by the beautiful bay of St. Anna. Punda, site of narrow, clean streets, is packed with shops and museums. Otrobanda, or "The Other Side", is a labyrinth of residential streets, in contrast to the organized grid throughout the bay. The colorful colonial architecture of Willemstad has been named a UNESCO heritage site. Diving and swimming with dolphins are popular and highly sought-after activities throughout the bay.

Oranjestad
Oranjestad, the historic Dutch capital of Aruba, is located along the picturesque south coast, and it is considered a paradise for the senses by every tourist.
Boutiques, exclusive shops, street vendors, casinos and a wide range of restaurants, discos and bars make Orajestad a very popular tourist destination in Aruba. In addition to shops, restaurants and entertainment, in the city you can visit museums, a butterfly farm, art galleries, golf, historical sites and a functional touristic port. The colonization of the island by Netherlands is demonstrated in Dutch colonial architecture that is mixed with distinctly Caribbean brightly coloured buildings.
Boutiques, exclusive shops, street vendors, casinos and a wide range of restaurants, discos and bars, make Oranjestad, a super popular tourist destination in Aruba. In addition to shops, restaurants and entertainment, this capital city of the island offers museums, a butterfly farm, art galleries, golf, historical sites and a functional marina. The colonization of the island by the Netherlands is demonstrated in Dutch colonial architecture, mixed with buildings with distinctly Caribbean bright colors.