Windstar Cruises Caribbean: 8 nights from Bridgetown with Star Legend
Dec 4, 2026

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

Saint George

Bermuda's Historic Charms from Saint George!

Set sail on a delightful cruise from Saint George, Bermuda, a charming and historic town that is a UNESCO World Heritage site. With its pastel-colored buildings, narrow alleyways, and rich colonial past, Saint George offers a picturesque and tranquil departure point for your island escape. Experience the unique blend of British heritage and island serenity before embarking on a journey filled with sun, relaxation, and unforgettable Bermudan discoveries.

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.