Lisbon to Bridgetown

One of Europe’s smallest capital cities, Lisbon is for many, one of it most beguiling – an easily accessible mix of new and old worlds. Elegant outdoor cafés line Lisbon’s mosaic cobblestone sidewalks along grand 18th-century boulevards. Turn-of-the-century funiculars dot its steep hills. Two-thirds of the city was leveled in a 1755 earthquake, but in its churches, peeling buildings, tiny alleyways, hidden squares, you can still feel the glorious past.

An infectiously happy island, with beautiful beaches, balmy weather, and a delightful British flair. As a result of its successful sugar economy in the 17th- to 19th-centuries, you’ll find large manor estates full of fine Barbados mahogany and antiques, along with gaily painted wooden frame houses– the essence of the festive Caribbean. Rum rules in Barbados, and, over the centuries, cane plantations have divided the Bajan landscape into a pretty patchwork of fields, coconut and royal palms, breadfruit, oleander, and citrus trees.

Life in Bequia revolves around the sea. Walk through the pretty town of Port Elizabeth, set on one of the loveliest and best-sheltered harbors in the Caribbean, and you’ll see fish nets drying in the sun. Boats are built on the beach in the shade of palm trees, and many yachtsmen have come here to have a fine schooner built by hand. (Or take home a model ship, perfect in detail.) Once an active whaling station, Bequia today is a favorite among Caribbean insiders and yachties for its unspoiled beauty and easy pace.

St. George’s is the capital city of the Caribbean island of Grenada. In the town center, the 18th-century Fort George offers panoramic views of the island and St. George’s Bay. Nearby, Fort Matthew was formerly a battleground and, later, an asylum, and has underground tunnels. The Grenada National Museum hosts exhibits about the history of the region, including the plantation economy and the whaling industry.

Kralendijk is the capital of Bonaire, a Dutch island in the Caribbean Sea. Colorful architecture dots the shopping street of Kaya Grandi. The Bonaire Museum displays archaeological finds, shells and old photos. Off the coast is Bonaire National Marine Park, with a coral reef sheltering tropical fish. This stretches west to Klein Bonaire Island, where the sandy beaches provide a nesting ground for sea turtles

The people of the Netherlands established a trading settlement at a fine natural harbour on the Caribbean island of Curaçao in 1634. The town developed continuously over the following centuries. The modern town consists of several distinct historic districts whose architecture reflects not only European urban-planning concepts but also styles from the Netherlands and from the Spanish and Portuguese colonial towns with which Willemstad engaged in trade.

When it comes to the Caribbean, many islands are blessed with sugar-white beaches, tall palm trees, and friendly bartenders serving up umbrella-topped drinks. But Aruba is like no other island. Over the years, its Dutch West Indies mix of ethnicities has nurtured a deep and interesting cultural mélange—as well as fine cuisine, refined shopping, and vibrant stage shows. Add to that an outdoor world of internationally significant locations for fun-seeking folks of all ages. There is simply no better place on the planet to learn and enjoy windsurfing. The world-renowned steady breezes that fill the sails also keep us cool in a deep Caribbean location that is blissfully below the hurricane path. Sun always shines on our pristine beaches, and that brings a truly global group of travelers to our shores.

Cartagena is a port city on Colombia’s Caribbean coast. By the sea is the walled Old Town, founded in the 16th century, with squares, cobblestone streets and colorful colonial buildings. With a tropical climate, the city is also a popular beach destination. Reachable by boat are Isla de Barú, with white-sand beaches and palm trees, and the Islas del Rosario, known for their coral reefs.

The San Blas islands stretch along approximately 200 miles of Panama’s Caribbean coastline and San Blas reservation, also known as the Kuna Yala, is defined from the seaward continental shelf to the top of the jungle-clad continental divide some miles inland.

Colón is the capital of Colón Province, in Panama. It sits on the Caribbean coast, at the entrance to the Panama Canal. The Canal Expansion Observation Center is a park with viewing platforms over the canal’s Atlantic locks and Gatún Lake. The vast Colón Free Trade Zone offers tax-free shopping. Just west of the city, at the mouth of the Chagres River, Fort San Lorenzo is a well-preserved colonial military structure.