Ocean Crossings – 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.

Funchal is the capital city of Portugal’s Madeira archipelago. It’s backed by hills, and known for its harbor, gardens and Madeira wine cellars. The centuries-old Funchal Cathedral, which mixes Gothic and Romanesque styles, is notable for its carved wooden ceiling. Fronting the harbor is the São Tiago Fortress, built in the 1600s. It now houses the Contemporary Art Museum, with a large collection of Portuguese works.

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.