Bridgetown is the capital of Barbados, a compact Caribbean city whose historic centre — the Careenage waterfront and the streets around it — was inscribed as a UNESCO World Heritage Site in 2011. It is small enough to walk across in an hour, but dense enough with history that you can spend a satisfying few days here without running out of things to see.
The historic centre clusters around National Heroes Square, where the Parliament Buildings — one of the oldest continuous legislatures in the Western Hemisphere — face the waterfront. Broad Street runs west from the square, loud with commerce; the quieter streets behind it hold the Nidhe Israel Synagogue and museum, one of the oldest Jewish congregations in the Americas, and St. Michael's Cathedral, where George Washington attended services during his only trip outside North America.
South of the centre, the Garrison is a British colonial military complex that now holds the Barbados Museum — the best on the island — and a racecourse that doubles as a social institution. Queen's Park, east of the centre, is worth visiting for the thousand-year-old baobab tree alone.
Carlisle Bay, just south of the city, offers the nearest good swimming: calm turquoise water, sandy bottom, sea turtles, and five shipwrecks for snorkellers and divers. Cricket fills the rest of the calendar — Kensington Oval is one of the legendary grounds in the West Indies, and a Test match here is an occasion worth planning a trip around. For rum, the Mount Gay Visitor Centre does justice to the world's oldest commercial rum brand.