Known for its markets and its striking 19th-century limestone architecture, Kingston is a great base for exploring the Thousand Islands and the St. Lawrence River and its national park. Visit Wolfe Island on the free ferry, or hunt for antiques in nearby villages.

Funchal, the capital of the Madeira archipelago, was declared a city in the 1500s, and became an important point between the old and new worlds. The laid-back city owes much of its historical prominence to the white gold, the Madeiran sugar. Today Funchal is known for its appealing temperatures, wine and crafts. Top spots to visit include the open Worker's Market, Blandy's Wine Lodge and the Sacred Art Museum. Friendly locals, walkable streets and cheap taxis make the city easy to get around.