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.

Inviting beaches and tiny shops selling local treasures welcome you to this quiet island haven. Don't miss dining with your feet in the sand at Foxy's on the beach-a perfect lunch stop!

San Juan, Puerto Rico's capital and largest city, sits on the island's Atlantic coast. Its widest beach fronts the Isla Verde resort strip, known for its bars, nightclubs and casinos. Cobblestoned Old San Juan features colorful Spanish colonial buildings and 16th-century landmarks including El Morro and La Fortaleza, massive fortresses with sweeping ocean views, as well as the Paseo de la Princesa bayside promenade.