The legendary Hamptons, a cluster of wealthy enclaves on Long Island's South Fork, remains a celebrity summer playground, with splashy restaurants and nightclubs galore. But lovely beaches, fishing and kayaking attract off-the-A-list visitors, as well. Old money oozes throughout Southampton, while new wealth reigns in East Hampton. Montauk is a hit with fishermen and surfers. The Long Island Railroad travels the Hamptons in an hour. The Sag Harbor Whaling Museum and Montauk lighthouse are popular stops.

What happens when a "gassy" Englishman rows into town feeling thirsty? A pub is born. And from that a city—in this case Vancouver. Though the pubs are plentiful, food and drink aren’t the only things to take in during your trip. In its 150 years, Vancouver has grown into a cosmopolitan city nestled in the great outdoors. Enjoy the snow-capped mountains, waterfront forests, cityside beaches, Olympic history and the world’s highest suspension bridge. Hipsters welcome. (Don’t worry, they don’t bite.)

The town that gave the country (and port wine) its very name, Porto is Portugal’s second-largest metropolis after Lisbon. Sometimes called Oporto, it's an age-old city that has one foot firmly in the industrial present. The old town, centered at Ribeira, was built on the hills overlooking the Douro River, and today is a UNESCO World Heritage Site. The 14th-century São Francisco church is a main attraction, as are the local port wine cellars, mostly located across the river at Vila Nova de Gaia.

Coastal Calpe seems straight from a postcard, with a dramatic rocky headland and palm-dotted beaches lapped by Mediterranean waters. Once an ancient fishing village, the Costa Blanca town mixes Roman ruins and scenic nature parks with plenty of modern urban comforts.

History lovers should know that Milan is not all about trendy shops and designer clothes. Among the city's many historical attractions are La Scala Opera, the Milan Cathedral, the National Museum of Science and Technology and Santa Maria della Grazie, the church that preserves da Vinci's "Last Supper".