St. Michaels

Many might know the sleepy town of St. Michaels, Maryland, for its cameo in the 2005 film Wedding Crashers, but East Coasters know it as a peaceful waterfront escape that’s an easy weekend away for luxury seekers from cities like Baltimore, Washington, D.C., Philadelphia and New York.

Most popular during the warm summer months, this tiny town on Maryland’s Eastern Shore has a rich history dating back to 1677. Today, the town seamlessly blends history (check out the Hooper Strait Lighthouse and the Chesapeake Bay Maritime Museum) and culture with luxe hotels and posh shops and restaurants.

It’s a playground for the elite — political boldfaced names like Dick Cheney, Donald Rumsfeld and media maven Greta Van Susteren currently own or have owned homes on Maryland’s Eastern Shore — but it’s also a quiet town filled with just more than 1,000 full-time residents. A stroll down Talbot Street, the town’s main strip, feels very much like it did 15, 25 or even 50 years ago, evoking a sort of Mayberry-eqsue nostalgia and decidedly down-home charm that is hard to find elsewhere.