Newport, Rhode Island. Home to salty sailors, ghosts of American dynasties past, and one helluva preppy party scene. Pack your Sperry Top-Siders, because this boat is about to get rocking.

Peachy bed-and-breakfasts dot downtown Newport. However, we prefer to stay posh at The Chanler. Request a villa (because no vacation should be without a private hot tub). Quick tip: Parking around town is impossible. Allow for extra time or rent a bike.

Forget the Astors. The richest residents of Newport are the croque monsieurs from Rosemary and Thyme Boulangerie & Cafe.

If you don’t order fresh baguette sandwiches for later, hit up Flo’s Clam Shack just off Easton’s beach.

Even on clear days, the waterfront patio at The Black Pearl is dark and stormy (in the best way).

After the sun sinks, head to Perro Salado for spicy cucumber margaritas by the pitcher, guac, and chili-dusted scallops.

For market-fresh fare, book a table at Tallulah on Thames (the restaurant also runs a taco cart; follow @tallulahstacos on Twitter for locations).

Let your yuppie flag fly on the lawns of the International Tennis Hall of Fame and during a private lesson from Sail Newport.

Divot stomping at the weekly Newport International Polo Series is ideal if you’d rather just horse around.

Hobnobbing with Ivy Leaguers is tough. A deep-tissue rubdown at Hotel Viking’s SpaTerre works out the gimlet-induced kinks. 

Tour Rosecliff (a.k.a. the mansion where 1974’s The Great Gatsby was filmed) for a closer look at Gilded Age opulence.

Get plenty to tweet about during a photography workshop at the Norman Bird Sanctuary.

Shop along Thames and Spring Streets for kitschy trinkets, doodads made with shells, and hand-blown glass figurines (pop into Cold Fusion for gelato while you’re ambling).

After your Thames Street excursion, unwind and uncork with shared plates, cheese, and plenty of vino at Fluke wine bar. Not as glitzy as the Manhattan club of the same name, The Boom Boom Room is still a fun place to shake your pearls.

Finish nights at the cafe-by-day, club-by-night joint, The Fifth Element.

We can’t wait to get on the Rhode again.