Ruggles, Newport, RI
A legitimate big-wave surf spot on the East Coast? In tiny Newport, Rhode Island? The answer to both of these questions is yes. Right behind some of the East Coast's most historic and lavish mansions (including a little one owned by some people named Vanderbilt) lies Ruggles, a surf mecca with an exposed reef and wave that breaks far out on a point over hardcore rocks. This water requires serious boarding experience, but its right-to-left breaking wave is almost always going off, and the farthest point out is famous for genuinely large waves that curve themselves into sizable barrels you can slide right through.
Newport hasn't lost its yachting-and-popped collar airs, but some of the shops at Bowen's Wharf have entered a more modern era, and Island Surf & Sports handles the town's surf gear needs. We also recommend running the famous 3.5 mile, 150-year-old Cliff Walk over the surf (try to find the 40 steps that plunge down to the beach), or cruise Ocean Drive along the coast up to Fort Adams for dramatic sea views.
Should you encounter a flat day, try water sports (get rental equipment at the wharf including Jet Skis, small boats, kayaks, and sailboats from Sight Sailing). Or go preppy and check out the International Tennis Hall of Fame as well as the Newport National Golf Club, recommended for its evergreen fairways and cracked-seashell paths. Of course, it's hard to find a reliable hotel in Newport that doesn't indulge in extravagance, but the main reason to stay at the renovated Victorian-style Castle Hill Inn is its 40 acres on the ocean and artisan-wood-and-white-linen rooms, especially if you're staying in one of the beach cottages set in the dunes.
As for restaurants, the wharf-set, nautical-style 22 Bowen's Wine Bar & Grill garners compliments from diners tired of eateries stuck in the 1980s; it's a hit when it comes to post-surf dining with modern-prepared seafood, steaks, a raw bar, and a large list of varietals. Just don't leave town without a bowl of uncommonly savory New England-style clam chowder at the Black Pearl. Claus von Bulow wouldn't have it any other way.