Nothing epitomizes blue-blooded New England aristocracy like Newport. The famous resort town has been the summer home of the nation's elite, from business magnates to Commander-in-Chiefs: Presidents Dwight D. Eisenhower and John F. Kennedy both had "Summer White Houses" here. The only reminder you need of Newport's historic chichi status is a drive down mansion-studded Bellevue Avenue: colossal homes (cheekily known as "cottages") line the cliffs, built by families such as the Astors and Vanderbilts during the Gilded Era.
Summer is when Newport truly comes alive. It is host to the Newport Jazz Festival and Folk Festival, and as the "yachting capital of the world," is the site of regattas and a vibrant yachting and sailing community. (Newport's nautical obsessions may have something to do with its significant role in the creation of the US Navy). Well-preserved historic buildings and seafood restaurants brush up against the International Tennis Hall of Fame, and there's a vibrant Portuguese and Caribbean immigrant community.
Of course, if you come in the winter, be prepared for an off-season vibe throughout the city.
Staying on Thames Street (the main waterfront drag) puts you in the heart of Newport's action. If mansion-gazing has you yearning for a regal Newport experience (especially in price), head west to Castle Hill: the views of the Narragansett here are breathtaking.