Watch Hill

For generations, this seaside village has attracted movers and shakers looking for a low-key getaway. Watch Hill has nearly 2 miles of gorgeous beaches, including Napatree Point Conservation Area, a great spot to see shorebirds and raptors and take in the sunset. Stargazers might catch a glimpse of Taylor Swift or Conan O'Brien, both of whom have homes here. The heart of the town is Bay Street, a seasonal business district with boutiques selling upscale beachwear, fashions, home goods, T-shirts, and souvenirs. There are also cafés and a historic carousel.