WATCH HILL, R.I.: Newport's quieter sister, Watch Hill abounds with rambling manses and old-school charm. Pick up sandwiches on the way in at The Cooked Goose in Westerly (try the "C.M.R." or the "Aphrodite") before hanging your hat at the Ocean House, a beautiful seaside resort that was recently restored to its former grandeur. (Bring dress whites for the regulation croquet court!) Après beach, take a spin on the Flying Horse Carousel and check out the gorgeous yachts docked at the Watch Hill Yacht Club. After washing the sand off, grab dinner and drinks alfresco at the Olympia Tea Room. When you're ready to go, head out by way of rail, air, or sea.
Clockwise from top left: Canvas coal bag by ACL & Co., $68, here; J.Crew plaid shirt, $68, in stores; Cartier Tank Solo watch, $2,300, in stores; Asprey propeller keyring, $270, here; Sperry Top-Sider boat shoe, $75, here; Hermès "Yachting" beach towel in horizon blue, $180, here; Wölffer Estate 2010 Rose, $16, here.