South Carolina’s second-oldest city is set on a coastal isle surrounded by a backdrop of marshes, old rice plantations, and moss-draped live oak trees. Sporty types can rent a kayak and explore a dolphin-filled maze of tidal creeks; other activities include shopping along Bay Street and gawking at the antebellum manses in the Old Point neighborhood. For dinner, go for fresh, locally caught fish (and grilled pork belly) at Breakwater Restaurant & Bar, and stay the night at Anchorage 1770, a gracious, pet-friendly inn with an upper-level porch offering gorgeous water views.