A headquarters of sorts for genteel vacationing on Chesapeake Bay, the Inn at Perry Cabin sits at the end of a long, straight, tree-lined drive. This clapboard compound has lots of fun stuff on-site: think kayaks, a croquet court, afternoon tea, and Miss Gussie’s sweets at turndown. Classic hangings (prints of sea shells, English hunting parties) set the tone, and walls in the understated rooms are painted periwinkle blue. If you dig nautical vibes, you'll love it here.
The main drag of quaint, historic St. Michael’s is within easy walking distance. My girlfriend and I went the other way, though, jogging a few miles to a homey seafood joint called Chesapeake Landing. They didn’t seem to mind that we showed up dripping sweat, and brought me half a dozen local crabs for a mere $12.50—very satisfying, even if it took about as much work to crack through the shells and get to meat as it had to run there!
Back at Perry Cabin, we lay out by the pool and watched the sun set from the lawn on Fogg Cove. We ate oysters and a remarkably flavorful dish of diver scallops at the on-site restaurant. I had the open-faced BLT breakfast sandwich the next morning, and I'm not exaggerating when I say the butter-drenched brioche melted in my mouth.