Waterfront vacation homes offer a relaxed retreat for letting your hair down, taking your shirt off, and eating casual meals, with your shirt still off. Asking that you wear a shirt, but still keeping things casual: Hell Point Seafood
From the chef/owner of Foggy Bottom's upscale Kinkead's, Hell Point brings Beard Award-winning cred to the Annapolian waterfront, but with a more leisurely vibe and price point; the name pays homage to neighborhood's violently sketchy past, before it was gentrified by the Naval Academy, who'd deemed it too "hardscrabble" for its cadets (so how did they feel about Iwo Jima?). Seating 270, the space is broken down into three breezily elegant stories: an airy, top-floor dining room with white columns and lattice-work booths; a wide-open, blue- and purple- walled, mid-level terrace with cast iron chairs resembling huge clams; and a tile-floor ground-level dominated by a granite bar, where you will part with your own clams. Mid-Atlantic seafood includes fried squid w/ green papaya salad & lime-chili dipping sauce, blue hill bay mussels w/ Thai yellow curry & coconut milk, crispy blackback flounder w/ tasso ham & crayfish tails, and porcini-broth'd roasted rockfish, a traditional dish that quietly disapproves of rocklobster's cocaine-fueled orgying
As for boozing, there're 120 bottles of wine, shloads of bottled beers (including locals like Flying Dog, Silver Spring's Hook and Ladder, and Annapolis' own Fordham), and specialty cocktails like the sugarcane-stick'd "Hell Point Coconut Mojito", the vodka, orange juice, & chardonnay "Annapolis Sun", and the gin/lemon juice/bubbly "Champagne Fritz" -- the nickname you'll ask people to call you as you retrieve a cherry tomato out of your belly button.