Boston — Red Sox, Oysters & Harpoon, MA

Day one: Freedom Trail walking tour from Boston Common to the Old North Church, then Neptune Oyster for the lobster roll that rewrote the rulebook. Harpoon Brewery taproom in the Seaport for a flight and a kitchen full of smoked meats. Night two: Red Sox at Fenway Park, bleachers or box seats depending on the crew's tolerance for standing room. Post-game drinks at Eventide Oyster Co. on Congress Street—raw bar, brown butter lobster roll, and a wine list that doesn't apologize. Final night: Row 34 on the waterfront for sea urchin, scallops, and a beer list that rivals the oyster selection. Rooftop drinks at Thinking Cup or a late-night dive at The Friendly Toast.