Leave the crabbing to the experts at downtown’s Truluck's seafood, steak, and crab house. The Florida stone-crab season extends through May 15, and this is the place to get ’em: Truluck's operates a fleet of twenty crabbing boats at its private fishery on the nearby Isle of Capri. Reserve well ahead, or just go for the early-bird dinner at the bar.
Fifteen minutes north of downtown, Naples Tomato incorporates ten varieties of its namesake fruit, including imports from San Marzano and now-in-season local heirlooms, into its seafood-heavy Neapolitan menu. Stop in the wine bar first and then tuck into one of 30 homemade pastas, like the truffle ravioli or always-popular lasagne.
Watch—and be watched by—pelicans at the open-air Dock at Crayton Cove, on Naples Bay. The Dock’s Caribbean- and Latin-spiced seafood is best enjoyed at lunch, when you can grab a grouper sandwich caught that morning (order it blackened). Even better: Catch it yourself, and they’ll cook it—any way you want, with two sides, for $12.95.