The Isles of Capri sit at the end of a two-lane road south of Naples, and most people drive right past them. That’s exactly what makes Island Gypsy Cafe & Marina Bar so good. Anchored on the Capri Marina on Tarpon Bay, this waterfront spot is the definition of Old Florida: weathered dock vibes, fresh Gulf seafood, an oversized bar, and a stern of the actual Island Gypsy boat built into the décor. Chef Sam Phillips keeps the menu tight and local: coconut shrimp, mahi mahi, mussels, and fresh-catch specials. The legendary carrot cake alone is worth the drive. Come by land or pull up by boat, either way, you’ll stay longer than you planned.
Thirsty for more? Dive into the Bum’s full guide to the best beach bars in Florida.
