October 2023
Is there anything better than the beach in October? Home to one of the most picturesque boardwalks, John’s Pass Village and Boardwalk offers shopping, casual dinning and a cigar shop that has on site hand rolled offerings (Cuban paradise cigar and cafe). The Treasure Island Beach Trail is a must do paved biking and walking trail that runs parallel to the Gulf of Mexico. Awesome high end restaurants are plentiful within a reasonable drive or ride share, with IL Ritorno headlining the upscale Italian scene.
Must Do:
Perched in the heart of John’s Pass Village, the brewpub occupies a lively upstairs space with an industrial‑warehouse vibe, exposed tanks, colorful art, and a long inviting bar. They brew on site and keep about 20 rotating taps flowing, ranging from sessionable day‑beach beers to bold pours. Expect a lively mid‑afternoon happy hour, great for chilling post‑beach.
Visiting Crabby’s On The Pass is like stepping into a laid‑back seaside escape—part restaurant, part marina party, all waterfront charm. Perched along the John’s Pass waterway, they are known as the “World’s Longest Waterfront Bar” with dining decks right over the docks. Inside, you’ll find a spacious, nautically decorated interior with high ceilings, exposed beams, and large windows framing gorgeous boat‑and‑dolphin views. Check their website for live music schedules.
