Once the sun starts to drop over the Gulf, Fort Myers Beach shifts into a different gear. Times Square, the walkable strip near the north end of the island, is where most evenings on the island end up, and for good reason: it is the one place on Fort Myers Beach where you can park the car, kick off your sandals, and wander between dinner, a scoop of ice cream, and live music without any real plan.
The district is still rebuilding piece by piece after Hurricane Ian, and that is part of what makes visiting right now interesting. New restaurants and shops are opening alongside old favorites that reopened first, so a walk down the strip feels a little different every season. Street performers and small bands often set up near the fishing pier in the evenings, and the crowd is a mix of longtime locals, snowbirds, and families staying just up the beach.
Start early if you want the beach itself without the evening crowd. The stretch of sand right behind Times Square is wide and easy to reach, and it is a good spot to watch the pier fill up with anglers as the light turns gold. From there, it is a short walk to pick a spot for dinner, whether that is a casual counter for fish tacos or a table with a Gulf view for something slower.
Shopping along the strip leans toward beach practicals and local goods rather than big-box anything: swimwear, souvenirs, art from Gulf Coast makers, and the odd shop that has been there long enough to remember the island before the storm. It is worth popping into a few even if you are not buying, just to hear how people talk about the place they call home.
One tip for anyone staying with us: Times Square gets busy on weekends and during the winter season, so if you are set on a specific restaurant, it is worth calling ahead. Parking near the strip fills up fast too, and many of our guests find it easier to walk or bike in from their home rather than drive.
This is exactly the kind of local detail we like guests to have before they arrive, not after. If you are planning a trip and want a home within easy reach of Times Square and the rest of Fort Myers Beach, check availability with Anchor & Isle and we will help you find the right fit.
