Times Square is the little pedestrian plaza at the foot of the Matanzas Pass Bridge where Old San Carlos Blvd meets the beach, and it is where most of the island’s evening energy collects. Think ice cream shops, beach-gear stores, a clock tower to meet under, street musicians and a handful of casual bars and restaurants all within a two-minute stroll of the sand.
It sits right beside the public beach and the pier, so it works as the end point for a beach day: rinse off, wander over, find a table. Most places are relaxed about sandy feet and swimsuit cover-ups. Live music tends to start in the late afternoon and carries on into the night, and there is nearly always something happening at the weekend.
Parking can be tight in season, so we’d suggest arriving before the sunset rush or using the trolley that runs the length of Estero Blvd. Come for sunset, stay for dinner and a stroll, and you’ll see why it is the island’s front porch.
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