Fort Myers Beach offers a few distinct areas for evening entertainment.The main nightlife area is generally around Times Square, at the northern end of Estero Island. Here, you'll find a collection of casual bars, beachside pubs, and restaurants that often feature live music well into the evening. It's a lively spot, particularly around sunset and on weekends, with many places offering outdoor seating overlooking the water.Further south along Estero Boulevard, you'll encounter a mix of standalone bars and establishments connected to resorts. These spots often have a more relaxed feel, with some offering live entertainment such as acoustic sets or cover bands. It's less concentrated than Times Square, so you might need to drive or use a ride-share service between venues.As another option, consider heading off the island to mainland Fort Myers. The River District in downtown Fort Myers has a growing selection of bars, pubs, and restaurants, some with live music.