To find out what's going on during your stay, pick up a copy of the daily News-Press (www.news-press.com). The two local tabloids, Beach Bulletin and Fort Myers Beach Observer, are available at the chamber of commerce.
The area around Times Square is always active, every day in winter and on weekends in the off season. At the foot of Lynn Hall Memorial Pier, the Beach Pierside Grill, 1000 Estero Blvd. (tel. 239/765-7800; www.piersidegrill.com), has live entertainment on its beachside patio. It's not directly on the beach, but locals in the know head for the rooftop bar at Beached Whale, 1249 Estero Blvd. (tel. 239/463-5505; www.thebeachedwhale.com), which supplies free chicken wings during its nightly happy hour. Rock and reggae music are played downstairs for dancing.
Away from the crowds in the "middle beach" area, the Junkanoo Beach Bar, under Anthony's on the Gulf, 3040 Estero Blvd. (tel. 239/463-2600; www.junkanoo-anthonys.com), attracts a more affluent crowd for its bohemian-style parties that run from 11:30am to 1:30am daily. Live bands here specialize in reggae and other island music. On the menu are inexpensive subs, sandwiches, burgers, and pizzas, and a concessionaire rents beach cabanas and watersports toys, making it a good place for a lively day at the beach.
On Sunday afternoons, revelers jam the docks for the famous outdoor reggae parties at the Bridge Waterfront Restaurant, 708 Fisherman's Wharf (tel. 239/765-0050; www.thebridgerestaurant.com), which is under the Sky Bridge on San Carlos Island.