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Sanibel is pretty family-oriented, so there’s not a huge selection of nightlife. There are a few options, however, such as the Beaches Bar & Grill, at the Sundial Beach Resort, which has live music and dancing starting at around 9 pm. And it’s usually pretty lively The Fish House, with sports on the big-screen TV. There are a few other sports bars, as well, including the two Lazy Flamingos, Doc Ford's and the Sanibel Grill. Or, catch a movie at the Island Cinema on Tarpon Bay Road.
Live music can usually be found at various places around the islands. Jacaranda Lounge has live music. There's the very popular NASCRAB races at Tween Waters Inn on Captiva on Mondays and Thrursdays at 6Pm [family] and 9PM [adults]. Tween Waters also has live music on an irregular schedule. Other places offer entertain but schedules vary with season. BIG Arts has live performances, usually 1 nite, by well know artists. There is Schoolhouse Theater with plays and musical reviews. George and Wendy's Seafood Grille has Live music on Friday and Saturday nights and Karoake on Thursdays. Call to confirm as sesonal schedules change.
Also up on Captiva you'll find live music at the Mucky Duck, where visitors gather and get a drink for the bar [beer and wine] and watch the sun go down while enjoying live music. Doc Ford's in Chadwick Square is now open! They also have Live entertainment and and outdoor patio Outdoors. R.C. Otters and Key Lime Bistro also offer music lunch and dinner. Outdoors.
Stop at the Visitor Center and pick up the weekly schedule of live entertainment.
If you are looking for more "action", you can head off island to Fort Myers Beach. It's only about 10-15 minutes away from the bridge and has a more lively nightlife- especially for the younger crowd. After you're done, you can slip back across the bay and get a quiet night's sleep on Sanibel!
If you are looking for an opportunity to do ballroom dancing with live music, there's live music every night (at least in season) at the Island Inn. The entertainment is in the dining room, so you can listen to it during dinner. There's also a bar where you can have a drink and listen to the music or dance.