The Ranch in Fort Myers is part saloon, part concert hall. Think the “Rawhide” scene from The Blues Brothers but with a mechanical bull and an occasional appearance by a legendary band like The Wailers. Outside of the arenas and concert halls, there’s not a better spot in Southwest Florida for music.
For an Out-of-Place Dive Bar
Paddy Murphy’s Irish Pub on Fifth Avenue South has managed to outlast all its cohorts from a time when Naples’ famous main drag wasn’t so posh. But who knows how long it will be around, as the rest of its block has already been redeveloped. Make sure to stop by this legendary haunt.
Off the Hook Comedy Club has been bringing in top-flight comedians to Naples for more than a decade now, from a pre-fame Amy Schumer to war horses like Kevin Nealon and Jim Brewer.
For Singing Journey Tunes at 11 p.m. on a Wednesday
BackStreets Sports Bar in Cape Coral is the only place that offers karaoke seven nights a week, from 9 p.m. to 2 a.m. So, Don’t Stop Believing you can hit those high notes.
For a Refined Experience
Although it is going through extensive renovations, Artis—Naples is still the best place to spend an evening enjoying the best cultural experiences Southwest Florida has to offer. From classical music to Broadway musicals, the world’s best performers come here.
For Confusing Your Out-of-Town Friends
Tell them to meet you at the North Naples Country Club. No need for tennis whites or a jacket for service. Heck, shoes and a shirt are barely required. But this is one of Naples’ best neighborhood bars.
For Turning Your Pub Crawl into a Bar Spin
Pedal Pub SW Florida takes you and 14 of your closest, most active friends on a BYOB pedal barhopping experience through downtown Cape Coral or North Naples, with Fort Myers coming soon. Think of it as the only carpool fueled by booze.
For Wild Nightlife
Take the whole family to Corkscrew After Hours at Corkscrew Swamp Sanctuary. Every month, this Audubon sanctuary opens for one night to let us explore wild Florida under the stars, which are magnificently visible there.
For a Beach View
On a night with a particularly good moon, head to the Fort Myers Beach Pier or Naples Pier, both of which are open 24 hours a day.
For a Late-night Bite Worth Eating
Fifth Avenue South’s Bar Tulia is just about the only place in Southwest Florida where you can get any Instagram-worthy food after midnight. Get the pigs ears. Trust me. And maybe one of their spectacular house cocktails as a nightcap.
For Rooting on the Home Team
Everyone likes cheering for a winner. And no one has consistently won more than the Florida Gulf Coast University women’s basketball team. They are off to another fantastic start and look once again to be in contention for an NCAA tournament run.
For Showing Off Your Smarts
For Showing Off Your Smarts The Pub at Mercato offers up one of the most challenging trivia nights around. You legitimately need to know a little about a lot—world history, sports, pop culture, geography—to have a chance to win. Plus, they offer themed nights, such as Harry Potter or Disney trivia, so that you can proudly show off your inner nerd.
Related: How to Take a Nightlife Adventure