How to Take a Nightlife Adventure in Southwest Florida

An insider's guide to the best places for stepping out.

by

Y ou could easily make a string of insult jokes about the definition of nightlife in Southwest Florida. “It’s what you call the 15 minutes between sunset and it actually getting dark out.” “It’s the two hours after the Mel’s Diner early-bird special ends.” But this is the Love Issue, and true love looks past flaws to find beauty. Plus, there really is a lot to love about nightlife in our region.

Certainly, if you are looking for masses of sweaty, drunk clubgoers bouncing to the latest beats (or whatever it is the kids do these days), this isn’t the place. But that doesn’t mean we close up shop when the sun goes down.

For 15 years now, I’ve been roaming around Southwest Florida as a reporter and editor searching high and low for a good time. And I’ve found that whether your idea of a good time is sipping a well-crafted cocktail, seeing a hot local band or enjoying a girls’ night out on the town, there is something everyone will love close at hand.

Oh I, I love the nightlife. I got to boogie. —Alicia Bridges

W hile the rest of the world has succumbed to the joys of packing too many people onto a too-small dancefloor and filling them with drinks and a healthy dose of lust, Southwest Florida—and Naples, in particular—has remained mostly immune. There have been many a failed attempt at creating some sort of Miami-meets-Las Vegas den of pulsing electronic music and bottle service. To list them here would be to recall names of businesses that were forgotten almost as soon as they were constructed.

But Mercato in Naples came along and changed the game. With a mix of venues in a contained geographic area, Mercato’s developers hit upon the perfect nightlife alchemy—a place where old and young, men and women can find something that works.

And at the epicenter of it all is Blue Martini. Turns out the right mix for a nightclub in Naples is a live band in the early evening for an older crowd and DJs for the younger folks later. In the middle is a combustible blend of older men and younger women and stiff drinks that might border on lecherous.

If dancing or thumping music isn’t your jam, you have other options. Burn by Rocky Patel keeps the music loud and the drinks strong but trades the dance floor for a humidor—stocked with Rocky’s famous smokes and more.

Cavo Lounge is more chill, with pianos and guitars taking the place of DJs. The Wine Loft offers a more refined version of your local watering hole. The Pub at Mercato can get a little raucous, but it has a cerebral side (see our sidebar for more).

Word of caution to the fellas: If you don’t know your full itinerary at Mercato, be sure to wear a collared shirt and closed-toe shoes. Otherwise, your options diminish as the evening wears on.

I like the nightlife, baby. … Let’s go! —The Cars

F or folks living south of Estero, visiting downtown Fort Myers is practically akin to visiting a foreign country. And as such, it deserves to be explored carefully to suss out the local customs. Whereas downtown Naples’ idea of diversity is mixing Italian, French and seafood restaurants on the same street, downtown Fort Myers begs you to pop into alleyways and look behind doors.

That’s how you’ll stumble into one of the best bars in the area—Space 39. Slide past the lion-head fountains that give Patio de Leon its name and dive into the small but vibrant bar located in the former ticket office of long-since-destroyed, turn-of-the-century vaudeville theater everyone in town called “The Ritz.” A live band will be playing soul or jazz or funk. Friendly bartenders will be pouring well-crafted drinks.

You don’t need to memorize a special knock or be given today’s password to get into the 86 Room, just a few doors down from Space 39, but the speakeasy vibe will make you feel like someone in-the-know. And a few blocks down on Bay Street, you’ll find the Barrel Room, with local and regional bands good enough that you don’t mind forking over $5-10 for a cover charge (pretty much unheard of in our area).

The refurbishment of the downtown Fort Myers area over the past 15 years has led to a remarkable transformation that has made it the epicenter for nightly happenings. The famed Art Walk got so popular it spawned Music Walk and now Mystery Walk (which turns bar hopping into history-based scavenger hunts). To get the best experience, truly make a night of it by starting with a Friday night walk, and following it with dinner and drinking into the early morning.

The nightlife ain’t no good life, but it’s my life. —Willie Nelson

C ruising down Fort Myers Beach recently with the top down on my convertible, I was flooded with memories of my first few years in Southwest Florida. None of them were appropriate to share with my 15-year-old “Little Brother” in the car. Big Brothers Big Sisters regulations prohibit imbibing of any sort in the presence of your Little, so telling booze-fueled stories of my misspent 20s seemed like crossing a line.

For anyone who has spent a considerable portion of their formative young adult years in Southwest Florida, Fort Myers Beach nightlife is a rite of passage. That goes doubly for Midwesterners who spent their college spring breaks doing something other than soaking up sun and chasing co-eds. There’s something magical about working up a sweat to an amazing reggae band at the Lani Kai or guzzling tiki drinks at the Junkanoo before the worries of mortgages and kids come into play.

The amazing thing about Fort Myers Beach is that you can live that life, even if just for a few hours or days, no matter how old you are. No one is going to give you side eye for deciding 11 a.m. is really when the nightlife starts today. And it’s the only place in Southwest Florida where you can drink with your toes in the sand without being a guest at a hotel.

Don’t set an itinerary. Don’t make a point to hit any place in particular. Just start out at Times Square and start making your way south. The best approach here is to let the evening take you where you need to go.

Sure, you might hear a few more Jimmy Buffett tunes than we would normally recommend. Yes, you will certainly feel a bit of pain the next day, either from your throbbing head from too many rum runners or your throbbing feet from thinking dancing until 2 a.m. was a good idea. Thankfully, though, you no longer need to go to Waffle House to sober up because Uber will make sure you get home fine.

Related: The Best Spots ...