Fort Myers vs. Naples: Whose Nightlife Is Better?

Our experts sample both towns and render their verdicts.

Here in Southwest Florida we tend to stick close to home when it comes to a night out. Naples people stay in Naples. Fort Myers people stay in Fort Myers. This creates a certain rivalry between the two. You’re either a Fort Myers person or a Naples person. So that got us thinking: Putting all allegiances aside, where is the best nightlife, exactly?

We dispatched two writers to answer that question. Stephanie Davis is known as the Downtown Diva in Fort Myers. Senior Editor Justin Paprocki haunts Mercato, Third Street South and everything in between. The catch: Neither really visits the other city that often.

So, we sent the two on a night out in each city. Here’s what they found.

Naples

A night out in Naples feels a little different from a night out in a lot of other cities. After all, there aren’t that many places where you can play luxury car bingo on an otherwise low-key November night. (Lamborghini? Got it. Porsche? Got it. Bentley? Bingo!) But don’t get too wrapped up in stereotypes. Yes, there’s a lot of wealth here. Yes, it gets flaunted. But look beyond the glitz and glam and you’ll find some great little bars and eateries that will make for an excellent night out.

For our nightlife adventure, we planned on hopping around a bit in Naples. Unfortunately, the hot spots are spread fairly far apart. Alas—if you’re barhopping in Naples, best to bring a DD (or download the Uber app).

Blue Martini, Mercato

JP: We started the night at Blue Martini because of its great happy hour. It’s half off all drinks from 4-8 p.m. daily. We got there and the dinner crowd had hogged the back patio. Luckily, the bar area was fairly free. The feel is definitely lounge-like—low lighting and an extensive cocktail list. Later on, it would be crowded—which is great if you’re single and looking to mingle. Neither of us is in that particular demographic anymore, so we scooted before the band started on the stage right behind the bar.

The nice thing about Mercato is that if you’re not into the scene in one bar, another is just steps away. Burn by Rocky Patel is a cigar bar with a great cocktail menu. TAPS is a nice place for craft beer and apps. The list goes on. Just be prepared to struggle to find parking, especially in season.

SD: I’ve been to Mercato two or three times since it opened, and while I enjoy the variety, I can never completely forget the fact that, technically, I’m visiting a shopping center. Not only that, if you’ve got a million dollars (give or take), you can actually live at Mercato. It’s like a manufactured town with a parking garage. That said, if I lived there, I’d never leave. I’d wake up at noon, slip down to one of the eateries under my condo for mimosas, then get my nails done at the salon, do some shopping, then go to happy hour, dinner, the movies, dancing, and then get back on the elevator to go to bed. My liver and my wallet would likely take a beating, but it could be a fun change of pace. During our recent visit, Blue Martini was a fine spot to start the evening, and since it was early-ish, there was an older demographic enjoying the half-price happy hour. Even at 6 p.m., the atmosphere was festive.

Paradise Wine, Paragon Pavilion

JP: Across the way from Mercato is another burgeoning hot spot. Paradise Wine just opened a little more than a year ago and right alongside came Inca’s Kitchen and Tacos & Tequila. It’s a great spot to grab dinner at one place then a drink at another.

What makes Paradise Wine unique is its setup. It’s a bar with a full-scale wine shop inside. Pick out a wine and the bartender will open it for you without a corkage fee. The vibe is laid-back. Most people were gathered outside this night, relaxing on the comfy sofas and chairs. Inside, The Mark Vee Band was playing and couples were up dancing. We chose to sit outside at the bar for a glass of wine but could have easily grabbed a table inside to watch the festivities.

SD: Not only can you drink, you can shop for wine, beer and liquor—Paradise Wine sounded like paradise, indeed! This was my first visit, and although it too was in a shopping center/strip mall, I warmed to it fairly fast. I found more variety in the clientele than at Blue Martini—I saw a couple with a stroller, some more mature folks, some younger ladies enjoying a girl’s night out. Paradise Wine felt like the perfect little neighborhood wine bar—plus, the menu featuring small plates looked yummy.

RipTide Brewing, 987 Third Ave. N.

JP: Southwest Florida is experiencing a craft beer boom. By our count, there are 16 craft breweries in Lee and Collier counties. RipTide, tucked off a side street in Naples, opened a little more than a year ago. You’d probably pass it on your way to Third Street South or Fifth Avenue South. But our photographer for the evening, Reagan Rule, suggested we give it a shot. It was a great surprise. Walk in and the first thing you notice (aside from the large silver drums used for brewing) is the crowd. It’s a young crowd. And that’s not “Naples young” (meaning 40s and 50s) but “young young” (meaning 20s and 30s). I got a 16-ounce glass of the Rip Tide Paddlepuss Blonde Ale. Not only refreshing, it was also only $5. A steal. After some time at the bar, we wandered out back and watched a game of cornhole under the clear night sky.

SD: We found the millennials of Naples—and they’re at RipTide Brewing (also in a strip mall, sigh). Finally, man buns and handlebar mustaches—a nice change of scenery. I’m not a beer drinker (like, ever), so the bartender asked me if I like coffee—which I do—so she hooked me up with a glass of their house-brewed “Totch” Brown, which tasted like a chocolate/coffee milkshake. It was not only delicious but also kept me from ordering a very unhip Diet Coke. RipTide was a bit brightly lit for my tastes, but when you’re in your 20s, lighting isn’t something to be overly concerned with. I’ll bet this place will be hopping (Get it? I know, I’m old) around spring break.

Bar Tulia, 462 Fifth Ave. S.

JP: No trip to experience nightlife in Naples is complete without a walk along Fifth Avenue South. So many bars, so little time. Usually, streets are packed with locals and tourists popping in and out of establishments or grabbing a drink on the outdoor patios. We ended up in Bar Tulia, which has a great reputation for cocktails. I had the Basilica—bourbon, Aperol, Carpano Antica with a burnt orange peel. I usually don’t go for orange-y flavors, but this one was rich and smooth and hit the spot.

The room itself is small and narrow, but featured a good energy. Young and old, lots of couples and small groups of friends. Some were eating, but this is the type of place I’d go for a cocktail after dinner—perhaps at the neighboring Osteria Tulia.

SD: I’m a big fan of Fifth Avenue South and sometimes wish there were a high-speed train that could transport me from downtown Fort Myers to downtown Naples for variety’s sake. I do love the twinkly lights, the shiny cars and the chance of stumbling onto a fashion shoot for a glossy magazine. Fifth is posh—and most refreshing of all, there are no strip malls. Bar Tulia was a delight—filled to the brim with folks of all ages chatting, laughing, eating and drinking. And speaking of drinks, cocktails are truly an art at Bar Tulia. The bar menu was fancy/rustic/hip—think fried pig ears, Wisconsin cheese curds and octopus carpaccio. Me? I went for a nice, normal cheese pizza.

Final thoughts

SD: I’ve ventured to Naples for nightlife a handful of times over the years, and every time I do, it’s like going to a different country. It’s definitely a tale of two cities; just an hour apart, but socially so different. But, I don’t mean that like it’s a bad thing. I think most of us feel at our comfiest when we’re wining and dining close to home in our own neighborhoods, where we’ll likely run into friends and the bartender knows our name. In Naples, unless you stick to Mercato or Fifth Avenue South or Third Street South, you’re going to end up driving around. So if, like me, that is decidedly not your thing, I recommend getting a hotel for the night and making a mini-weekend of Naples nightlife. And if you intend to drink (especially those deliciously strong mixes at Bar Tulia), cab it or Uber it—that way, you can relax and enjoy all the variety that Naples has to offer.

Fort Myers

There was a time—not so long ago—when downtown Fort Myers was so dull that you could practically see tumbleweeds blowing down First Street. In the mid-’90s, there were a couple of dive bars, two or three restaurants that catered to lawyers who lunch, very limited retail space and barely a pinch of culture. For most folks in Lee County, the only reason to venture downtown was for a court appearance, and that’s rarely a positive experience. But, it all changed in the late ’90s and early 2000s, when developers and entrepreneurs saw potential in some of the 100-year-old buildings, Florida Repertory Theatre made its home in the Arcade, and the City of Fort Myers invested in beautifying the River District. These days, there’s a sparkling nightlife scene that draws the happy-hour crowds and the late-night revelers. Friday nights are particularly festive, as each Friday of the month is an event—Art Walk, Music Walk, Mystery Walk and even Pet Walk (basically happy hour for dogs). Keep in mind, though, on most Friday nights, some streets in the neighborhood are blocked off for bands and vendors, so parking can be a hassle. So, we met outside of downtown and took the free River District trolley (score one for Fort Myers—public transportation).

The Bacchus Room at Prime De Leon, 33 Patio De Leon

SD: When the owners of Spirits of Bacchus lost their original space at the corner of Bay and Hendry streets last summer, most thought it would be the end to one of downtown’s longtime favorite watering holes. But you can’t keep a good bar down, so with the same employees and Cheers-like atmosphere, it moved up to the second floor of the Prime De Leon restaurant. With a cozy inside bar and an expansive outdoor balcony bar, it offers the perfect views for people-watching or enjoying a band playing in the patio. It was so busy on the balcony the night that we were there that our biggest challenge was finding a table. Luckily, we did, and enjoyed cocktails and a great post-sunset view.

JP: This was a good place to start. The streets were starting to get crowded from Music Walk, so up top was a nice way to look down on all the festivities. Pretty nice when you can kick back on a rooftop bar and still enjoy the music from down below. Oh, and four drinks cost only $26. I do live in a state of sticker shock down in Naples when it comes to prices. Naples has its spots, but overall, I feel like a night out in Fort Myers is a better fit if you’re on a tight budget.

The Barrel Room at Twisted Vine Bistro, 2214 Bay St.

SD: We strolled through the crowds about a block away to the Sky Bar in an effort to get a view of the river, but it was packed—no place to sit and not even enough floor space to stand. So we exited stage left to the Barrel Room next door. The Barrel Room is a welcome new addition to the River District with live jazz and blues, an extensive cocktail list, and food that you can either order off the house menu or from The Twisted Vine next door. There was a $5 cover for the band, but we ventured in and enjoyed a bite to eat and cocktails in a relatively quiet atmosphere. A nice break from all the hubbub in the streets.

JP: Barrel Room was small but a great place to hear a jazz combo. The room was fairly narrow, bringing your attention to the stage. The crowd appeared to be there for the show. There was some small talk, but it didn’t drown out the band. By the way, this was real jazz with long stretches of improvisation—not the soft R & B or Motown covers that sometimes get passed off as jazz around here.

The 86 Room, 22 Patio De Leon

SD: A visit to The 86 Room feels like stepping back in time to the Fort Myers of the 1920s with its speakeasy vibe, silent movies projected onto one wall, and vintage cocktails like the Sidecar, the Bees Knees, the Pimm’s Cup and more. A favorite of neighborhood residents, hipsters and theater folk, The 86 Room really gets going as the night wears on—an excellent spot for a tasty, old-fashioned nightcap.

JP: I sat on a piano stool and looked over a menu consisting of mint juleps, old-fashioneds and similar classics. The 86 Room went all in for the retro vibe. It could have been tacky, but I thought their attention to detail made it work—from the bartender’s throwback look to the funky chandeliers. I could have spent the evening just watching the silent movies projected high on the wall. But it’s hard to sit still in Fort Myers for that long.

World Famous Cigar Bar, 1502 Hendry St.

SD: Hoping to squeeze in one last stop, we popped into one of my favorite old haunts, the Cigar Bar, which just celebrated its 20th anniversary downtown (there are also newer locations at Gulf Coast Town Center and in Cape Coral). The bar is smoke-filled and masculine, with heavy leather furniture and animal heads mounted on the wall. The ultimate man cave, the Cigar Bar is warm and welcoming, and just as you order your drink, you realize that the last trolley runs at 11 p.m. and you’re about to turn into a pumpkin. We darted out, grabbed Reagan, and miraculously hopped on the last trolley out of downtown. As usual, a Friday night in the River District is never dull.

JP: I wish we could have spent more time here. It was a laid-back bar without a lot of stuffiness. I could imagine myself living in downtown Fort Myers and making this my neighborhood bar, as my companion for the evening once had.

Final thoughts

JP: Fort Myers does have a totally different feel compared to its neighbor down south. But that’s not Naples’ fault. Fort Myers has history behind it. It makes for a different night out when the streets are brick and the buildings have 100 years of stories in them. I enjoyed Fort Myers for its eclectic crowd and diverse bar scene. If you don’t mind a crowd, Music Walk or Art Walk would be a great time to go to really gauge what Fort Myers is all about. There’s little pretense here. I felt comfortable in just about any bar—as long as we could find seats—dressed fairly casually. In the end, it’s hard to say which is better. It just matters what your taste is—or what type of fun you’re looking to have. I live in north Naples, so either end of Southwest Florida is fairly accessible. I can easily see myself replicating this little experiment every month. With two short drives, I can have two totally different nights out. Perhaps we should consider ourselves lucky.