12 Best Estero Wine Shops & Bars for When You Need a Night Out on the Town

Pezzo Pizza + Bar is not your average Estero hangout spot. In fact, everyone in Southwest Florida considers it a hot spot. The moody ambiance and natural stone bar, with built-in color-changing LED lights, make it a favorite for anyone looking to forget that they’re in Estero proper.

Try some of their creative cocktails like The Glitter Mafia and Tiramisu Old Fashion. I’m sure I don’t need to convince you.

As far as I’m concerned, Oak & Stone has two major perks. First off, there’s a self-serve beer wall with anywhere from 40-60 brews on tap. For someone like me, who likes to sample a beer first, this is pure heaven.

Secondly, their outdoor patio is lush. You can actually forget you’re hanging out in a strip mall. For those of you new to Southwest Florida, you’ll soon learn that everything is in a strip mall — and not all of them are pretty.

So technically, Backyard Social is in Fort Myers. But the intersection of Ben Hill Griffen and Alico is close enough for me.

Backyard Social is the place to go with a big group of friends. There’s live music, duck pin bowling, shuffleboard, and more. There’s also great signature cocktails, so make sure you visit one of the food trucks beforehand.

Put on a cocktail dress and sports coat (or a collared shirt if you’re like my husband who ditched the office clothes when we moved down south), and grab a seat at the bar.

Enjoy a glass of wine (or the whole bottle), a craft cocktail, or digestivo at this classy joint that feels straight out of 1920s New York — but without the snowstorms.

So as of November 2024, the good folks at R.A.D. Winery are still waiting on their permits. Once those are approved, we’ll have our first winery and farm fueled by passion and dragon fruit.

In addition to sipping on one-of-a-kind wines and listening to live music, you can rent out a raised garden bed and try out your hand at gardening. Of course, I could kill a cactus — so you’ll just find me checking out the food trucks and asking for another glass of Estero’s finest.

Yes, there’s a full-service bar; but people come for the 16 bowling lanes, billiards tables, sports simulators, and axe throwing lanes.

What’s so great about this place is its versatility. Bring your kids — or ditch ’em and opt for a night out with just the adults. After all, there is a full-service bar.

This place gets packed — and for good reason. Some of their accolades include “Best Happy Hour,” “Best Raw Bar,” “Best Place to Hang With the Locals,” and more.

People love the music, the chicken wings, the service, trivia nights, and lively atmosphere. Plus, you can always count on the game being on. Excuse me while I send my husband off to watch the Packers game.

Finally, for a bar that exudes everything you would expect to find in Southwest Florida. Brought to you by Tommy Bahama, the Coconut Point Marlin Bar is a laidback oasis with a walk-up bar and outdoor patio.

The building’s pink facade paired with its fun and fruity cocktails make it a great spot for a casual afternoon. Even better, you can sit outside on the hottest day of the summer and still feel cool from the overhead misters.

This is the place where I send my husband and all his guy friends to wine and dine without me. But rest assured, plenty of ladies love this spot too.

In addition to a versatile menu, you’ll find the game on one of 80 TVs. Between that and the athletic décor, you might say this is a serious sports bar.

Looking for an ice-cold drink without the hangover? Mocktail lovers will adore Kava Culture for its botanical infusions derived from the kava root. According to Wikipedia, the root produces euphoriant qualities — which is definitely more than I can say for a Bud Lite.

Because this unique stomping ground is located in Miromar Outlets, you can also use that all-natural high to fuel your next shopping trip. Talk about a win.