Coolest Block in Punta Gorda: A Nighttime Walking Tour of Downtown

By Janet K. Keeler

When the sun goes down in Punta Gorda, put on your dancing shoes. And hopefully they double as walking shoes.

From beach boogie to acoustic jams to classic rock, the compact downtown core gets an unexpected groove on as day turns to night. There’s even a spot that celebrates traditional Irish music with a side serving of punk. Why unexpected? Because about half of Punta Gorda’s 17,000 or so residents are older than 65 and that sets up certain stereotypes about sidewalks rolling up when darkness descends.

Many of those residents have fled snow and ice to settle in ranch homes and townhouses in this historic Florida riverfront town. Ah, the classic modern-day Florida retiree story that stars baby boomers collecting Social Security. Yeah, well you can count among that age group Billy Joel, Bruce Springsteen and Aretha Franklin. And they are still rocking.

Everybody, it seems, likes a good jam, especially when it comes with an umbrella drink and a sunset. That’s how we start our cool block, cool stroll experience in Punta Gorda and find people all over town busting stereotypes.

The rooftop Perch 360 at The Wyvern Hotel gets our party started (and might be where you book a night). Plop down in comfy, plush seats and watch the boats bob along the Peace River to the north. Keep your eyes trained on the western horizon to watch the sunset while you sip a classic Manhattan or another cocktail that floats your own boat. There’s not usually live music here, but it’s a fine place to see Punta Gorda from on high and plot your night.

Look south from near the rooftop pool and watch the lights of cars and motorcycles streaming up U.S. 41. The breeze portends a lovely evening. 

The yin to the Wyvern’s yang is TT’s Tiki Bar just a few minutes walk from the boutique hotel and behind the Four Points by Sheraton, another possibility for accommodations. There’s nothing fancy about TT’s but it is so Florida. Translation: shorts and sandals are the preferred attire. The thatched-roof bar sits square in the middle of the complex that hugs the seawall. Pull up an Adirondack chair around the various fire pits or get closer to the entertainment.

Music is on the menu seven nights a week at TT’s, cranking until 11 p.m. on Fridays and Saturdays. Danny Beach (perfect name, eh?) with his Hawaiian shirt and acoustic guitar is typical of the weeknight entertainment. Zombie U, Funk Fetish and Tropical Avenue pump up the crowd on weekends. There’s enough room to boogaloo (or whip & nae nae) if you are so inclined and a volleyball pit calls to the more athletic.

Florida and the tropics are on the drink menu. A frozen “Berried Treasure” mixes fresh strawberries and ice cream with light rum and amaretto. Worried about brain freeze? Order “Punta Gorda Peach Lemonade,” in which peach vodka mingles with downhome lemonade.

There’s food, too, and the menu reflects Florida’s beach bar cuisine: jerked shrimp Caesar salad, grouper sandwiches and peel-and-eat shrimp.

After the early show, we take off south for an amble a couple blocks over on Marion Street, Punta Gorda’s main drag, which is dotted with fun shops and places to grab an ice cream cone. And more music.

Punta Gorda is an old Florida town that feels new because of reconstruction and rejuvenation after Hurricane Charley made a mess of things in 2004. A direct hit damaged many old brick buildings so badly they had to be demolished. New construction has sprung up, giving the biggest city in Charlotte County new shine.  

Jacks On Marion is one of those new businesses in a new building.  The corner bistro offers indoor and outdoor seating and for our purposes, music Wednesday through Saturdays on the patio. This is the place to meet your group for conversation with light sounds in the background. The music won’t blow your ears away but it will get you swaying. Nice wine list, too. Return here for a Sunday morning bloody mary, extra spicy.

After chilling for a bit at Jacks, we head back toward the Wyvern to check out the act at Dean’s South of the Border restaurant. Its parking lot is adjacent to the Wyvern’s. Margaritas? Check. Burritos, nachos and tacos? Yes, yes, and yes. And that’s not all, as a late-night infomercial host might say. Daily blue-plate specials offer comfort food like meatloaf and goulash, and early birds can get breakfast everyday of the week. This Mexican-centric restaurant is just a little different.

Live music seven nights a week? For sure. Bands such as the Cherry Bombs and Sons of Beaches roll out classic rock late into the night on the small patio stage. It’s tight, but patrons find spots to boogie amid the four-tops laden with Frisbee-sized plates of food and chilled margarita glasses, salt or no salt is your choice. The crowd here is all about fun, and it’s a popular stop for bikers who roar up U.S. 41 on weekend rides. The Harley-Davidsons sometimes outnumber cars in the lot.   

For people watching, Dean’s South of the Border is the place to be in Punta Gorda.

Putting an emphatic period in our night was a stop at The Celtic Ray Public House. The music blasts until the wee hours on weekends, winding down earlier during the week. Patrons can hear plenty of Irish music from Cage O’Hanlon and West of Galway, but punkers Born Again Heathens and folk rockers Good Bad Kids mix it up.

As the clock ticked toward 2 a.m., we could say confidently that the Celtic Ray is where the kids hang out. There’s a full menu of British favorites like shepherd’s pie and fish & chips accompanied by Smithwick’s on draft. Dozens of beer choices, mostly U.K. favorites, can be purchased in the bottle or on draft, among them Harp, Hobgoblin and Kaliber.

From the Celtic Ray, it’s just a few blocks walk back to the Sheraton or Wyvern. Before we call it a night, something on the schedule catches our eye and encourages a return trip: Tuesday Trivia.

Best place for live music in Charlotte County you ask? The winning answer is walkable downtown Punta Gorda.