Vacation Artfully in Pensacola

Nestled in the Sunshine State’s Emerald Coast is the one-of-a-kind beach metropolis of Pensacola. While perhaps best known for its sugary white sand beaches, the “Festival City of the South” is home to a thriving arts scene that allows visitors to travel vibrantly.

Sid Williams-Heath, Executive Director of the Pensacola Little Theatre, is a key figure in the city’s arts spaces. “Pensacola is somewhere you can truly sink your teeth into — in addition to sinking your toes into the sand,” he gushes. In other words, vacationers may come for the beach, but they stay for so much more.

To help you plan your trip, we talked to Sid about everything to eat, drink, see, and do in Pensacola. Check out his guide below.

“My mother always told me I had a knack for stirring up drama,” Sid jokes. “So it was only natural that I would find myself running a theatre.” If you, like Sid, enjoy live performances, he recommends checking out the production schedules at the Saenger Theatre, Vinyl Music Hall, and the Clark Family Cultural Center ahead of your trip to see who’s playing — including comedians, musicians, and other performers — while you’re in town.

Alternatively, take advantage of Pensacola’s legendary beaches with a dolphin cruise and sailing excursions, or stay on land and experience the city’s strollability. Says Sid, “We don’t walk, we stroll.” If you’re looking for a little more action, Downtown Pensacola features myriad activities, hip bars, and boutiques, making it the perfect place to head to on a whim, for people from all walks of life.

Before you dive into a bustling Pensacola itinerary, though, you’ll need to fuel up. Thankfully, there are a variety of dining options for any palate or vibe; Sid shared some of his favorites with T+L. 

For a quick bite, Bodacious Cafe’s wide selection of acai bowls, breakfast wraps, sandwiches, and quiches are your best bet. Got a little more time? Stop in to Native Cafe for a homestyle, sit-down breakfast; they serve their entire menu all day, so there’s no need to worry about rushing out the door in the morning. If you’ve got just enough time to grab some caffeine, The Nest Coffee Bar has you covered in the form of lattes, Americanos, chais, matchas, Vietnamese iced coffees, and more.

When midday hunger hits, you have your choice of cuisines, from The Grand Marlin’s ultra-fresh seafood (they print their menus daily) to Carmen’s Lunch Bar’s multicultural dishes to George Bistro + Bar’s South-meets-South (that’s the South of France and the Southern United States) menu. 

After a long day of exploring all that Pensacola has to offer, sit down and relax into an elevated dining experience. With an eclectic selection of staples like a ribeye and cheeseburger to distinctive seafood dishes like lump crab ceviche and smoked tuna dip, Dharma Blue Cafe is sure to keep everyone happy. For a more adult meal, Restaurant Iron offers a mouth-watering selection of ethically sourced prime beef, while Angelena’s Ristorante Italiano makes pizza, pasta, and vino dreams come true.

Whether you’re seeking a nightcap, a happy hour, or a stop on your bar crawl, Pensacola’s lively bars and lounges provide great drinks and a great time. The Well Floridian Lounge is sure to be an instant hit for any beer lovers in your party. Those seeking innovative cocktails will want to stop by The Kennedy Bar, which features classic, mid-century cocktails with a modern twist, as well as their nearby sister establishment, Old Hickory Whiskey Bar.

No Pensacola trip is complete without a visit to Sandshaker, home of the “original” Bushwacker, a creamy, chocolaty, blended concoction that can be served with or without rum. Sid’s advice? “Get a fresh banana blended into your Bushwacker — trust me.” 

Non-drinkers can enjoy cold-pressed juices, wellness shots, and nut milks, as well as delicious smoothies and a selection of coffee shop classics, from The Daily Squeeze.

“We all know that day of vacation – perhaps the forecast includes an afternoon of rain, or your kids are simply feeling beached out,” Sid notes. “They can be some of the worst days of a trip. But in Pensacola, with so much to experience beyond the beach, they become some of the best.”

Sports fans of all ages can catch the Pensacola Blue Wahoos at a minor league baseball game; families with kids can play with science and stuff at the Mess Hall, or zip-line through Adventures Unlimited. Couples can slurp down oysters at Peg Leg Pete’s, then get dolled up to roam the town on Gallery Night or hit the dance floor in Seville Quarter, and drag on the night into The Cabaret. 

“There is something for anyone and everyone in Pensacola,” says Sid. “Pensacola Beach is just the beginning.”