While the sugar-white sand might be the first thing that attracts you to Pensacola, this Panhandle city is more than just another sunbathe-all-day beach town. The historic downtown — home to a number of museums — reveals why Pensacola became known as The City of Five Flags.
Plus, it’s easy to explore the best of what modern Pensacola has to offer, from fine-dining to food trucks. Of course, you’ll want to spend plenty of time in and around the city’s deep green waters as well.
Pensacola Beach is coastal living at its best, with water sports and eco-trails to help you enjoy the 300 annual days of sunshine. You’re bound to leave with a belly full of seafood, a local history lesson and a beachy glow.
As always, check for travel restrictions and closures before planning your trip.
Friday: Visit The Historic Downtown
Today is all about exploring Downtown Pensacola. Start with a signature omelet at Ruby Slipper Cafe to fuel up before heading to a couple of museums.
A good first pick is Historic Pensacola Village, where you can find regular tours digging into the history of the city and its ownership (fun fact: the Spanish, French, British, Confederate and American flags have all flown over Pensacola). Here you’ll see both Spanish and British forts, as well as historic homes.
For lunch, check out the food trucks located along North Palafox Street, a main drag that’s always thrumming with activity. Tex-Mex-style Calavera Tacos and chef-driven Two Birds Street Food are local favorites — but you can’t go wrong at any truck with a lengthy line
Next, head to the Pensacola Museum of Art, which focuses on modern and contemporary art spanning from the 19th century to the present. If the kids are in tow, swap the art museum for the Pensacola Children’s Museum or Pensacola MESS Hall — an interactive museum focused on hands-on science experiments and activities.
Thankfully the downtown was designed as a walkable grid, making it easy to scope out galleries and local shops along the way.
As you head into the evening hours, set your sights on some fine dining and live music on Palafox Street. Treat yourself to a steak dinner at Jackson’s Steakhouse, a traditional spot where the side dishes rival the main course — think three-cheese macaroni with bacon, scalloped potato gratin and Florida snap beans.
End the night at Seville Quarter, where there are seven themed rooms, including a pool hall and sing-along dueling piano show that keep the energy flowing.
Saturday: Indulge in Fashion, Fish and Fun
After a busy first day, ease into your second morning. Visit Egg Wits for a surf and turf Benedict or a goat cheese omelet. From here, head to North Pensacola. More of a local neighborhood than a tourist attraction, this will give you a sense of true Pensacola living. Make your way to the Edward Ball Nature
Trail for a leisurely half-mile stroll through the hardwood swamp of Thompson’s Bayou. Keep your eye out for colorful birds.
If everyone is up for it, extend the walk by hiking with one of the many U.W.F. West Campus trail loops (the White Loop is 8.5 miles, the Red Loop is 10 miles and the Blue Loop is 12). Pack a picnic and find a spot under an old cypress tree.
If you’re skipping the picnic, get in the car and check out the rustic pub Goat Lips Chew and Brewhouse — there’s a great list of local beers on tap.
Depending on what’s happening while you’re in town, you have two choices after lunch: visit the Cordova Mall for some shopping — the mall has big-name stores and always-welcome AC. Or catch a race at the Five Flags Speedway, which has something going on pretty much every weekend. If you really want to pack the day, take on both: the two spots are just 10 miles from each other.
Toast the night with dinner at Cracking Crab Seafood Restaurant & Bar, located in the mall, or True Grit American Bistro on Nine Mile Road. The first serves up fresh Cajun seafood, while the latter is known for its build-your-own-plate, home-cooked menu items. Some motivation for the creative: You can make a mac-n-cheese steak sandwich with Buffalo sauce on top if you want.
And if you still have some energy after the busy day, end the night at Pensacola’s only amusement park: Sam’s Fun City. Choose from 20 rides and plenty of games before heading back to the hotel for a well-deserved night’s sleep.
Sunday: Take in The Sunshine
Obviously, you can’t make the trip to Pensacola and not visit the beach. That’s what today is all about. Pack the car with your beach gear and grab breakfast at Native Restaurant on the city’s barrier island. Locals consider it the best breakfast spot for fueling up for a day on the water. From here, make the 10-mile drive to Opal Beach for a stunning stretch of sand.
Take a dip in the water and nap on the beach before grabbing a bite. While it is an ideal spot for a picnic, you could also head back toward the island entrance and spend the afternoon at the Pensacola Beach Boardwalk. There you’ll find plenty of flip-flop-friendly options like Shaggy’s Pensacola Beach, which is known for its seafood and frozen daiquiris.
After filling up, take a stroll along the boardwalk for some souvenirs before spending some time at the Pensacola Beach Gulf Pier.
It’s a great spot to see local wildlife (dolphins, pelicans and other seabirds), and you can try your hand at fishing, thanks to the rental gear offered at the on-site bait and tackle shop. If you need to rinse off a bit before the evening, just pop into one of the many public showers available.
But make sure you finish up in time for sunset — you’ll want to grab happy hour drinks at either Casino Beach Bar or The Dock to take in the spectacle.
And since it’s your last night, splurge on a memorable dinner at The Grand Marlin of Pensacola Beach. This restaurant’s raw bar features BBQ oysters, Gulf shrimp cocktail and oysters Rockefeller — a fitting seaside sendoff to your weekend getaway.
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