The key to getting the most out of 3 days in Pensacola? Listen to the locals.
I won’t lie — my first thoughts when envisioning a 3-day trip to Pensacola were of overcrowded beaches, tourist trap restaurants anchored by giant crustaceans, and sugary tropical drinks destined to leave me with a hangover. But a recent weekend proved just how wrong I was.
Tucked away (but not too far) from the beaches, downtown Pensacola is a hidden gem. A haven of small-town Florida living, the compact downtown district is home to a quintessential main drag (Palafox Street), independent retailers, small-batch producers, and delightful foodie finds just waiting to be discovered. Ready to explore? Pack your bags and get ready to let your hair down, relax, and have a little bit of fun. This is your guide to spending 3 perfect days in Pensacola.
How to Spend 3 Days in Pensacola
- Where to Stay
- Thursday
- Friday
- Saturday
- Sunday
Where to Stay in Pensacola
First things first: You’ll need a place to rest your head. While the Pensacola Beach side of the bridge offers plenty of watefront opions, I’d highly recommend staying closer to downtown in a boutique retreat away from the crowds.
Enter Lily Hall. This newly opened retreat in Pensacola’s Old East Hill neighborhood is a design-lover’s dream with vintage-inspired tilework, rich jewel-toned walls, and functioning record players in every room. The hotel only has 15 rooms, ensuring that it never feels crowded. An upscale Spanish restaurant (Brother Fox) and speakeasy (Sister Hen) add to the elevated experience.
Your 3-Day Pensacola Itinerary
Thursday Lunch
Once you arrive in town, head straight to the historic Sacred Heart Hospital. No, you’re not here for a physical, but you are about to indulge in some self-care. This former hospital-turned-retail space is home to A Mano Panino, a Tuscan-style sandwich shop with gourmet flair.
Husband and wife team Alex and Ashley Lamonte craft their Italian panino on scratch-baked schiacciata bread, piled high with authentic ingredients like herb-roasted porchetta, porchini and pecorino spread, and kale and pistachio pesto. Grab a sandwich to go or enjoy it on the breezy patio. Either way, be sure to stop by Lamonte Gelato for dessert before you leave.
Thursday Afternoon
After lunch, make your way to Alga Beer Co. for a locally brewed pint. If cocktails are more your speed, then pop to The Florida Room next door for happy hour. This unique neon-hued spot is a Miami Vice fever dream inspired by 1980s Florida kitsch. But what makes The Florida Room truly unique is its seltzer-focused menu.
The state’s only seltzer bar was an invention of necessity, due to Florida’s notoriously tricky liquor license laws. To get around the red tape, co-founder and brewmaster Brett Reid decided to brew his own seltzer flavored to taste like classic spirits. The result? A low-ABV menu that’s perfect for sipping after a long day spent in the sun. Be sure to order one of the spiked slushies for an extra refreshing treat.
Thursday Dinner
Take it easy on your first night in Pensacola and enjoy the fact that one of the city’s best new restaurants is just steps from your bed. Lily Hall’s signature restaurant, Brother Fox, is a modern Spanish spot specializing in flame-grilled fare. Start with a gorgeous grazing board and a glass of Albariño before digging into the signature Prime Skirt Steak Asada for two (or more). End on a sweet note with housemade churros and salted caramel dipping sauce.
If you’re not quite ready to call it a night, head around the side of Lily Hall to the red phone booth. Pick up the phone and wait for the door to Pensacola’s first-ever speakeasy to swing open. Step inside the moody, candlit ambiance of Sister Hen and get ready for a beautifuly crafted nightcap. Locals rave about the Banh Mi Tini, a Vietnamese twist on the dirty martini with cilantro, cucumber, white balsamic, and a squeeze of lime.
Friday Morning
Take a few extra hours to enjoy that king-sized four-poster bed in your room at Lily Hall before venturing out for the day. Start things off with a Lotus Latte (Espresso, Peanut, Black Sesame, Ginger, Soy, Oat Milk) at Alla Prima, a local “micro-roastery” run by the ever-enterprising Summer Sevi. If you’re really into coffee, or just have a curious mind, be sure to ask her brilliant baristas about the various roasts and their unique flavor notes. Those craving the chance to dig deeper can sign up for Barista Lessons, during which you’ll learn to make the perfect espresso and even attempt your own latte art.
Friday Lunch
After all that caffeine, you’re going to need some sustenance. Enjoy an early lunch at Sake Cafe, an airy Asian restaurant housed inside a converted church. Sushi and hibachi are staples here, but the draw is the lionfish tasting. An invasive species to the Caribbean and the Gulf, lionfish are wreaking havoc on native ecosystems, but luckily, they’re also delicious. Sake Cafe does its part to help keep the Gulf beautiful by serving up lionfish prepared three ways: sashimi, sushi, and tempura-fried. Now that’s an indulgence you can feel good about.
Friday Afternoon
Fully fueled up, it’s time to explore the beachy side of Pensacola. Take a quick drive over the Pensacola Bay Bridge (aka, “The Chappie”) for an action-packed afternoon.
Explore Gulf Islands National Seashore
Perched on the western tip of Santa Rosa Island, this national park offers overnight camping, sugar-white beaches, and scenic trails that are just begging for exploration. There is a $25 fee per car to enter the park (unless you already have a national park pass), but it’s valid for seven days. In addition to the gorgeous natural setting, highlights here include historic Fort Pickens and free ranger-led walks through the spectacular terrain.
Stroll Pensacola Beach Pier
Jutting more than 1,400 feet out into the Gulf, Pensacola Beach Pier is the perfect spot for a sand-free stroll. People watch from the pier, look down to see schools of fish weaving in and out of the wooden supports, and spy fishermen hauling in local catch like king and Spanish mackerel, cobia, mahi mahi, and flounder. Just beware that the pier does have a $5 entry fee.
Walk the Pensacola Beach Boardwalk
The heart of Pensacola Beach, the boardwalk is home to all the glorious beachfront kitsch you could ever want. Browse for souviners, grab a drink at one of the many open-air bars, or simply grab an ice cream cone and stroll the boards while watching beachgoers enjoy the white sands and crystal clear waters of Santa Rosa Sound.
Friday Dinner
When you start to feel peckish, make your way to The Grand Marlin. In true barefoot luxury fashion, this Pensacola Beach institution has a very “come as you are” attitude despite the upscale ambiance and elegantly plated dishes. The restuarnt prints its menus every day to reflect the freshest catch, so obviously, seafood is a must here. Be sure to request a table on the open-air patio to enjoy a side of sunset views with your mango mojito and grouper piccata. For dessert, don’t skip the tropical gooey butter cake — it’s a beachy revelation.
Friday Night
After dinner, try your hand at something a little different with a sunset kayak excursion. Glow Paddle offers clear-bottom kayak rentals, outfitted with colored LED lights for an added dose of after-dark fun. If you’re lucky, you might see fish or stingrays swimming just beneath the surface.
Saturday Morning
Saturday mornings are for farmer’s markets and Pensacola has a great one. Taking over two different locations on either end of Palafox street, the aptly named Palafox Market is a highlight for locals and visitors alike thanks to a huge array of regional vendors. Look for everything from laser-cut wood carvings to Turkish coffee, pet paraphernalia, and Nordic pastries.
While there are plenty of options for a quick bite or cup of Joe, those who prefer to sit and sip their coffee can grab a seat at Maker’s Cafe on South Palafox Street. Seasonal ricotta toasts and gluten-free goodies provide refreshment, as does the very welcome A/C.
Saturday Afternoon
Continuing your cultural excursion of downtown Pensacola, head just a few blocks over to Jefferson Street to discover a blast from the past. Historic Pensacola Village is a strollable 8-acre site encompasing nearly 30 historic buildings, 11 of which are open to the public. Simply grab a ticket online or at the musuem desk ($12 for adults, cheaper for kids, seniors, military, and AAA members) to enjoy access to the site for a full seven days.
Included with the price of admission is a tour of the site led by a costumed guide, as well as access to the Musuem of History, Children’s Musuem, Musuem of Art, and the Museum of Industry. Explore as much or as little as you want — there’s also a tea house and a brewery tucked into the historic district if you need a little break.
For those looking for an even deeper dive into Pensacola’s history, be sure to look for stops along the America’s First Settlement Trail. This free, three-mile-long marked path through downtown Pensacola and the Pensacola Historic District highlights 20 stops and over 70 points of interest spread over more than 260 years, all available to access via QR code.
Saturday Dinner
With all that exploration under your belt, you’re probably more than ready for a hearty meal. Come dinnertime, stop into The District: Seville Steak and Seafood, a historic Pensacola steakhouse housed in a 130-year-old building. This upscale spot specializes in dry-aged steaks, though the District Onion Soup and Oysters Rockefeller are both equally noteworthy.
Saturday Night
Keep the classy vibes going after dinner with a stroll down Palafox Street to The Kennedy. This retro-inspired lounge specializes in martinis and Asian-inspired small plates, all enjoyed beneath the shimmer of a disco ball. The velvety espresso martini is a must-try, though you can’t go wrong with any of the signature creations.
If you’re looking to extend your evening a little longer, make your way back towards The District to check out the adjancent Seville Quarter. Pensacola’s nightlife destination since 1967, this unique after-hours spot is like a little neighborhood of unique watering holes — think a food hall, but with bars. Start your night at Rosie O’Grady’s (the flagship bar) before hopping around to other quirky spots like Fast Eddie’s, End O’ The Alley Bar, and Apple Annie’s. Once you’ve hit your limit, simply catch a ride back to Lily Hall for a well-deserved night’s sleep.
Sunday Morning
Take your time getting up before heading back to Palafox Street for coffee and a quick breakfast. Check out Parlor Doughnuts for over-the-top breakfast pastries (vegan and gluten-free options available) as well as breakfast tacos and a surprisingly delicious sausage biscuit with fig jam. Or, head to Fosko Coffee Barre for artisan coffees and crepes.
Sunday Afternoon
Pack up the car and head to the beach. Pensacola offers around 10 public beach access points, plus an additional 8 on Perdido Key. For the best chance of escaping the crowds of Casino Beach, use that handy-dandy national park pass that you bought earlier this weekend to explore Gulf Islands National Seashore and head for the quiet shores of Langdon Beach. A favorite with locals, this off-the-beaten track beach access point offers a covered picnic area with bathrooms, plus a long stretch of soft white sand that makes it easy to find a quiet perch all to yourself. Set up an umbrella and a beach chair, slather on some SPF, and enjoy those Gulf Shores rays.
Sunday Night
To cap off your 3 days in Pensacola, you have to have dinner at a rowdy seafood restaurant on Pensacola Beach. With live music and a full bar, Flounder’s Chowder House (I dare you not to say it with a Boston accent) fits the bill. Grab a basket of fried pickles and a cold beer, and enjoy tunes from local bands on the outdoor patio as the Gulf breezes keep you cool. It’s kitschy, but in the way only a beach town can get away with.