Florida is the top vacation destination no matter the time of year! While we normally think of the sun and sand as a summer affair, Florida is just as beautiful in the late winter and spring. I took a February trip to Pensacola this year sponsored by Visit Pensacola, and had the chance to see a sampling of the city’s best attractions and accommodations. Here’s the perfect itinerary for a three-day Pensacola vacation!
Day 1: Diving into Music, Art, and Food
I arrived in Pensacola at midday, which left plenty of time to explore the city before turning in for the night. If possible, I highly recommend planning your itinerary to coincide with Gallery Night. This monthly street festival features live music, art vendors, and food—perfect for the whole family, date night, or, in my case, solo travel! There’s a different theme every month, so no matter when you visit Pensacola, you can always look forward to something unique. There seems to be some kind of festival and event going on regularly. I spotted Mardi Gras decorations all around the city.
At the end of the evening, I headed to Jackson’s Steakhouse for dinner. What a vibe—the décor, the service, and the people-watching were as delightful as the meal! This award-winning steakhouse is the ideal pick for a nice steak dinner, but the menu also includes locally-sourced seafood, pasta, duck, and much more. The restaurant is named for Andrew Jackson, who accepted the transfer of Florida from Spain to the United States in the plaza across the street in 1821. I was surprised to discover so much history in Pensacola!
After wrapping up at Jackson’s, it was time to get to my beautiful hotel, the Hilton Pensacola Beach. This was an incredible stay with incredible service—the beach views are simply gorgeous, room service (breakfast in bed!) was divine, and I loved being so close to shops and restaurants. You can also enjoy an indoor heated pool, spa, and fitness center. The pool area and surrounding grounds are pure oooh-la-la. It’s really giving tropical resort!!
Day 2: Exploring Downtown and Hitting the Beach
Day two started with a delicious breakfast in bed at the Hilton before heading over to Palafox Market in downtown Pensacola. This open-air dog-friendly market has numerous stalls selling fresh foods, baked goods, and flowers. There’s so much to do and see downtown, so be sure to pencil in several hours for this excursion!
After a few laps around Palafox Market, make a stop at the Pensacola Museum of History. This museum features eclectic architectural styles—everything from Victorian to French Creole. Outside the museum are the eye-catching blue trees. This ongoing installation is meant to remind us of the importance of trees in Pensacola and beyond. In addition to having a great message, this urban forest is also an excellent photo op!
Once you wrap up at the history museum, set off on America’s First Settlement Trail. This three-mile route runs through Pensacola’s stunning Historic District. Throughout the trail, you’ll find 20 stops and 70 points of interest relevant to Pensacola’s storied past. It’s the most fun and engaging way to get a crash course on the area’s history!
A few blocks away, the Bruce Beach Revitalization Project is fascinating. As part of an initiative to create more waterfront experiences in Pensacola, the Bruce Beach area was recently renovated and is a lovely area to enjoy a stroll, a coffee or picnic, or a bit of bird watching (and people watching!) if that’s your thing. The park also has informative historical markers commemorating the history of Bruce Beach as a gathering place for the Black community in the 1950’s and 60’s.
Now that you’ve had your fill of history, we have one more stop—the beach, of course! Even in February, the scenic views of the Gulf are incredible. I took a beautiful walk along Pensacola’s white sand beaches…be sure to stroll down the Pensacola Beach Pier and enjoy the amazing views!
Before we can end my second day in Pensacola, we need to talk about food! Here are two additional recommendations for this part of your Pensacola vacation:
- Jaco’s Bayfront Bar and Grille—Fresh seafood with a view of the water? Sign me up! This spot is perfect for a light lunch or a casual dinner. The calamari is some of the best I’ve ever had.
- Drift Pensacola Beach—Dinner at Drift is a luxe experience! The ambience is incredible, and the gourmet dishes can’t be beat. I loved having seafood and a mocktail while watching the sun set over the gulf.
Day 3: Visit the Iconic Maritime Museum
Day three began with the best jazz brunch I’ve experienced in a long time. The Five Sisters Blues Café’s menu is amazing, full of good old-fashioned Southern cooking. Whether you’re a connoisseur of collard greens or have never had them, this is the place to do it. So good! The band was superb. OMG! I can’t recommend this Black-owned restaurant enough for a delicious jazz brunch.
It’s my last day in Pensacola, but that doesn’t mean missing one final attraction! If you have an early afternoon flight, you’ll still have time to swing by the Pensacola Lighthouse and Maritime Museum. This cultural center is excellent, and as always, I love an old lighthouse! I climbed the 177 steep steps to reach the top, and the bird’s eye view of the water certainly did not disappoint.
And with that, my solo travel in Pensacola came to an end! I loved my weekend itinerary, but if you have more time in the city, you might also try these activities:
- Trolley rides
- Dolphin cruises
- Exploring the Gulf Islands National Seashore
- Watching a U.S. Navy Blue Angels practice
- See Visit Pensacola’s website for ideas
Spring Is Around the Corner—Book Your Pensacola Trip Soon!
Pensacola is a dream no-passport destination for my friends in the U.S.! While most think of going to Florida in the summer, the late winter brings its share of benefits, too. The cooler weather is nice, and although it was a bit rainy briefly once, nothing stops this over-60 traveler from seeing the sights! For getting here, Pensacola International Airport offers easy access and over 20 nonstop flights to the area. It’s an easy drive for those in the southeastern United States! I highly recommend you steal my weekend itinerary for a Pensacola vacation and check out the city for yourself. Head over to Visit Pensacola’s website for more tips and places to put on your schedule! No matter when you fly in, you’re sure to love this Florida getaway.
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