How to Spend a Long Weekend in Pensacola

About two minutes into a sunset sailboat cruise, I found myself wondering, “Why in the world haven’t I been to Pensacola Beach before?” Listen, I’ve never met a beach I didn’t like, (well, maybe that one time in Nice, but I digress), so I couldn’t believe I’d let the sugary-white sand of Pensacola Beach, fall off my radar. Especially when it’s only five and a half hours away from Huntsville!

And while the pristine beaches and cotton candy-colored sunsets would be enough to entice anyone down to Pensacola, there’s way more to this sun-kissed coastal town than just a pretty face. Lucky for me, I had a few days to get to know Pensacola a little better, so I thought I’d share it with you… you know, just in case you decide to get acquainted, too, which I absolutely think you should.

Thanks to Visit Pensacola for hosting us!

Day 1 in Pensacola Beach

My first day in Pensacola wasn’t actually a full one, but our brief introduction was no less impressive than if I’d had the whole day to explore. Let’s start with where I stayed – the Hilton Pensacola Beach Gulf Front. This family-friendly location has spacious one, two, and three bedroom suites, some with a kitchenette and/or children’s bunk beds for those who want the perks of say, a condo, but the convenience that a hotel has to offer.

Pensacola Hilton

My beautiful Gulfside room boasted a private balcony, overlooking the beach, two outdoor pools, and a children’s play area. Oh, and did I mention there’s also a third indoor pool, beachfront pool deck, and private cabanas for rent? And with three different on-site restaurants to choose from, I could have easily spent a whole day just hanging out at the hotel.

Personally, I have to say the thing I most enjoyed about my hotel stay (other than the view), were the unexpected touches, like the ability to hotel hop to the two neighboring properties, and that free tequila tasting in the lobby on the evening of my arrival. (Mmm-hmm.)

Pensacola Florida

Now back to that sunset cruise, courtesy of Gulf Breeze Sailing, which pretty much set the tone for my entire trip. My fellow crewmates and I enjoyed a one and a half hour relaxing, picturesque sail in the Pensacola Bay, while learning about the variety the city has to offer. FYI, Gulf Breeze Sailing also offers full and half-day sails, perfect for a cozy couples trip.

Next up was a delicious meal at Casino Beach Bar and Grill, located right off the Pensacola Beach Pier, another perfect spot to catch those gorgeous sunsets, by the way. I couldn’t get enough of the Ahi Tuna Nachos, and their lobster club sandwich is truly something special.

Casino Beach Bar & Grill

FUN FACT: If you’re dining at night by the beach and find the lighting a little dimmer than you’d like, it’s because the restaurant reduces the artificial lighting in the summer so as not to disturb nesting sea turtles and hatchlings. Good food and good conservationists!

After dinner, it was back to the hotel for a good night’s rest and a little research for the next day’s adventure.

Day 2 in Pensacola Beach

The next day, I set my sights on the 150 year-old Pensacola Lighthouse, where I climbed its 177 steps to witness a breathtaking view of the Pensacola Pass. I’m told that view becomes even more spectacular on Tuesdays and Thursdays when the Blue Angels can be seen practicing their famous maneuvers, but reservations are required for those days, so plan ahead.

QUICK TIP: Skip the flip flops on this visit, unless you want to climb those stairs barefoot, (like I did), per Coast Guard rules.

Pensacola Lighthouse

There’s also a small Maritime Museum on the property where you can learn more about the history of the lighthouse and its keepers, and perhaps even have a ghostly encounter. In fact, the Travel Channel and Sci-Fi’s Ghost Hunters claim it’s one of the most haunted lighthouses in America; and the gift store clerk had quite a story to share with me about her own experience with some unexpected visitors.

Across the street from the lighthouse is the National Naval Aviation Museum, a must-see, especially if you have any air and space enthusiasts in your household. It’s a stunning structure is with its seven-story glass atrium, but your kids will probably be most impressed with the full motion simulators, giant screen theater, and of course, the beautifully restored and replicas of aircraft. I barely scratched the surface of this 350,000 square foot museum, so you and your family could easily spend your entire day here.

National Naval Aviation Museum Pensacola

Even though there’s also a cool cafe on site that doubles as a museum exhibit, I decided to head downtown for a bite to eat at Jaco’s Bayfront Bar & Grille. Jaco’s sits at the end of Palafox Pier and right outside is the Plaza De Luna Splash Pad. Named for Pensacola’s founder, Don Tristan de Luna, it’s a great place for the kids to cool off after a day of activities or a stroll down Palafox Street.

Speaking of which, Palafox, named one of America’s top 10 streets, has a little something for everyone, including restaurants, boutiques, and some pretty swanky galleries. Since I was eager to get in some beach time, though, I decided to save the full Palafox experience for later, and drove over to historic Belmont-Devilliers. Here’s where you’ll find outdoor murals that pay homage to Pensacola’s historically black business neighborhood, as well as the famous Five Sisters Blues Cafe, home to what many of the locals say are the best collard greens in the city.

Palafox Street Pensacola

After enjoying the sunset on the beach, and a quick change of clothes, I headed back down to Palafox Street to check out the nightlife, where I quickly discovered that I was a lot more tired from the day’s events than I thought. So, I did some quick recon of the shops I wanted to visit the next day, and made note of a few places like Blend Lounge, which should definitely be on your list if you’re considering Pensacola for a girls’ (or guys’) trip.

Day 3 in Pensacola Beach

The forecast called for rain on my last day in town, so I thought it would be the perfect time to visit a couple more museums, and do a little shopping before hitting the road.

In honor of my favorite artist (my daughter), I popped into the Pensacola Museum of Art, housed in a two-story Spanish Revival style building that actually used to be the city jail. And just a few blocks away is the T.T. Wentworth, Jr. Florida State Museum, former site of City Hall.

Featuring artifacts and exhibits that highlight Florida’s rich heritage, the Wentworth museum is one of several others in Historic Pensacola Village that history buffs will love. My favorite was the second floor exhibit which featured a replica of Trader Jon’s, a former popular tourist destination where folks from all walks of life gathered, and military memorabilia was sometimes traded for drinks, giving rise to what native Pensacolans know as “Tradernomics.”

Historic Pensacola

Finally, I rounded out my visit with a final stroll down Palafox Street to pick up some luxurious but wallet-friendly, handmade bath and body products from Belle Ame’ and gorgeous accessories from Indigeaux Denim Bar & Boutique, as gifts for my favorite people back home.

But I absolutely could not leave without stopping by Bubba’s Sweet Spot, which is covered in handmade candy, including some of those old-school favorites we know and love. And I dare you to try and get out of there without sampling some of their homemade ice cream. Needless to say, this place is a treat for the whole family, much like Pensacola Beach itself.

Pensacola Perdido key FL

As you can see, I packed quite a bit into my little trip, but there’s so much more to do and see. That’s why I’m planning another visit with my daughter later this summer, with a few more items on the list, including Wahoos Stadium, where ballpark food takes a gourmet turn; Big Lagoon State Park, where nature lovers will feel right at home; and Graffiti Bridge, where street art puts on a daily show.

So here’s hoping I’ve piqued your interest, and if so, let me know and I’ll meet ya at the beach.

Visit Pensacola FloridaHuge thanks to Visit Pensacola for hosting Rocket City Mom as part of their southern #PcolaPressTrip in Pensacola Beach, Florida. While travel & lodging were provided by Visit Pensacola, opinions expressed here are 100% our own.

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