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Best of Pensacola


I’ve been fortunate enough to visit Pensacola just about every season of the year. Granted, it is Florida, so the weather doesn’t change too much from month to month, but still, there’s plenty to do no matter what time of year you’re in town. Pensacola has become one of those places, at least in my book, that feels like a second home. As a kid growing up, it was Ocean City, MD. We would go every summer as a family and spend a week or two visiting my aunt and uncle who lived on the beach. I don’t know if it was because we had everyone all together in one place, or because of the bustling atmosphere of the beach/boardwalk, but I fell in love with OC at an early age. I have so many great memories here, and even though about moving there permanently at one point in my life. I haven’t felt that way about a place again since Pensacola.

Again, I think I might be biased. I think much of my love for the Florabama shore (no, not the TV show) comes from the memories associated with it. For starters, my brother lives (I guess *lived, now) here, meaning every trip I’ve taken, I’ve gotten to spend some quality time with him. Huge for me, because of the seven year age difference and his constant moving around being in the military. But then there’s the crystal clear blue waters, the quaint downtown area, and the fact that once again, it’s a beach town, my favorite kind of place, the kind of place where anything goes, people walk around half-clothed, and your only worries are whether your drink is full or you need more sunscreen. There are so many great things about Pensacola, but some of my favorites include:

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Lay on the beach

I think this is the most obvious to-do if you’re visiting a beach town. AT LEAST (bare minimum) one day must be dedicated to solely laying (or sitting, or standing, your preference) on the beach, drinking a nice cold drink, reading a juicy book, or people watching. And boy let me tell you there is some people watching to be done in Pensacola. You won’t find waters much blue-er or (depending on the season) much warmer than these either, so make sure to take a dip to cool off! There’s a gorgeous public beach with free public parking right after you cross over the Bay Breeze bridge, so definitely check that out, or of course feel free to wander farther down the immense stretch of sand to find your own personal space.


Dance to some live music at the Fish House

Whether you’re looking for a bite to eat or a night out, the Fish House is a great option. Being from NY (aka deprived of sunlight/fresh air/happiness 9 months out of the year), I’m personally always looking for outdoor dining or places to get drinks, and the Fish House has an amazing deck area with plenty of room to spread out and mingle, or listen to some live music. Voted Reader’s Choice Award “Best Place to meet Friends After Work,” “Best Happy Hour,” AND “Best Ladies Night,” you can bet you’ll know where to find me. Plus, views from the deck lend for some great sunsets!

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Explore downtown Pensacola 

My parents and I spent an entire day downtown one weekend last spring. I’ve been a couple of times since, and I keep finding new cool shops/restaurants. It’s a fairly small city, so it’s easy to get around, but has a lot to offer! Some of my recommendations include the Whiskey Bar on Palafox St., Al Fresco and Rusted Arrow (THE hands down cutest home goods store, and you know I love a good home good store).The city even often closes off all of the street to host art exhibits downtown, which I’ve heard are pretty great! Most recently, I was downtown during the holiday season, and honestly, it was mesmerizing. Now it could be because in order to enjoy the scenery and outdoor decorations in New York, you have to brave frostbite, but something about everything being all lit up with palm trees in the distance and the smell of the ocean in the air makes Christmas a little bit more enjoyable. Call me crazy, but I’m not dreaming of a white Christmas over here.


Grab dinner at Jaco’s 

Finish up your exploration downtown and head right into Jaco’s, a bar and grille overlooking the bay. One of my favorite things about Pensacola is how cute and simple the design of every business is, and Jaco’s is no different. A relatively small restaurant, indoor and outdoor seating alike make for an intimate dining experience. Plus, I mean, take a look at this view. All yours for the entirety of your meal. I have reliable sources that say the ahi tuna, crab cake salad and fish tacos are delicious, and I can attest for the blackened salmon myself. One of the best parts about vacationing by the beach is the seafood, amirite?

Head into nearby Milton

Now I don’t want to play it off that Milton is close by, or that there is much to do here at all. But there is one restaurant that I absolutely fell in love with this past weekend. We’ve ordered pizza to-go from Boomerang plenty of times before, but I’ve never actually eaten inside before and wow- too cute. Disclaimer: if you’re not into artsy retro vibes, you probably won’t find Boomerang as endearing as I did. The food is great, don’t get me wrong (they even offer gluten free bacon mac n’ cheese), but it’s nothing fancy, so if you’re a high class kinda guy or gal, you may want to forego this one. My favorite part of the whole place however is the front of the restaurant, which is a gift shop of sorts filled with knick knacks and a candy bar with some of the best homemade fudge. Probably comparable with Dolly’s on the OC boardwalk. Sooo apparently my two favorite places also include fudge. Coincidence? I think not.

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Visit the Naval Aviation Museum

Whether you’re a history buff or know someone in the Navy/Marines, the museum is a cool place to spend an afternoon. We got lucky and had a great tour guide (aka my brother), but free, guided tours are also offered by the museum daily. Explore the different aircrafts or take part in a Blue Angels 4D Experience or flight simulator!

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Take a ride through the Holiday Inn’s lazy river

Probably shouldn’t recommend this one if you aren’t actually staying here, but from what we heard from all of the locals, admittance isn’t strictly enforced. However, by the end of our stay they had implemented a wristband policy I think for this reason. Rules are super lax in general in Pensacola, so grab your Bucket of Love or Pina Colada and jump in! Float around in pure bliss in the heated water, or jump into one of two hot tubs to unwind. Beware- the hot tubs are HOT, as evidenced by my claddagh ring that did not make it through my trip and has been permanently melted to my hand ever since spending the majority of my spring break in one.

Make friends with some random Wisco gals

Self-explanatory. Come into the hotel lobby for pool towels, leave with six new friends. Shout-out to all my loves who made our spring break such a crazy/fun/wild week!!

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Design your own dog at Dog House Deli

Yeah, you heard right. Hot dog lovers unite. What’s actually in a hot dog? No one really knows. What does it do to your body? I don’t really care. Two of my concoctions featured above. I believe the dog on the left was a BBQ dog with pulled pork, coleslaw and pickles, and to the right I went the more traditional route with ketchup, mustard, relish, you know, the works. Choose from a list of their specials or make a dog of your own!!

Eat and drink some more

Because it’s not like you have to put a bathing suit on right after or anything, right? Two more places to add to the list:

  1. Crabs We Got ‘Em: What a name. But KILLER chicken Caesar salads and, obviously, crab legs. Plus, although we missed it, Sunday brunch offers a bottomless mimosa option for only $6.99. Yes, please.

  2. Flounders: I’ve spent more than my fair share of time at Flounders. All I have to say is… seafood nachos and Diesel Fuels. Basically, think of the strongest Long Island Iced Tea you’ve ever had, and then double it. Warning you now, beware. What exactly is in such a potent drink? Try double shots of gin, rum, vodka and triple sec, with Coca Cola and sour mix. Or, ask for a turbo, and get an even more deadly mix made with Red Bull. The drink comes in a plastic Mason jar, and you can ask for a souvenir glass to-go, free of charge.

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Take a drive to the Santa Rose Shooting Center

Depending on where you are in Pensacola, this is about a 45 minute drive, but worth it if you’ve gotten a little bit too much sand in your pants and are looking for something different to do! Open to members and the public, more information about hours and pricing can be found here.

While I’ve been to Pensacola quite a few times, I’m sure I haven’t hit all the good spots. What’s your favorite place across the Bay Bridge? Or, what’s your favorite beach town? I’d love to visit them all 🙂

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