The Best Places to Eat and Drink in Pensacola, Florida

When I visited Pensacola, Florida, my husband (Eddie) and I found a host of delicious eateries that would satisfy even the most discerning palate. Pensacola, Florida (known as the Cultural Capitol of the Southeast) was established as the first European settlement in 1559. Since then, five flags have flown over the city, perhaps adding to its exceptional dishes and culinary options. You’re sure to enjoy these best places to eat and drink in Pensacola.

The Fish House

The Fish House is an upscale harbor-side restaurant with amazing views, a lively atmosphere (often with live music), and an extensive seafood menu. Eddie and I found a seat at the bar to watch a football game and started our meal with Caesar salads. The salads were delicious and have a light dressing that is just as flavorful as regular dressing.

For entrées, Eddie and I chose the Gulf Shrimp Plate and Fish of the Day, both blackened. I had smoked Gouda cheese grits and asparagus with mine and he chose French fries. The grits were incredibly tasty, had a great texture, and paired lovely with the blackened shrimp.

Five Sisters Blues Cafe

Five Sisters Blues Cafe is a bit off of the beaten path, but well worth a visit. Eddie and I arrived a few minutes before opening on Saturday morning and the line was already quite long. Sundays feature a jazz brunch, which we would have loved to try.

Five Sisters Blues Cafe has a fun vibe and great service. Although the Fried Chicken is the most popular dish, we chose differently. I had Red Beans Over Rice, which comes with a scoop of pulled pork or andouille sausage. The side item I chose was country green beans. I doused my red beans and rice in tons of hot sauce to make it just perfect. Eddie had the pulled pork bbq with onion rings and cheese grits. Our food was so tasty, we didn’t leave a bite.

If I lived in Pensacola, I would be a frequent customer at Five Sisters.

World of Beer

World of Beer is the spot in town to enjoy your choice of 500+ beers, a pub-style menu, and enjoy watching sporting events on the TVs. Eddie and I joined the locals of Pensacola to watch college football while enjoying our favorite craft beers on a great outdoor patio.

World of Beer has free Wifi, is pet-friendly, and has games, including Wednesday night bingo. The beer menus change often, but since you are in Florida, you might as well try something from a local such as Cigar City, Destin Brewing, Red Cypress, or Harris Meadery.

Jackson’s Steakhouse

Regarded as one of the top restaurants in Pensacola (maybe even Florida), Jackson’s Steakhouse takes your dining experience to a new level with a sophisticated setting and impressive service. Start your meal at this high-end steakhouse with the best Caesar salad you’ve ever had! The dressing is light, yet full-bodied, and weeks later I’m still craving it.

For a unique dinner option, I chose the Tournedos Trio, beef tenderloin medallions served three ways. Because they were so delicious, satisfying, and something I’m not used to seeing on a menu, I’ll share the description of each:

Americana Sautéed-mushrooms, garlic, thyme, red wine demi-glace, and Parisienne potatoes
Forestiere- mushrooms, pearl onions, lardons, petite pois crème, burgundy demi-glace, and Parisienne potatoes
Fried-Green Tomatoes- fried green tomato, jumbo lump crab, and Thibodaux andouille cream

My steak medallions were served with collard greens and three-cheese macaroni & cheese. Eddie had the Jumbo Lump Crab Cake. It is fair to say that both meals were exceptional, as was the service.

Another noteworthy mention is that anytime you get personalized butter dish for the bread basket, and artificial sweetener for your tea looking like a magazine photo shoot, you know you are in for a treat.

Fun fact: Jackson’s Steakhouse sits on the spot facing Plaza Ferdinand where General Andrew Jackson accepted the transfer of Florida to the US from Spain.

Casino Beach Bar & Grill

The friendly-vibe and laid-back atmosphere at Casino Beach Bar & Grill in Pensacola Beach will make you want to stay and sip a few more cocktails, or enjoy your favorite sporting events from the bar. For a more romantic option, enjoy dining al fresco on the deck. CBB’s menu has both Caribbean fare and Gulf Coast favorites.

Eddie and I sat at the bar and ordered Fish Tacos and the CBB Dinner (your choice of seafood). I went with the Blackened Shrimp which was finger-licking good! My shrimp came atop a mound of mashed potatoes with seasonal vegetables that were excellent. The tacos came with cabbage, pineapple pico (delicious!), Monterey jack cheese, avocado, and sriracha mayo. We both enjoyed the meal and happy hour drink prices.

The Ruby Slipper Cafe

Open for breakfast and lunch only, The Ruby Slipper (also found in New Orleans, Metairie, Mobile, Orange Beach, and Baton Rouge) is a breakfast lover’s dream spot. The buttermilk biscuits are unbelievable, taste wise and in looks. Perhaps that is why the every day wait is long to enjoy the delectable eats on the menu.

Eddie and I shared two entrees, which was probably a mistake seeing that one is truly big enough for two people. Ruby Slipper’s Trifecta (Eggs Benedict trio) may be the most genius creation I’ve seen to date. It features one each of Ruby Slipper’s famous Eggs Benedict:

Chicken St. Charles: Fried chicken and poached eggs over a buttermilk biscuit with a pork Tasso cream sauce
Shrimp Boogaloo: Think Shrimp Creole (pork Tasso), plus a fried-green tomatoes, poached eggs, and a buttermilk biscuit
Eggs Cochon: Apple-braised pork and poached eggs over a buttermilk biscuit with hollandaise.

I thought I had died and gone to heaven as I sunk my teeth into these heavenly Benedicts. I thought the Cochon would be my favorite, but the Shrimp Boogaloo won by a landslide.

Eddie and I also tried the Bam-Bam Biscuit which had bacon Eddie swears tasted like Christmas. They officially call it “pig-candy” bacon, but whatever it is, it is really sweet and yummy. The honking’ big buttermilk biscuit was stacked high with a fried-green tomato, pepper jack cheese, and a fried egg in addition to the bacon. We happily rolled ourselves out of the Ruby Slipper.

Cactus Cantina Mexican Grill

Cactus Cantina is a fun and incredibly popular Mexican joint in downtown Pensacola. The Tex-Mex menu offers a huge selection of flavors and sizes of margaritas, plus your favorite Mexican staples. Eddie and I had drinks and Chips & Queso in between our adventurous sightseeing. Our waitress suggested for us to add jalapeños to the queso, which made it more tasty. Cactus Cantina also has wine and beer, plus amazing happy-hour deals.

Tasty Pensacola

Eddie and I enjoyed visiting the beautiful and historic city of Pensacola, Florida, and especially eating our way around town. Whether you are looking for a national park (or seashore in this case), stunning beaches, family vacation destinations, foodie hotspots, or outdoor activities, Pensacola has them all. Pack your stretch pants; you’re going to need them with delicious eats like these.

To learn more about the cities of Pensacola, Pensacola Beach, and Perdido Key, visit this link.