Pensacola Beach
Pensacola Beach/Visit Pensacola

Pensacola, Florida has long been known as a resort destination for beach lovers across the United States. Here, (truly!) white sand blankets the beautiful coastline — reminiscent of the Caribbean, but just a short drive from most southern cities as well as the Midwest. What many people may not know, though, is that Pensacola is rich in history and has a burgeoning food scene. Here’s how to spend a perfect beach weekend.

What to Do
Naturally, the beach gets top billing in Pensacola, and the scene is a totally relaxed one. Public beaches are free and abundant; grab your umbrella, beach toys, and gear to spend a day on the sand.


If history’s your jam, head downtown and take a segway tour at Emerald Coast Tours — it’s incredibly fun to zoom around on these machines, not to mention educational. Tours run from one to three hours and cover the historical sites and neighborhoods of the city — all from the point of view of an expert local guide. Spoiler alert: You’ll learn cool facts like how Pensacola was discovered in 1559 by Tristan De Luna; this was roughly six years before the discovery of St. Augustine, making it the first European settlement in the U.S. A hurricane destroyed the entire settlement, and the settlers left before it could become an established city, which is why St. Augustine got the title of oldest city over Pensacola. Segway tours start at $43, and free walking tours are also offered.


While downtown, check out the incredible food scene by stopping at The Five Sisters Blues Cafe.

Downtown Pensacola
Downtown Pensacola/Visit Pensacola

Food & Drink
If you’re staying in the beach area, there are tons of options for great food and drink. Start your day at Native Cafe for the best breakfast on the beach. There will likely be a wait, but the biscuits and gravy will be worth it. Another popular hotspot is Peg Leg Pete’s, with terrific oysters and a lively atmosphere.

In the evenings, Casino Beach Bar & Grille is one of our favorite places to watch the sunset, sip a glass of wine, and scope out the locals playing volleyball and swinging in their hammocks. Flounder’s Chowder House features live music (think: ’80s and ’90s cover bands) and is known for a signature drink named the Diesel Fuel — an incredibly potent beverage that’s reminiscent of a Long Island Iced Tea that you should drink at your own risk. Hemingway’s Island Grill has stunning views and is named after the famous Florida resident. The restaurant’s décor pays homage to Ernest with rich woods and tiki cocktails.

And if there’s one thing you can’t miss in Pensacola? It’s sipping on a bushwacker. You can find this frozen, rum coffee drink at nearly any bar or restaurant in town — but most will tell you that the best is made by Sandshacker, home of the original.

Portofino Island Resort
Portofino Island Resort/Visit Pensacola

Where to Stay
There are loads of familiar hotel options along the main strip of Via De Luna Drive, including a Hilton, a Hampton Inn, and a Days Inn. But for something a little different, if you venture a bit further, you’ll reach Portofino Island Resort — a sprawling set of condos, situated on eight miles of the Gulf Island National Seashore. There are so many terrific aspects of this property, but we’ll start with the rooms, which are often under $200 per night. Each two- or three-bedroom condo is owner-rented and units have modern kitchens, dining areas, two-plus bathrooms, and large balconies, some of which overlook the water. Onsite, there are three restaurants, swimming pools, a pool bar, a full-service spa, and an all-access beach. This means that you can mosey down to the water and play on jet skis, hop on the stand-up paddle boards, kayak, and relax on the chairs — and the beach butler takes care of everything, for $25 per day.

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