Last Updated on March 5, 2024 by Marybeth
And you thought America’s oldest settlement was St. Augustine.
Pensacola has been drawing thoughtful attention lately, and for good reason. These days travelers are seeking fewer hot-spots lauded by mainstream trend-forecasters (which sounds to us like a horrible job.) Under-the-radar towns rich in history and brimming with bigger city amenities are coming to the fore.
More of us are looking for experiences where we feel our own sense of fresh discovery, not moving lockstep to the tune of oft-recommended popular vacation places. Let’s join in creating a new playbook, step off that beaten path, and point ourselves toward Pensacola.
Rounding up all of Pensacola’s recent awards – one of the best beaches in the country, top restaurants list of 2024, best farmer’s market – it might sound as though Pensacola is becoming one of those above-mentioned trendy vacation towns where you’ll find noisy crowds and bad traffic.
Not true.
Granted, there are numerous annual festivals and monthly events that draw like-minded compatriots: Pensacon, FooFoo Festival, Pub Crawls, Mardi Gras, Seafood Fest, and that best farmer’s market, Palafox Market. Somehow though, if you’ve decided to join a kindred tribe to celebrate, it will never feel like crowds of random tourists. And parking, which often feels like a barrier to having a great day, is easily found among downtown’s 19+ parking lots.
Whether you come to explore the famous main street – Palafox Street – or drive the short distance to that best beach, or sample the many foodie destination restaurants, we’ve discovered the best neighborhood for your headquarters. Here, in Historic East Hill, you’ll spend some of your best totally tranquil hours.
Historic East Hill itself offers plenty of spots to explore and enjoy. This gorgeous new vacation home, the East Hill House, below, is in a quiet, charming neighborhood where pride of place is evident. On a walk one morning I think I counted over 30 authentic bungalows. You may have noticed we use the term more broadly than the official architectural classification. Our last name is Bungalows, but the places we recommend for you aren’t always cottage- or bungalow-style at all. Some are restored historic hotels, some are restored roadside motels, some are breathtakingly brilliant new homes.
‘Bungalow’ is more of a feeling: room to spread out with family and friends if desired but also includes spaces that are small enough to feel intimate. That “this is all we need” vibe, with amenities geared to comfort and leisure. In cool, often peaceful, neighborhoods close to everything. (But not too close.)
STAY
The East Hill House is a fabulous, airy 4/2.5 home, accommodating 10 guests – bring your family, bring your travel team – central to so many options for meals out, carry-in, coffee, local brews, wine, shopping (Publix is 2 blocks away), local boat ramp (bring your boat), and an expansive, shady park with a playground, you could just contentedly stay in Historic East Hill for your entire visit.
The first thing you notice is the soft light streaming into the East Hill House. With its 10-foot ceilings and open living, dining and kitchen, the ambiance is pure delight – so many spots to lounge, gather for meals, sit at the generous kitchen island while someone (else) makes a meal. This home is a little bit glam! You might think modern farmhouse… No, more glamorous than that… But more cozy than glamorous implies… But this coastal-mixed-with-contemporary style doesn’t need categorizing. It is simply beautiful:
The East Hill House is family-owned by Superhosts, and is a short term rental, with a minimum stay of four nights. Longer midterm leases are available as well. You’ll want plenty of time to really see all there is to see in Pensacola, along with a not-to-miss visit to the beach. We were half joking when we said you could just stay in Historic East Hill for your entire visit. You may want to! It’s that tempting. But make sure you venture out. Then come home and relax:
Smart TV included.
One of our favorite things about the East Hill House was the plethora of outdoor ‘conversation set’ tables and chairs: the front porch, the upstairs front balcony, and the backyard covered porch (where you can sit and watch someone else grill your dinner.) And while conversation set implies sharing your space – which is great, and certainly fun! – one or more of us may have slipped out alone with a book and a beverage.
Besides plenty of serene spots to spend alone time, or chatting over meals, or catching up with our latest streaming series, a stand-out for us was the cohesive design. The colors are warm and beachy without being kitschy. Every design choice follows that aesthetic: the dinnerware, the cool polycarbonate wine glasses. Even the spoon rest looks artisan-made and chosen with intention. Not only well designed, but superbly well-stocked. Cook, bake, blend up some margaritas. Then make your plan to venture out and play!
PLAY
Historic East Hill Neighborhood
Before exploring further afield, make note of these worthwhile places to see around your neighborhood:
Alga Beer Co. is a 3-minute drive from the East Hill House, and has one of those origin stories that makes you either want to start your own brewery with your best friend, or at least visit Alga Beer Co. and sample a Tiki Sour Ale – “Extra Sauce,” or a Gold Medal Award-winning black lager – “Solitude.” Many more on tap, plus wine for people like me. Begun in Birmingham and Atlanta (AL, GA), an apartment balcony and a butane burner were involved. Talk about humble beginnings!
Brown Bagger Food Truck – “Phenomenal” and “The best burger I’ve ever had,” and so many more accolades we can’t list them all: just go. The hook for us was how much fun the chef and employees were having. With each order we heard a rip-roarious cheer go up – don’t you wish everyone felt that way about their jobs?
Old Sacred Heart Hospital
Within a short walk of the East Hill House is the historic Old Sacred Heart Hospital building, which has a fascinating history of its own (circa 1915, Florida’s first and oldest Catholic hospital, and later became a school) and is now home to multiple businesses, including just-opened The Burrow, a branch of Odd Colony Brewing.
We arrived a day too late to attend their soft opening, but as I walked around the next morning I was amazed at how pristine and clean the grounds were. Everything looked sparkling fresh and ready to begin another awesome day being a “whimisical little pub.” Dine cozily inside (“Burrow in”) or meet your friends for drinks, in or out. Plenty of room for everyone.
This stately building is also home to Ozone Pizza Pub – rumored to be haunted, which is a draw, but go for their delicious pizza – and A Mano Panino, which is inside Lamonte Gelato. Lunch, dinner, drinks, and dessert, all in the same building!
I’m not going to say we visit a place just because it’s lovely, but I’m not not saying it. Just around the corner from the East Hill House is East Hill Plaza, with Instagrammable The Daily Squeeze. After an over-supply of road trip food, a yummy cold-pressed Glow Up (carrot, orange, pineapple, ginger, turmeric) from The Daily Squeeze for breakfast was just the thing. An awesome way to start a busy day!
Take time to stop in Jitterbug Beverage Co.; the perfect combo of coffee, wine, and waffles, and Revolver Records, voted Best Record Store for 10 years in a row.
Palafox Street
Voted a Top 10 Greatest Street in America, and called “the New Orleans of Florida,” Palafox Street blends notable historic architecture (Spanish, British, and French – talk about a blend!) with chic boutiques, award-winning restaurants, and art galleries. Plan to spend hours here, wandering along the wide sidewalks, shopping, taking in the beauty and the dynamic downtown energy.
If you tend to plan your day around where your next meal will be enjoyed (like we do) you’ll have an array of excellent choices on Palafox Street and its surrounding neighborhood. Begin the day at 7 am at any number of cafes, bakeries, espresso bars, small-batch doughnuts + coffee.
Stroll the revitalized waterfront and pier…
Go shopping: as you roam north from the pier, drop in to Scout Boutique, Rusted Arrow Mercantile, Bluetique Pensacola, Sparkle, a Girl’s Boutique, Indigeaux Denim Bar & Boutique, and Innerlight Surf Shop, to name a few.
Learn the (Pala-)Foxtrot and the Cha-Cha at Plaza Ferdinand park, where the best farmer’s market happens on Saturdays.
Now that you’ve worked off that breakfast, the idea of lunch will be brewing*. You’ll find, on almost every block, intriguing-looking, or -sounding, restaurants (and possibly some choice-paralysis!)
And *yes, the word brewing is purposeful: we counted five breweries on, or just a block or two away from, Palafox Street. A wine bar, a wine tasting room, a whiskey bar, a patio bar, an Irish pub, and numerous cocktail bars. Many have become known for their winning mocktail recipes. It’s not always about drinking alcohol for us; especially if the day is still young and we have more to explore.
Some additional options for dining downtown:
For a comprehensive list of dining options in Pensacola – downtown dining, dining with a view, beach restaurants, happy hour, nightlife, sweet treats, and more, go to Visit Pensacola.
For you history and architecture buffs, delights are many. Beginning with that first settlement: six years before Pedro Menéndez de Avilés landed in St. Augustine, Spanish explorer Tristan de Luna established a colonial settlement at Pensacola Bay. St. Augustine claims to be the first because it is the oldest continuously occupied. (A Thrillist article, by travel and food writer Matt Kirouac, describes this whole thing as Pensacola “technically pre-dating attention hog St. Augustine.” They said it, not us! But it did make us laugh…)
Speaking of history, Historic Pensacola offers guided tours, self-guided tours, and virtual tours of the multiple museums and fort sites in downtown Pensacola. You can purchase a “One Ticket, Seven Days to Explore” pass and take your time visiting the Pensacola Museum of History, the Museum of Commerce, the Museum of Industry, the Children’s Museum, and more. Follow the America’s 1st Settlement Trail – a 3 mile marked path – with 20 stops and 70 points of interest, find the map here.
The Beach
Last but not least on your list – put it at the top, perhaps! Go early, go often. We didn’t (more on that in a minute) but the late afternoon was gorgeous:
Pensacola Beach is just a 15-minute drive from the East Hill House. With a boardwalk, a pier, countless waterfront restaurants, and watersports (nighttime glow paddling, parasailing, wave runners) this beach offers more than just stunning aqua waters and that powdery pure white (tiny pieces of quartz!) sand. You can park free of charge at Casino Beach Boardwalk, where you’ll see the iconic beach ball water tower. The Pensacola Beach Gulf Pier charges a small fee to walk out as an observer, and a little more if you’d like to fish (no license required.)
You may see a Blue Angels precision flight practice from the beach! Pensacola is the proud home base for the Blue Angels, at the Naval Air Station. Plan a visit to their National Naval Aviation Museum; admission is free!
For a more secluded beach day, head to the Gulf Islands National Seashore. Some of the entry points charge a fee. Fort Pickens is another peaceful beach destination. You’ll find historic structures, trails, picnic areas, a free tram, fishing pier (license required.) Find entry fee details on their website.
Just don’t leave your beach day until your last afternoon in Pensacola. After happily roaming the beach and marveling over the sand (ours on the Atlantic Coast is not quite that amazing) we hopped back in the car, excited to spend Happy Hour at our hosts’ top recommended waterfront restaurant, The Grand Marlin. I turned the key: nothing. Dead battery. Long wait for a tow truck, the drop-off at an auto parts store, installation of new battery, then home again long after dark – no happy hour at The Grand Marlin, no visit to the Sneaky Tiki, another host recommendation.
There is always a bright side: 1. We were ‘stuck’ at one of the most beautiful beaches we’ve ever seen. 2. We had leftovers from Joe Patti’s Seafood Market (exceptional, and famous!) for dinner when we finally got back to our gorgeous vacation home.
Book your stay at the East Hill House today!
- Lovely, quiet neighborhood
- Close to shopping (Publix!) and restaurants
- 10 guests, 4 bedrooms, 7 beds, 2.5 bathrooms
- Convenient for healthcare professionals: 10 minutes to 4 major hospitals
- Ideal for students’ families and professors: easy drive to 2 colleges
- Great location for Military and special ceremonies: 15 miles to NAS Pensacola
- 8 miles to the beach!
For a beach stay, check out Superhosts Pensacola Short Term Rentals’ Surf Shack on Pensacola Beach.
Pensacola Short Term Rentals on Instagram
We received a complimentary stay at the East Hill House, but as always, our opinions are our own.
