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Fun Downtown Pensacola Things To Do: an Easy Florida Gulf Coast Trip

Fun Downtown Pensacola Things To Do: an Easy Florida Gulf Coast Trip

I love our hometown, but if I had to pick a new place to live, there are so many things to do in Pensacola, Florida and its islands that we would move there in a heartbeat. That’s not what this is about though. Having gotten to deeply explore the whole Pensacola area I have a great collection of unique things to do in each part of the city.

Pensacola is quite spread out and is very different from cities like Orlando or Naples, FL. I think it’s a mix of a few US cities: Savannah, GA; Mobile, AL and Portland, OR. It’s very unique, diverse and full of fun activities. Pensacola also is a city of festivals and community events, it’s very LGBTQ inclusive and I love it!

If you have any questions about planning a trip, fun things to do in the Pensacola area or just want to share your own recommendations, please leave a comment or send us a note. We’re always happy to share more!

Waterfront on Pensacola Bay

Check out more things to do in Pensacola: Pensacola Beach OR West Pensacola and Perdido Key

15 Fun Things to do in Downtown Pensacola

I think most people coming to Pensacola have a goal of making it to the beach, but before you get out to the beautiful barrier islands in the Gulf of Mexico, you have to make a stop in downtown Pensacola. Heck, you can easily spend a few days downtown dining your way around the city, visiting museums and historic sites, and enjoying all kinds of seasonal events and activities in Pensacola and then do the beaches.

Palafox Street

Wander along Palafox Street, the city’s main thoroughfare, lined with boutiques, art galleries, restaurants, and street life from morning until night. This is where you’ll find the Saturday farmers market which covers about five blocks. Also, street performers and artists line the street, both during market times and throughout the day, so it always sounds like a concert, even when it’s just a Tuesday afternoon.

Promenade on Palafox Street Historic Downtown Pensacola Florida 1

Pensacola Little Theater

There may not be a touring Broadway show here at the Pensacola Little Theater, but there are lots of other performances. Community plays, musical theater, local events, and film festivals all happen here. This non-profit theater is in a cool old building at the south end of downtown. It’s even got a bar in the atrium for grabbing a drink when you’re at the Pensacola Little Theater for a performance.

I got to spend several days hanging out in this space for the Stamped Film Festival, and got to know the people running the Little Theater. This is a great organization and they actively support youth and the LGBTQ community. Such a wonderful group!

Panel Discussion at Stamped Film Festival Pensacola Little Theater Florida 1

Historic Seville Square

Explore the historic heart of downtown Pensacola in Seville Square, known for its charming park, historic homes, and oak-lined streets. I really like wandering through this part of the neighborhood in the afternoon because it’s nice and shady. During the Pensacola Seafood Festival, a good portion of the Seville Square area fills up with booths and food vendors. Seville Square stretches to the marina, so you’ll probably end up here if you’re strolling the edge of downtown and the bay.

PS: as you walk around Seville Square and the surrounding streets, you’ll notice that it feels a little like New Orleans. Both Pensacola and Mobile AL were built up during the same period with some of the same people and influences developing the cities.

Wrought Iron Balconies in Historic District Pensacola Florida 2

Pensacola Historic Village 

Right next to Seville Square, the Pensacola Historic Village is a collection of historic homes, museums, and gardens that showcase the city’s history, and you’ll be surprised how many have weathered some intense hurricanes. The city likes to tout being older than St Augustine (our hometown), and it is in a way. Pensacola was a settlement before St Augustine was founded in 1565, but it was abandoned and later re-settled. But that means there are some wonderful old buildings and museums.

The Pensacola Historic Village is also where you’ll find the Pensacola Seafood Festival. The festival is loaded with food and music, and it takes over much of the Historic Village area. Hanging out here, whether you’re doing a historic tour or not, is one of the best things to do in Pensacola, especially if you want to see the quiet side of downtown.

Art Booths at Seafood Festival Pensacola Florida 1

Tivoli High House

Tour the Tivoli High House, a historic building that now houses the Pensacola Historical Society and has exhibits on local history, both recent and dating back to the origins of Pensacola as a settlement. Tivoli High House is next to… you guessed it… the Historic Village and Seville Square. This pocket of town really is cool and great to explore with kids and history buffs.

Saenger Theatre

Every part of the United States has their own collection of historic theaters, whether they’re Orpheums, Roxy Theaters or something else. Here in Pensacola, they have the Saenger Theater (sister venue to the Saenger in Mobile, AL). While you’re in Pensacola, see if you can catch a live performance or concert at the beautifully restored Saenger Theatre, an iconic downtown venue.

There are lots of great places to eat nearby, so you can make it a whole evening’s plan. Have dinner at Angelina’s (remarkable and delicious), see a show, and then go out for dancing and drinks, or just have a nice walk along Palafox Street.

Downtown Pensacola Art Walk

If your timing is right, you can’t miss the monthly Pensacola Gallery Night, where local artists and businesses showcase their talents and wares along Palafox Street. It’s like a farmers market, but in the evening and with mostly art and craftsman products for sale. I feel like there’s always music everywhere in Pensacola, so you’ll no doubt have live music during the art walk too.

Quayside Art Gallery 

I really like the Quayside Art Gallery. It’s across the street from the Pensacola Little Theater, so it’s easy to pop in and check out if you’re seeing a show or visiting the Historic Village area. Explore this cooperative art gallery featuring works by local artists, including paintings, sculptures, and more.

Tip: it’s perfectly fine to visit art galleries and treat them like museums even if you’re not in the market to buy art. It’s a great way to learn about the town, the local artists, and to just vibe-check what’s happening in Pensacola.

Quayside Art Gallery and Pensacola Little Theater Historic District Pensacola Florida 1

Downtown Pensacola Street Market

Saturdays in Pensacola mean that the boulevard area of Palafox Street gets turned into a market, both for farmers/beekeepers/mushroom foragers and artisans. It’s not quite as good as the Savannah Farmers Market at Forsyth Park, but it’s pretty great. Shop for unique crafts, jewelry, and locally made products at this open-air market, held on Saturdays from 9:00 am until 2:00 pm.

Saturday Market at Promenade on Palafox Street Historic Downtown Pensacola Florida 1

Hang out in Plaza Ferdinand VII (the central square)

Every city in the south has a cool square with benches, beautiful trees and a bit of history. Visit this historic square and park, where the transfer of Florida from Spain to the United States took place in 1821. For the arts walk afternoons, the square gets taken over by musicians and art booths, but the rest of the time it’s just like a square you’d find in Savannah or Brunswick on the Georgia Coast. There are a lot of similarities between Pensacola and Savannah.

PS: for all the time I spent chilling out here I apparently took zero photos, but it’s a lovely spot.

Pensacola Children’s Museum

We love visiting children’s museums, even as the kids get older. Until they’re teens and too cool for kid stuff, children’s museums can really be a hit and make an adult-focused trip feel more fun for a while (if kids are feeling road-trip-jaded). Bring the family to the Pensacola Children’s Museum, located within the T.T. Wentworth, Jr. Florida State Museum complex. It’s in the same general area of many of the other things to do in Pensacola’s historic district.

Historic Pensacola Trolley Tour

When people come visit us in St Augustine so many do the trolley tour, and I get it. Pensacola has a few too! Take a guided trolley tour to learn about the history and architecture of downtown Pensacola and take a break from walking on a hot day. There are a few trolley options in the historic district actually depending on the time of year. There is a free one provided by the city on select Wednesdays and Fridays, and then there’s the Beach Bum Trolley that operates with a ticketed ride.

Wrought Iron Balconies in Historic District Pensacola Florida 3

Arcadia Mill Archaeological Site

Yes, there are more things to do in Pensacola than just in the historic district near the bay. Discover the ruins of a 19th-century industrial complex just north of downtown, showcasing the area’s history and open to the public on Fridays and Saturdays. The Arcadia Mill Archaeological Site includes old mill works, historic buildings, interpretive displays and volunteers to tell you about the site. Donations are always appreciated as the site doesn’t get a ton of funding, but it’s pretty cool.

Pensacola MESS Hall

The Pensacola MESS Hall is not what you think. It’s not a bunch of cafeteria tables for soldiers, but a science experience, and it’s one of the best things to do in Pensacola with kids. The building is kind of unassuming, and the activities inside aren’t really what you expect. Visit this hands-on science museum for interactive exhibits and learning (you know me, always adding the learning thing into our trips). When you enter, you actually get to do science experiments and mess around with hands-on science concepts. It’s fun and way different than most other activities around downtown Pensacola.

Downtown Pensacola Food Truck Court

There is no shortage of restaurants in downtown Pensacola, but I’m always interested to see what sort of meals can be whipped up in food trucks. There is a pretty neat food truck court downtown, at the south end of Palafox Street, and it’s got everything from tacos to macarons. There’s even a bar in the inside/outside area of the food truck court. It’s the perfect place to eat with kids or if you’re got people with diverse tastes. It’s called the Garden at Palafox & Main and I love it! There’s plenty of shady seating and options for any sort of taste. The perfect example of what can be done to provide lots of food choices in a downtown area.

Food Truck Garden at Palafox and Main downtown Pensacola Florida 1

Where to Stay for a Pensacola Trip

I’ve stayed downtown Pensacola, stayed out at Pensacola Beach and stayed in Gulf Shores for different visits to the city. Depending on the what Pensacola things to do you’re planning, or if your whole goal is actually a beach trip, you’ll want to find a hotel that matches the vibe of your trip. I’ve enjoyed the beach vacation and the work trip to Pensacola, so here’s how I would recommend choosing where to stay.

If you’re planning on seeing a show or participating in a festival downtown, it’s VERY worthwhile to book a hotel in the historic district within a block or two of Palafox Street. The city is very walkable, so whether you’re close to the waterfront or you’re a bit north past Martine Luther King Jr Plaza, anything in this area is a good choice.

Because I’m all about the beach all the time, I like staying ON the beach. There are plenty of wonderful options for staying over at Pensacola Beach. From budget option to beach resorts, you’ll find it all. We do a lot of travel staying at IHG properties (Kimpton, Holiday Inn…) and here I really had a great stay at the Holiday Inn Resort Pensacola Beach. There’s just something about waking up in the morning and walking out onto the sand that I just love.

Clearly there are tons of things to do in Pensacola, Florida. It’s a fun city and I really love the vibe. It’s a wonderfully inclusive destination and is far ahead of the progressive curve of much of Florida. If you have any questions about visiting Pensacola, planning a trip to the Florida Gulf Coast or any other Florida travel, please leave a comment or send us a note. We’re always happy to help and share more!

I was surprised to discover so many fun things to do in downtown Pensacola. Being a beach destination, the historic downtown is actually full of museums, galleries and festivals. Here are 15 interesting things to do in downtown Pensacola that you can easily add to a beach vacation.