We rolled into Pensacola with growling stomachs, so our very first stop was food. We chose Philly’s Cheesesteaks & Hoagies – warm, cheesy, messy, and exactly what we needed after a long day of traveling. With full bellies, we were ready for bed for an early morning of exploring.
💡 Free maps, coupons, and a pressed penny machine
The next morning, we kicked things off at the Pensacola Welcome Center. It was the perfect place to grab maps, tips on things to do, and even a few coupons. But the real treasure? A pressed penny machine – because no trip of ours is complete without adding to the collection.
From there, we drove across the Bob Skies Bridge toll bridge to reach the Gulf Islands National Seashore. The water sparkled on both sides of us as we crossed, and honestly, the $1 toll (with Sun Pass) was a small price to pay, which made it even sweeter. *Without the Sun Pass, the toll was $3.50.
Inside the park, we explored Fort Pickens, a massive brick fortress completed in 1834. It once guarded Pensacola Bay and even imprisoned the famous Apache leader Geronimo in the late 1800s. The best part is that it’s completely open to wander at your own pace – we used the National Park Service app as our guide. The fort also offered staff guided tours every three hours. We ducked into tunnels, climbed up to the lookout points, and imagined what life was like there at that time – just fascinating…. until we noticed the ants. SO. MANY. ANTS. Needless to say, we watched our steps and moved very quickly after that.
📍 1400 Fort Pickens Rd, Pensacola Beach, FL 💰 $25 per vehicle for 7-day pass (free if you have an annual pass) 🌐 https://www.nps.gov/guis/planyourvisit/fort-pickens-area.htm Pro tip: Download the NPS app for a free self-guided tour 
There were spooky tunnels and dark walkways that made exploring the fort a little unnerving. 
In the photo, these tunnels look plenty lit. Take a few steps back and it looks like a dark abyss. These mine chambers were used during battle so soldiers within the fort could move kegs of gun powder from a powder magazine to a chamber. 
My husband is exploring through the fort 
We took this staircase up to the top of the fort, overlooking the land and ocean on each side. 
Isaac and I exploring the tunnels at the fort. 
This 15-inch Rodman is one of the largest smoothbore cannons ever developed, installed in 1868. This particular cannon was never fired in combat. 
All that exploring left us starving, so we were just driving to our next destination while looking for some food along the way. We stopped at a little place with flags and banners outside and skirt-skirted into the parking lot to find Pollo’s el Gordo. This place was an absolute GEM! The Enchiladas Verdes were perfection, the California Burrito could have doubled as a free weight (they put french fries in there, it takes burrito to an entirely new level), the torta was melt-in-your-mouth delicious, and yes, we finished with crispy, sugary churros. I would go back to Pensacola just for this!
🍴 Don’t miss the churros!
Now that we were happy and full, next on the list was the Naval Aviation Museum. The museum is on an Active Duty military base so you do have to show your Real ID with the gold star or if you are a DoD cardholder with base access already, then you’ve good to go. Getting in is easy – just stay in the left lane at the West Gate base entrance, show your driver’s license, right lane for DoD cardholders, and you’re in. The museum is massive, filled with planes of every kind, a portion of a ship was coming from the ground, plenty of history, and yes… another pressed penny to add to the collection!
Pensacola Lighthouse
Right across the street stands the Pensacola Lighthouse, which has guided sailors since 1859. Its 177 steps are worth the climb – the view from the top sweeps the bay and coastline. Down below, the gardens were in partial bloom, filling the air with the sweetest scents. We collected our Lighthouse Passport Stamp (with a $2 donation).
At this point, we were ready to wind down and fuel up for my husband’s race in the morning. We had dinner at Olive Garden to carb-up with the endless bread sticks, pasta and some salads.
It was the perfect end to a full first day in Pensacola – history, sunshine, great food, and just enough adventure to leave us excited for what’s next!
Park Passes & More Info.
- The National Park Service offers annual passes, so if you plan on visiting multiple parks in a short time or even within one year, it would be a great investment! They also offer a variety of discounts for students, seniors, military and disabled persons. National Park Passes can be purchased online or at the entrance of a National Park or historic site.
- Florida State Park Passes can be purchased online ahead of time or in-person at the entrance to a state park.
- If you’re visiting Florida and don’t have a Sun Pass, they can be inexpensively purchased at a CVS, Walgreens, Publix and so many more. To find the closest location to you to purchase a transponder in person, please visit the Sun Pass website. Or if you would like to purchase one ahead of time so there’s no stress while traveling, one can be sent out to you within a week of purchase according to this ordering page on the Sun Pass website.
- Pressed Penny Machine map – if the site hasn’t been updated in a while, I usually just call and confirm that they have a machine and that it’s working. After, I update that pressed penny page with the current date and that I collected however many pennies to show other collectors that it’s working.
While we didn’t venture any more after the race, we left Sunday morning, there were plenty of other beautiful things to check out if you’re staying in the area a little longer. I also recommend investing in the Florida State Annual Park Pass as well, since several of these remaining spots are withing the Florida State Park System and require an entry fee (waived with park pass).
- Big Lagoon State Park ($6 entrance fee)
- Perdido Key State Park ($3 entrance fee)
- Johnson Beach at Gulf Islands National Seashore ($15 per person entrance fee)
- Blackwater River State Park & State Forest ($4 entrance fee)
- Tarkiln Bayou Preserve State Park ($3 entrance fee)
- Fort Barrancas Area on Naval Air Station Pensacola (no entrance fee)
Get outside, soak up some sun, check out somewhere new!
This visit was so much fun and I can’t wait to see and read about your adventures! Please share photos if you use this itinerary!
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