BUCKET LIST UPDATE No. 168: Take the historic downtown Pensacola walking tour

The William Dudley Chipley Monument.

I love walking tours, especially historical walking tours, so a couple of years ago, when I learned that there was a historic walking tour of downtown Pensacola, Fla., I immediately added it to my “bucket list.” 

On Saturday afternoon, armed with a printed copy of the walking tour that I found online, I made the short trip to downtown Pensacola, walked the route from start to finish, and officially scratched this item off my “bucket list.” In short, it was one of the coolest things I’ve done all year.

As you might have imagined, this tour takes place in Pensacola’s Downtown Historic District, and the centerpiece of this area is the Historic Pensacola Village, a small district that includes a number of historic buildings that’s staffed by re-enactors in period clothing. These folks were great and answered all of our questions about life in early Pensacola.

We parked behind the T.T. Wentworth Museum and paid a quick visit to the Tivoli House, which serves as a gift shop and ticket office for the Historic Pensacola Village. From there, we headed to the beginning of the tour at Plaza Ferdinand VII, which is often called the Ferdinand Plaza. The plaza contains a number of interesting items, including four old cannons, a really cool survey marker, a large fountain, a monument to William Dudley Chipley and an impressive monument to Andrew Jackson.

From there, we checked out the other sites along the tour, including the site of the Pensacola Opera House, the T.T. Wentworth Jr. Florida State Museum, the Julee Cottage, the Lear-Rocheblave House, the Pfeiffer House, the Dorothy Walton Cottage, the Moreno Cottage, Old Christ Church, Fountain Park, the Clara Barkley Dorr House, the Christ Church Parish School, the Charles Lavalle House and the Kate Coulson House.

For me, the highlight of the tour was Seville Square, which is a large park on the north end of the tour. Starting in 1559, this area was the site of several unsuccessful attempts to settle Pensacola by Spanish pioneers. It’s said that this was the earliest known attempt by Europeans to settle in what is now considered the North American continent. Later, Fort San Miguel was established on this site, and it later became a parade ground when a larger fort was built elsewhere along the waterfront.

All along the tour, we also encountered sites that are part of Pensacola’s Colonial Archaeological Trail, which present evidence of the early forts and buildings that once existed in this part of the city. These sites and displays give visitors somewhat of a hands-on idea of where early buildings were located, especially those used by early Spanish and English military occupants.

I’ve always enjoyed walking tours of this type because it’s a great way to learn about a city like Pensacola. I’ve lived a relatively short drive from Pensacola for most of my life, but I have to admit that I don’t know much about its history. Thank to this walking tour, I know a whole lot more than I did before taking the tour.

In the end, how many of you have ever taken the historic downtown Pensacola walking tour? What did you think about it? Do you know of any other walking tours like this one? Let us know in the comments section below.