walking tour roundup: best fall walks

It’s no secret that Hannah and I are smitten with fall. Heavy heat just isn’t our thing–we’d rather take a grey day here and there with cooler temperatures. So as we feel now is one of the best times to explore the city, we thought we’d dig through the archives and share our favorite walks that will help you see more of Florence while enjoying the height of the season.

photo by Hannah

The Castle Hike

Ah, where it all began. This walk was the first to inspire us to write this blog. Take a tour of the hills of Settignano to Fiesole and delight in the fresh air, tall trees and stunning views. Mark your distance by the castles on the road, and keep your eyes peeled for the rare car or roaming cinghiale.


Via di San Leonardo

From the first to the last. Well, most recent. This is the walk Hannah and I kicked off our last trip to Florence stumbling upon. The winding road of Via di San Leonardo has more traffic than the Castle Hike, but it is equally as beautiful. On it you’ll explore life south of the city, ending your trip at one of our favorite spots, San Miniato al Monte.

Execution of Savonarola in Piazza della Signoria, Museo di San Marco, Florence, 1498

Execution of Savonarola in Piazza della Signoria, Museo di San Marco, Florence, 1498

Frightening Florence

Tis the season for a spook or two! This walk has its scares but is more steeped in the darker history of the city, with a few rumors thrown in for good measure. Want to up the creepy factor? Grab a flashlight and check out as many sites as you can under the cover of night.

Miu Miu by voodoox

Miu Miu by voodoox

Fashion as Art on Display

People in the city might just be starting to layer up as they head outside, but the fashion houses have been ahead of the season for awhile now. Take cues from their windows on how to dress on trend for fall. While you most likely can’t afford to restock your closet with what’s featured in their windows, this walk never fails to visually inspire.

Piazza Santissima Annunziata by Giuseppe Moscato

Piazza Santissima Annunziata by Giuseppe Moscato

Rainy Day Escapades

Ok, ok. We talk about how much we love fall, but we’re not going to ignore the elephant in the room. Fall in Florence means there are sure to be more than a couple rainy days ahead. But that’s ok! Hannah has you covered (literally) with this walk that takes you from loggia to loggia, so you can still enjoy the sites and the history without getting soaked to the bone. A good itinerary to have on hand for a weather-driven back-up plan.

Our friends acting too cool for the San Marco Pharmacy

Our friends acting too cool for the San Marco Pharmacy

San Marco Neighborhood

Finally, it’s time to show San Marco some love. Downtown always gets a ton of attention, and everyone is quick to head to the Oltrarno to check out the hip areas there. But Hannah and I have a soft spot for this neighborhood that we called home. Time to take in its charming gardens and piazze if you haven’t already.

There you have it–the walks that we would take to maximize the fall days in Florence. Do you have any favorites not on the list? Let us know!


  1. There’s just never a bad day to walk in Firenze!

    1. we certainly agree!

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