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You are here: Home / How to Travel Alone / Touring the Tuscan Hills South of Florence

Touring the Tuscan Hills South of Florence

Janice Waugh

August 14, 2017 by Janice Waugh

A view of San Gimignano from the road. It's a hilltop town surrounded by 13th-century walls and is famous for its 14 medieval towers. Unlike the other towns in this post which are in the province of Florence, it is in the province of Sienna.

South of Florence, in the heart of Tuscany, are mountains that offer some of Italy's most beautiful landscapes.

Towering Cyprus trees, vineyards and olive groves fill the valleys below hilltop towns and mountain castles established in centuries past.

Driving to any of these towns involves winding roads at best and steep, hairpin turns at worst.

These are exciting places to drive to be sure.

I arrived there with Simon, my husband of just a few months now, towards the end of our roadtrip around the Adriatic. Our first stop was Castello Montegufoni, the castle where we would spend three nights and attend my brother's wedding.

Those of you who have been following the reports on this trip know that it was not solo. But how can I make such a trip and not share the experience and information I gathered? I can't. So, I've written lots. Here are other posts you may want to read.

  • Planning a Road Trip Around the Adriatic: Slovenia, Croatia & Italy – includes our plan and budget.
  • Travel Plan vs. Reality: European Road Trip – this includes what we actually spent including all the places we stayed from a hostel in Ljubljana, Slovenia to the castle in Tuscany.
  • Two Sides of Ljubljana: Historic and Alternative
  • Driving Tips for Europe: Written and Unwritten Rules of the Road
  • Travel Plans Change: Two Days in Dubrovnik
  • Bold Connection Makes for Magical Meeting: Umbria, Italy

The hills south of Florence are not just great for road trips but also cycling. There are buses that service the area but they are not frequent. You would only use these if you were not pressed for time. Rather than staying in busy Florence, staying in one of the small towns outside the city, like the Castello Montegufoni, is a good option.  The rate was CDN$175 per night. Not bad for a castle!

Now, here's the area in photos.

Castello Montedufoni was our big splurge of the trip. This is a view of the back garden. We saved the best for last. We started in a hostel, then a B&B, then our own apartment through airbnb and finally the castle. See what we spent on the whole trip here.
Castello Montegufoni. From upper left and clockwise: view of the tower from the courtyard, the wisteria trellis path, the courtyard from the other direction and the interior of the grotto that is near the pool.
On the left, a view from the castle and on the right a spectacular drawing room. That's my niece way in the back.
Not far from the castle was Montespertoli. Wandering the town on a very quiet Thursday morning we were attracted by Ceramiche Il Pozzo Montespertoli, a ceramics shop in the Piazza Machiavelli. We went in and were given a tour of the workshop in the back of the building as well. On a  daytrip to San Gimignano, we found this man’s ceramics in several shops at more than twice the price. You see the bowl on the right. I bought that and brought it home with a smaller one to match.
San Gimignano is the town famous for its 14 towers. The photos above are of the Collegiate Church of San Gimignano which is famous for its fresco cycles.
I cannot remember now the name of the town that had the food truck festival that we went to, but I don’t think that it matters that much as the festival is over. The point is, I suspect that we were the only tourists there. These small towns often have festivals that pull from the other small towns around but are really meant for locals. It was a wonderful experience. See the man in the top right? People were lined up many deep for his seafood in a cone.
And, of course, there are wineries. Stop off at any Direct Sale and buy some local wine and/or olive oil.
Last updated: 17th August, 2022

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