A Spicy Perspective

Tuscany, Italy: The Hill Towns

We had so many adventures in Tuscany that I’ve decided to split my Tuscany #TravelTuesday into two posts. Today we’ll share our adventures in the little hill towns and next week we’ll discuss vineyards, Sienna, and other aspects of Tuscany.

Exploring Tuscany, Italy: The Hill Towns on ASpicyPerspective.com #travel #italy #traveltuesday #tuscanyModern Art outside of Volterra by Mario Staccioli an Italian sculptor.

Ok, yes, you caught me. Sienna IS a Tuscan hill town. It’s kind of THE Tuscan hill town.

In fact it’s so much bigger than the rest, that we’re sharing our time in Sienna in next week’s post. This week it’s all about the itty bitty walled fortress towns that speckle the tuscan country side.

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We loved Florence. Yet after several days in the city we were ready to get out into some wide open spaces.

Traveling opens up a can of self discovery in many ways. We determined on this trip that we are not city people. We would much rather be out in the country, exploring nature and little villages. And that is exactly what Tuscany has to offer.

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Tuscany is dappled with dozens of tiny hill towns, each with its own flavor and intrigue.

They were built hundreds of years ago, with thick stone walls surrounding the exterior for protection from other near by towns.

Monteriggioni - Explore Tuscany, Italy: The Hill Towns on ASpicyPerspective.com #travel #italy #traveltuesday #tuscany

Over the years, through war and wear, many of the Tuscan hill towns have lost their walls and watch towers, and are now a reminder of a tougher time in history.

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Yet with the crumbling remains of fortified walls perched up on hill tops, and the preserved medieval buildings within, these little towns make the most marvelous places to stop on a road trip through the countryside.

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The beauty of roaming through this region, is that you don’t need a grand plan or agenda.

There are museums and cathedrals to see, just like in larger Italian cities. Yet the main attraction in each hill town, is the town itself… and the expansive views of Tuscany from high on the hill tops.

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Meandering along cobblestone streets, with high stone walls on either side, searching for the perfect sidewalk cafe to stop and have espresso, finding little artesian items only made in Tuscany to take home…

These are the things that make a trip to Tuscany memorable.

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In fact, we refrained from going in museums in the hill towns (and only went in a few cathedrals) focusing our time on driving the Tuscan country side, wine tasting, perusing shops, climbing towers, and of course eating.

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Of all the Tuscan hill towns, we decided to visit:  San Gimignano, Volterra, Monteriggioni, Montepulciano, Pienza, and Montalcino. (And Sienna.)

These were towns that were close enough in proximity that we could double-up in one day if we were ready to move on.

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If you are traveling through Tuscany and are short on time, you could easily visit:

Day 1:  Volterra and San Gimignano

Day 2: Monteriggioni and Sienna

Day 3: Monetpulciano, Pienza and Montalcino

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That’s not to say you couldn’t spend an entire day or more in each place (except for maybe Monteriggioni and Pienza.) Yet, if you are set on seeing as many hill towns as possible, this is how I would structure the road trip.

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What makes each town unique?

Well… that’s a hard thing to pinpoint in a short amount of time, but here’s what stood out to us…

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San Gimignano – is known for it’s astounding 14 towers still standing, of the original 72. The skyline is incredible.

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Volterra – is perched high on a steep slope, and is heavily fortified. It seemed a little less touristy than some of the hill towns and has the remains of a Roman theater.

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Montepulciano – The streets of Montepulciano are steep and winding, with little glimpses of the country side out side corridors. (You can also find some stellar wines here.)

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Montalcino – Another hill town focused on wine, with a fortress at the top that you can climb.

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Monteriggioni – is a tiny completely walled city that is fun for a quick stroll on the way to another hill town. You can walk on top of the wall, explore a few shops, and get gelato before moving on.

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Pienza – is another short-stop hill town. Be it small, it’s well-groomed with bold expansive views.

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A few tips on roaming the hill towns of Tuscany:

  • You can take a bus to all the hill towns, but this is a great time to rent a car. Change your navigation setting to the scenic route, roll down your windows and enjoy the drive through the countryside. Take the road less traveled… You won’t be sorry.
  • Opt to pay for the parking garages if available. Parking can be hard to find, and tourists are not allowed to drive into many walled hill towns.
  • If you plan to stop at only one or two of the hill towns, Montepulciano and Volterra were our personal favorites.
  • Climb! Many of the walled cities have watch towers still standing. The kids loved climbing up the rickety stair cases to look over the town. Along with getting a good bit of exercise, these towers provided some of the very best views.
  • Ask for restaurant suggestions. We ate at some pretty spectacular trattorias in the hill towns. We found our best bet was to ask a local shop keeper what was his/her favorite place to eat. We made sure to specify that we were not looking for fancy tourist spots.

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Now it’s your turn.

Do you have a favorite hill town in Tuscany that I didn’t mention?

If so, I want to hear all about it in the comments below.

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15 comments on “Tuscany, Italy: The Hill Towns”

  1. We went to Tuscany last summer and stayed at an amazing agriturismo outside of Pienza. Adored the small walled towns and realized we’re not big city people either.
    We’re planning our next trip but are afraid nothing will compare to Tuscany. Thinking Provence, France but the cities dont look as charming as Tuscanys. Also contemplating a Mediterranean cruise because our mother has mobility issues. But I’m afraid we won’t get a real feel of the area with only having a short day in the ports.

    Do you have any suggestions?

  2. AMAZING pictures!! Which lenses did you pack in your small bag? I’m traveling to Italy at the end of September and am still deciding what to pack. I don’t want to bring more than 2. thanks :)

  3. Such a beautiful area, someday I hope we can do the same.

  4. Never been to Italy. Wow it looks amazing! Great pictures. I think we’d have to visit at least a couple of those picture perfect towns lol my son would LOVE climbing those stairs and looking out as well :)

  5. Last summer we spent two weeks in Italy. We spent part of a day in San Gimignano and really enjoyed it. From there we drove on to Montepulciano, where we spent the night and part of the next day. One of our favorite towns as well.

    Thanks for sharing your experiences. Love Italy and look forward to going back.


  6. Wonderful photos and a great post. +1 on the bucket list.

  7. I am in awe! Every single photo looks like a painting. I’ve loved traveling along with you guys through your gorgeous photos. Thanks so much for sharing Sommer!

  8. Beautiful pictures! We spent several nights in Pienza and made it our home base when we visited other hill towns, so it has a soft spot in my heart.

  9. Beautiful photos, Tuscany is so picturesque!

  10. what a coincidence. we just got back from a trip to Tuscany. stayed in a renovated monastery near Gaole. food was great everywhere in Chianti.

    Summer’s photos are much better than ours.

    next time we are thinking of heading to Umbria.



  11. These are such gorgeous photos. I have been lots of places in Italy but haven’t really enjoyed the small town countryside. I would love too.

  12. We stayed at a winery between Pienza and Montepulciano for a week last month. I just received my case of wine yesterday from the fabulous La Dolce Vita in Montepulciano!

  13. Beautiful post! Amazing photos. I wonder if thise two kitties know how lucky tgey are!

  14. Sommer, these photos are so pretty. What a trip and what a beautiful place!! Thank you for sharing!

  15. What a beautiful recap of your trip! We loved Tuscany so much too. While the hubs and I enjoy seeing a city, we at our heart our country folks too :-) Love the outtakes of the kiddos.