Seeing Tuscany by Trail

An interview on the experience of seeing Tuscany, Italy through hiking!


The hike was a group hike, with two locals as a guide. It began and ended in Florence, visiting many small Tuscan villages in between! If you think you want to see the small towns of Italy, this interview spills all the details of what it is like to hike through them!

Thank you to Jodi, my aunt, who allowed me to interview her! If you are interested in gaining more information on how she arranged this experience, contact me!

Where did you go?

“My travels started in Florence, Italy where I stayed for 2.5 days on my own. From there I bused to the hill towns of Tuscany, those being Volterra, where we stayed for two nights hiking around the region there to olive groves and vineyards. Then we hiked to Colle Di Val D’Elsa and we stayed there a couple of nights and hiked around the region.  And then by bus we went to San Gimignano and took a bus tour there. Our final hill town was Siena. Then back to Florence from there to go home!”


What was your favorite city?

Volterra, it was very small, only 2,000 people, and it was just this quaint little village on top of a hill, and it was just neat.”

Did you like hiking instead of the typical modes of transportation?

“Yes because I got to see more of the country side and more of how the locals live and I got to see more than I would on a road. You feel more like a part of the country than just a typical tourist.

Did you get to meet any locals?

“While we were hiking on country roads and fields and people’s driveways. One particular day we were hiking when we came upon a small vineyard where the farmer was putting the grapes through the de-stemmer. He knew English really well and we got to talk to him for some time. It was very interesting to see a local and how he lived. Also, we visited a small family vineyard and had personal conversations with the owner and got to know about the struggles of owning a small vineyard in Italy.”

What was the price like compared to simply visiting a city on your own?

“It was more expensive because it was a tour. However, I think that I saw more than I would have if I were on my own. But it was worth it because everything is planned and we spent seven days with the two locals as our guides. That’s how we learned everything.”

How was it going in alone? Going into a group solo?

On being solo in Florence: “I was alone for 2.5 days. When you travel alone you are forced to talk to people because you are alone. At baggage claim I was standing beside an American and we ended up sharing a cab into Florence and had dinner two nights in a row. It was defiantly out of my comfort zone, but I wouldn’t trade it for anything. The second full day, I began to feel very isolated, but then I met up with my hiking group!”

Check out my post about Advice for Solo Travelers! If only Jodi could have known…

On being solo in a larger group of hikers: “When I met up with the group as the solo traveler, I didn’t feel out of place. The whole group was very welcoming and everyone was so nice. Our first dinner together, we went around and said why we were there. I said it was because I was tired of waiting so I did it alone. Everyone said they admired me for doing that. I always felt comfortable and I never felt alone.” Overall, Jodi would recommend doing the same thing to anyone looking into it, the solo part of the trip was never an obstacle to her enjoyment.

What was your favorite part about the experience?

“I really liked the hiking every day, and I liked seeing how people lived. I liked learning so much about the culture and their traditions of the Italians in the Tuscany region. I wouldn’t have learned it otherwise.”

What was your least favorite part about it?

“I don’t think I have one. There’s nothing that sticks out in my mind.”

Is there anything you wish you would have done?

She answered this question rather quickly, “Yes, I wished looking back on it that I would have extended my travel a few days and went to Rome while I was there.”

What was your favorite meal?


See the above image. “It was the best Italian meal I have had in my entire life. And then obviously their pizza.”

Do you have anything else you would like to add?

“Yes, a recommendation. One of the really good things I did for Florence was buying my museum passes to Uffizi Gallery and Michael Angelo’s David ahead of time! The lines were horrible and I got to walk up and right through the door. It was well worth it to buy the pass before you got there.”

Thank you, Jodi, for the wonderful interview!

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  1. Your aunt seems great 🙂 Cool post. I’ve been to some of these laces myself, Volterra is indeed beautiful. I agree hiking is a great way to explore a country.

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