See the Best of Tuscany in One Day With Walkabout Florence

Updated: October 1, 2026

I knew I wanted to see beyond Florence on this past trip to Tuscany, but I didn’t have much time. So I set out to find the perfect tour that fits my style. I loved that Walkabout Florence offered stops in multiple Tuscan towns, a vineyard with wine and lunch, and, most importantly, your own time to explore the towns separately from the group. That was key for me.

I love introductions to a city, but then I want to explore on my own. Of course, the time you get in each town isn’t nearly enough, but it gives you a glimpse of Tuscany and an idea of places you’d like to return to!

Tuscany in one day tour

The tour lasts 12 hours in the summer and 11 hours in the winter. You meet early in the a.m. and board a comfortable coach bus that will be driving you around Tuscany. A friendly guide joins the group and tells you more about the day as you head to your first stop. Our guide was Angela, and she was awesome! Here’s how the full day is broken down:

• Visit Siena
• Tuscan lunch at a Chianti vineyard (one of my husband’s fave wines!)
• Visit San Gimignano
• Visit Pisa

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First stop in Tuscany: Siena

Who knew Siena looked like this? This is definitely a town that we will be returning to! We had roughly 2 hours to explore Siena. The first hour was spent with a Siena local guiding us and sharing facts about this beautiful medieval city.

We learned about the world’s oldest bank, Europe’s oldest street, and explored the square where Europe’s most famous horse race, the Palio di Siena, is held. For the rest of the time, we were free to roam on our own, and I took full advantage with my camera in hand.

Second stop: Lunch at Fattoria Poggio Alloro

I have a feeling this is everyone’s favorite part! I know we absolutely loved our experience at the organic farm, Fattoria Poggio Alloro. If you’re ever in Tuscany, you can also book an overnight stay at the farm! Imagine how amazing that’d be?

When you first arrive, they give you a tour of their vineyards and introduce you to some of their sassy cows — loved them!

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They show you the olive trees used to produce their delicious olive oil. It was the best we’ve had, and we’ve tried plenty back home. From there, they lead you to a handful of communal tables set up for lunch.

Yes, I’m charging my phone lol!!

They give you an informal wine tasting before serving their yummy pasta, salad, cured meats, and some of the best cheeses I’ve ever tasted. We tried four different wines: 2 Chianti’s, 1 Vernaccia (my fave), and 1 Vin Santo dessert wine paired with biscotti. They placed full bottles of the first three wines per half table during lunch, so there was plenty to go around. We basically had 3 bottles to split between 2 other couples.

source: fattoriapoggioalloro.com

Another thing to note: the lunch is all organic, with ingredients grown on their own farm. The whole meal is delicious and worth the trip alone. Of course, they have a shop where you can buy their items or have them shipped to your home. It is incredibly difficult or expensive to find these specific wines elsewhere.

So, we bought 6 bottles of wine and a bottle of their delicious olive oil. The best part? We went on this two-week trip with one carry-on each, so you can imagine how fun it was trying to fit all that wine in our luggage. (We checked our bags on the flight home.)

Third stop: San Gimignano

For the life of me, I cannot pronounce the name of this place, but oh man, is it pretty. We were all full and happy after our Tuscan lunch, and San Gimignano was the most enchanting place to walk it off. We were free to explore the town on our own, yay!

Look at that stunning ivy!

Stuffed or not, we still made our way to the award-winning gelato shop named Gelateria Dondoli. We happily beat the crowd and enjoyed some of the best gelatos we’ve had in all of Italy.

After we got our fix, we simply did what we love best — walk the streets and take pictures. San Gimignano is a beautiful medieval city, with tons of photo opportunities. Yet another place we will be returning to.

Last stop: Pisa

To be honest, I could have done without Pisa, but that’s just the type of traveler I am. I’ve never seen the Leaning Tower, so that was cool to see, but I just wasn’t interested in the cliché photos. 

Either way, my husband and I were determined to find some charm in super touristy Pisa, and I think we did a good job. However, we won’t be returning to this Italian city.

Here’s everyone trying to keep the tower from falling ↓

I would have liked more time in Siena and San Gimignano to explore on our own, and I would have preferred to cut Pisa from the tour. But to each their own, right? 

After Pisa, we headed back to Florence (exhausted and content) and made it back by 8:45 p.m.

Final Thoughts on Walkabout Florence Tour

As you can see, you get a lot of bang for your buck with this Walkabout Florence tour. I do highly recommend checking them out. Especially if you’re nervous about driving in Italy on your own or want to explore more but have limited time.

They definitely provide a memorable experience. If you’re interested in this awesome Tuscany day trip, click here for the latest pricing and booking.

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Thank you to Walkabout Florence for sponsoring my tour through Tuscany. As always, these are my opinions. This blog contains affiliate links to booking sites and products I recommend. If you book or buy through my links, I may earn a commission at no extra cost to you. Your support helps keep this blog running—thank you for being a part of it!