See the Best of Tuscany in One Day With Walkabout Florence

Organic Tuscan lunch at Fattoria Poggio Alloro

I knew I wanted to see beyond Florence 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 don’t normally do tours). I loved that Walkabout Florence offered stops at multiple Tuscan towns, a vineyard with wine and lunch (most only offer wine), but most importantly that they gave you your own time to explore the towns separate from the group.

That was key for me. I love introductions to a city, but then I want to be able to explore on my own. Of course, the amount of time you get in each town isn’t nearly enough, but it helps give you a glimpse of Tuscany, and an idea of places you’d like to return to!

Streets of Siena, ItalyStreets of Siena, Italy

Tuscany in one day tour

The duration of the tour lasts 12 hours in the summer and 11 hours in the winter. You meet at 8:30 a.m. and board a comfortable coach bus that will be driving you around Tuscany. A friendly guide joins you and tells you more about the day as you make your way 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 Jorge’s fave wines!)
  • Visit San Gimignano
  • Visit Pisa

Click here for the latest prices and to book your amazing tour through Tuscany

First stop in Tuscany: Siena

Who knew Siena looked like this? This is definitely a town that Jorge and I 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.

Streets of Siena, Italy

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

Streets of Siena, ItalyStreets of Siena, ItalyStreets of Siena, ItalyStreets of Siena, Italy

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?

Click here to book this Tuscany tour

Organic Tuscan lunch at Fattoria Poggio Alloro

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

Organic Tuscan lunch at Fattoria Poggio Alloro

They show you their olive trees that help them make their delicious olive oil. It’s honestly the best olive oil we’ve ever tried, and we’ve tried many back home. They then guide you toward an area where they’ve set up a handful of communal-style tables for lunch.

Organic Tuscan lunch at Fattoria Poggio Alloroyes, I’m charging my phone lol!!

They give you an informal wine lesson before serving their yummy pasta, salad, cured meats, and some of the best cheeses I’ve ever tasted. We were able to try four different wines: 2 Chianti’s, 1 Vernaccia (my fave), and 1 Vin Santo dessert wine that’s 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.

Organic Tuscan lunch at Fattoria Poggio Allorosource:

Something else worth noting is that the lunch is all organic with ingredients grown on their very own farm. The whole meal is delicious and worth the trip alone. Of course, they have a shop where you can either purchase their items or get them shipped to your home. It is incredibly difficult or expensive to find these specific wines elsewhere.

Organic Tuscan lunch at Fattoria Poggio Alloro

So, we bought 6 bottles of wine haha, and also 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.

Organic Tuscan lunch at Fattoria Poggio Alloro

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!

Streets of San Gimignano

Look at that stunning ivy!

Streets of San GimignanoStreets of San Gimignano

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.

Streets of San Gimignano

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.

Streets of San Gimignano Streets of San GimignanoStreets of San Gimignano

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. The city is also having a big issue with girls pickpocketing people so it isn’t the safest city to wander.

Pisa, Italyeveryone trying to keep the tower from falling

Pisa, Italy

Either way, Jorge 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.

Pisa, ItalyPisa, ItalyPisa, Italy

I would have liked it better if we had more time in Siena and San Gimignano to explore on our own, and Pisa was cut out of the tour. But to each their own, right? 

Pisa, Italy

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

Pisa, Italy

Final Thoughts 

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 to drive in Italy on your own or you simply want to explore further 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.

San Gimignano

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Thank you to Walkabout Florence for sponsoring my tour through Tuscany. As always, all opinions are my own. This site contains affiliate links. I may receive a small commission for purchases made through these links at no extra cost to you. In turn, it helps to support this blog so I’ll be forever grateful.


  • Reply girlonthegoca June 15, 2017 at 8:01 am

    I love Florence! We were on a bus tour so I didn’t take advantage of a local walkabout, next time I will!

    • Reply This Darling World June 15, 2017 at 9:13 pm

      Just make sure you explore beyond Florence and visit some of the towns I mentioned above 🙂

  • Reply Taylor Fuller June 14, 2017 at 8:54 pm

    Take two: I’m pretty sure i had a friend who worked at walkabout when i lived in florence! i’m wondering if i should try them out when i go back!!

    • Reply This Darling World June 15, 2017 at 9:12 pm

      Really?! That’s so cool! They have all sorts of tours, one including fiats!

  • Reply Christie June 14, 2017 at 11:57 am

    This sounds perfect!! Especially the part about having your own time to explore too. I am the same way – I like tours to learn things I wouldn’t otherwise but then I GOTTA have time to explore on my own. Sounds like the perfect tour! I will check them out next time I am there.

    • Reply This Darling World June 14, 2017 at 12:35 pm

      Yeah that was really important to me, we all explore differently so I wanted to make sure I was able to do that. Def recommend it though, made it all a lot easier to see too. You know those Italian roads don’t play.

  • Reply In Between Pictures June 14, 2017 at 11:38 am

    I love Tuscany so much! It’s so pretty 😍 I wished I had stayed longer and join the tour. It looked like you had lots of fun. I’m totally with you on Pisa. I have never been but I find smaller Italian towns a lot more charming.

    • Reply this darling world June 14, 2017 at 11:45 am

      It’s such a gorgeous region with so many unique towns! I did have tons of fun on the tour, and highly recommend it. 🙂 And yeah, with Pisa you can just tell tourism has taken over the town — it sure still has its charm though!

  • Reply Dominick June 13, 2017 at 1:16 pm

    Love all your pictures. Now I really want to go to Italy. I’ve never been, even though it’s so close!
    Greetings from Germany!

    • Reply this darling world June 14, 2017 at 11:23 am

      Thank you, Dominick!! Italy has sooo much to offer, I highly recommend a visit. And yeah, you’re a train ride away! 🙂

  • Reply Adrian González June 11, 2017 at 1:34 am

    Great snapshot of what seems like a great trip! Definitely a good read for those of us who have never left their home country and want to ease into the experience! I don’t feel like I’ll be a touristy traveler so this is a nice balance.

    • Reply this darling world June 12, 2017 at 12:31 pm

      Thanks so much! It’s definitely a great way to sink your feet in to what Tuscany has to offer. 🙂

  • Reply Hanan June 10, 2017 at 9:08 am

    This is so dreamy Lily! You give me travel goals!!

    • Reply this darling world June 10, 2017 at 10:19 am

      Thank you, Hanan 🙂 It was such a fun, informative, and yummy tour!

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