View of Tuscan countryside

This is the third installment of my Italy vacation where I spent 11 days in Italy for only $150 using points and miles. We stayed in Florence for three nights¬†and used a full day to take a day trip to Tuscany. While Tuscany has so much to offer and I could’ve spent my whole vacation in this region alone, it was nice to get a feel for it with the limited time we had. Here’s how to see the best of Tuscany in one day!

Booking a Tour of Tuscany

You can get from Florence to other cities in Tuscany easily by train, but if you only have one day to explore, I highly recommend booking a tour. Having a private bus to bring you to each place really cuts down on the travel time, providing you with more opportunities to explore. We booked this tour on Viator. For just over $100, we got to go to Siena, San Gimignano, Pisa, and had a fantastic lunch at a vineyard. There were over 40 people on this tour, so you may prefer to spend more money on a private or small-group tour. We got plenty of free time at each of the stops, so being in a big group was less annoying than we thought it would be. Our tour guide was fantastic, so I do highly recommend this tour operator, Walkabout Florence.


Our tour group met at the Santa Maria Novella train station in Florence. We were escorted to our coach bus about a quarter-mile away. The tour guide provided us with some interesting facts on the hour-long drive to Siena.

Siena Cathedral
This was one of the most beautiful churches we saw on our entire trip.

In Siena, we had a city tour with a local tour guide. We then went to the beautiful Siena Cathedral as a group. Admission was included in the price of our tour. We were free to explore for the last hour of our time in Siena. I have to say, Siena was one of the best places we visited during our whole time in Italy. We were lucky to be visiting right before the Palio, a horse race dating back to the 1600s that is held every July 2nd and August 16th. The main square, Piazza del Campo, is filled with dirt to make a track around the perimeter. There are 17 districts, or contrade, in Siena, 10 of which are given a horse for the race through a lottery system. The race itself consists of three laps around the piazza and lasts less than two minutes.

While we didn’t get to see the actual race, the spirit of the Palio was in the air! We saw people from the different contrade dressed in traditional garb along with several ceremonial parades. I highly recommend Siena on its own, but it was even cooler to see with all the excitement leading up to the Palio.

Wine Tasting and Lunch

Next, we went to a winery and farm called Fattoria Poggio Alloro. We had a brief tour of the farm, olive grove, and wine cellar before indulging in a delicious four-course lunch and wine tasting. We had bruschetta, salad, pasta with beef ragu, a plate of meats and cheeses, and Cantuccini (almond biscuits). We sampled three wines during lunch and a fourth dessert wine with the biscuits. It was fun dipping the biscuits in the dessert wine, the way the locals do it!

I’m a big wino so we couldn’t leave without buying a case and shipping it home! We also so bought some of their delicious olive oil. It’s unlike anything you’ll find in the States. The views overlooking the vineyards with San Gimignano rising in the background made this the perfect place to get a taste of the Tuscan lifestyle.

View of San Gimignano
You can see the towers of San Gimignano on the righthand side.

San Gimignano

After lunch, we headed a few miles down the road to the medieval town of San Gimignano. This town is like a time warp back to the Middle Ages. As a bit of a medieval times nerd when I was little (thanks, Magic Treehouse books!), coming here was so cool. San Gimignano has a few points of interest. You can climb a tower or two, visit the church, and walk around the cobblestone streets and piazzas. There was not one, but two gelaterias claiming to be the best gelato in the world. Per our tour guide’s recommendation, Gelateria Dondoli is the one to go to. Our tour guide also said that she had people on previous tours that loved San Gimignano so much that they decided to stay and skip the rest of the tour!

San Gimignano


After San Gimignano, we drove an hour and a half to the last stop of the day, Pisa! The town of Pisa itself is not much to look at, but when in Tuscany, you’ve got to go see the Leaning Tower. When booking the tour, we had the option to pay more to climb the tower. We decided not to since we didn’t know how much time we would need to take pictures of ourselves pretending to kick the tower over. I was happy with our decision because our photoshoot took longer than you’d think!

Leaning Tower of Pisa
Another one off the bucket list!

The Leaning Tower of Pisa is part of the Piazza dei Miracoli along with the duomo, baptistery, and cemetery. The church is free to visit but you have to go to the ticket office and request a ticket. The other attractions cost money so we decided to admire them from afar. You really don’t need much time in Pisa, just enough to take some pictures outside of the tour and to pop into the church. After Pisa, the bus drove about an hour back to Florence.

Final Thoughts

While it was a long day, this was the best way to see as much as we did in one day. I highly recommend booking a day tour by bus if you want to fit multiple stops in Tuscany into a short amount of time. This tour was a good survey of the area and gave me a better idea of where I may want to stay in Tuscany in the future. Be sure to check out the next leg of our trip in Venice!

Do you have a favorite town or city in Tuscany?

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Best of Tuscany in One Day

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