Tuscany is famous for its rolling hills, quaint hilltop towns, cuisine, and wine. After my first visit to Florence back in 2017, I knew I wanted to go back one day and explore more of the countryside. I decided to take a day trip with the company Walks of Italy because they had my ideal itinerary planned out with transportation included. This was important to me because I wasn’t planning on renting a car during my stay. I’d done a day tour with them on my previous trip to Italy, and I really love how they take care of all the details for you. I also like how they give you free time to explore on your own. I like to wander off the beaten path and take pictures so flexibility is important to me as well. The tours are definitely on the pricey side, but it felt worth it to me since I was traveling solo on this trip and I knew I couldn’t fit so many activities into one day on my own.

Duration: 10 hours

Start time: 7:30 AM

Price: $186.00

Included: Tour leader, admission to Siena cathedral, lunch & wine tasting, transportation via private minibus, small group (18 or less)

https://www.walksofitaly.com/florence-tours/tuscany-day-trips-from-florence/

Siena

The first stop of the day was the medieval town of Siena. We toured the central square as a group, and then had some free time to explore the cathedral and wander the streets on our own. I really loved the interior of the cathedral, it had a huge wow factor. I would definitely like to go back to Siena one day and explore more.

Lunch and wine tasting in the Chianti Hills

After spending the morning in Siena we headed to lunch at a farm in the Chianti Hills. This area of Italy is absolutely stunning. It’s everything you dream about when you think of Tuscany. Olive farms, wineries, rolling hills, and postcard-worthy scenery. I didn’t really take any photos while we were having lunch, so I’ll just leave you with a picture of the olive farm we visited.

San Gimigano

After lunch, we headed toward the UNESCO World Heritage site of San Gimignano. I’ve had this town on my bucket list for a while now, so I was really excited to finally make my way there. We toured the town as a group, and then had free time to explore on our own. Per usual, I decided to climb the bell tower to get a bird’s eye view of the surrounding area. It was seriously one of the most amazing views I’ve ever seen. After sunset I grabbed some gelato and we made our way back to Florence.

My day trip through Tuscany was a day I’ll never forget. I had so much fun and met some really great people along the way. Now that I’ve gotten a little taste of what this region of Italy has to offer, I’d definitely like to come back one day and spend more time here. I highly recommend the tour company Walks of Italy as well. This post is not sponsored at all, I’ve just taken a few tours with them now and they plan everything out so well. It makes for such a stress-free day.