The Perfect Florence to Tuscany Day Trip to Siena, Chianti and San Gimignano

Want to take a Florence to Tuscany day trip while you’re in Italy?

On my recent visit to Florence I knew I wanted to get out on a Florence to Tuscany day trip to see some of the other charming towns in the region. At first, I only knew for sure that I wanted to visit Sienna. 

Then, a friend of mine told me about San Gimignano and told me it was worth a visit as well. And, what’s a Tuscan day trip without a vineyard visit? So add Chianti into the mix as well. Read on for tips for planning your own Tuscany day trip from Florence, now that I’ve taken one myself!

Planning your trip? Use my go-to resources:

• Accommodations: booking.com
• Travel Insurance: SafetyWing
• Tours & Excursions: Viator
• Flights: Skyscanner
• City Pass: Go City

Your Florence to Tuscany Day Trip: Self Guided vs Group Tour 

When possible, I enjoy taking solo day trips via train or bus and exploring a new place at my own pace without crowds or timetables. So at first, I researched whether or not I could visit Siena and San Gimignano on my own. 

It turns out that visiting Siena from Florence by train isn’t too difficult. If that’s the only destination you care about getting to, then you could certainly book your own roundtrip train tickets and go spend the day there. 

Next, I looked into visiting San Gimignano on my own. There is no train station in San Gimignano, so the options for arriving there are either by bus, a train and bus combination, taxi, renting a car and driving yourself or booking a guided day tour. 

If you only want to visit San GImignano, you could probably do so easily enough via bus or the train and bus combo. 

However, I had limited time and was traveling with family who I wanted to also spend time with on this Florence trip. My ideal situation was to be able to visit multiple areas of Tuscany in one day. The best option for this was to book a guided tour. 

👉 Book your Florence to Tuscany Day Trip

Tuscany Day Trip from Florence Tour Overview

There are quite a few choices when it comes to booking a guided Tuscany day trip, so how do you choose the best one? I decided to book through a tour operator I’ve come to trust, after taking tours through them in various destinations. 

Here is an overview of the tour I went on to give you a sense of what to expect: 

Florence to Siena 

The day began reasonably early, around 8am, with tour guides and participants gathering in Florence’s central Piazza della Repubblica. After we met our tour guide and group for the day, we got into our comfy vans and began the route to Siena. 

But first, we stopped at Florence’s best viewpoint – Piazzale Michelangelo. On previous visits to Florence, I’d always come up here for sunset. Having the opportunity to stop there in the morning, when there are far fewer crowds, was a beautiful way to begin the day. 

Our first official stop was Siena, a charming town with a historic rivalry with Florence and camaraderie with Rome – as we learned from our guide. He also taught us about Siena’s 17 districts, or contradas, and explained the prominent role they play in Sienese life. 

In the main square, we learned about the Palio di Siena – an important horse race held twice a year each summer. 

Walking through Siena with an expert guide who carefully explained the stories behind what we were looking at left me with a better understanding of the city than if I had wandered through on my own. 

At the same time, I appreciated the balance of tour guide time and free time. After our guide led us to and taught us a bit about the cathedral, we were given time to explore Siena on our own. 

I chose to first buy a ticket to visit the cathedral’s interior, then went directly to find coffee as I hadn’t had any yet. I enjoyed a cappuccino and cream croissant sitting down right on the ground in Piazza del Campo, taking the lead from those around me. 

Once caffeinated, I made my way back to the cathedral and used my recently purchased ticket to go inside. It was nice to be able to spend leisurely time taking it all in, before reuniting with the group right outside. 

Chianti Wine Tour 

Back in the van, we were off to lunch and a wine tasting. Unlike wine-specific tours, we didn’t hop around to different wineries. Instead, we were able to familiarize ourselves with a lovely, 5th-generation gem in Monteriggioni. 

We got to tour their wine-making facility and fortuitously we were there during the only 10 days of a year when the air smells deliciously of wine due to harvest. 

What made our visit even more special was knowing that the 100% organic wine we’d be tasting was only available there, as the family does not work with any distributors and only produces wine using their own SanGiovese grapes.

After touring the small yet impressive facilities, we sat down at a beautifully set table to enjoy a multi-course meal with generous wine pairings. I learned the difference between Chianti and [the official] Chianti Classico, and we also tasted a couple varieties of balsamic vinegar. 

It was a leisurely and fun lunch with my fellow tour group members. The property we visited also has under 20 rooms they offer for guests to stay in and I’ve already decided I need to stay here on my next visit to Tuscany!

As we wrapped up lunch, we had the chance to purchase the exclusive wines we’d tasted and also to have them shipped back home (not the best option if home is Canada, we learned, due to high customs fees). 

Florence to San Gimignano

For our last stop of the day, we went to the medieval walled town of San Gimignano. The area was quite busy but beautiful and we had about an hour on our own to explore. 

I split my free time here between two activities – waiting in line at Gelateria Dondoli for ‘the world’s best gelato’ and taking in a sweeping Tuscan countryside scene from a viewpoint. 

It was glorious. 

The only thing I would’ve changed, or rather added, would’ve been an opportunity to see the town from a bit of a distance. San Gimignano is known for having an impressive skyline, with towers of different sizes shooting up toward the sky, and I would have loved to have seen it for myself. 

This the right Tuscany day trip for you if:

Wondering whether or not this is the best Florence to Tuscany day trip for you? Consider these factors: 

You want to experience Siena, San Gimignano and Chianti 

Of course, if you want to visit Siena, San Gimignano and a slice of Chianti for wine tasting then your wants align well with the itinerary of this tour. If, like me, you have limited time and want to experience all three in one day then that’s another reason to book this tour. 

And, if you want to visit these destinations without having to drive yourself or navigate public transportation then don’t hesitate to sign up for this experience. 

You prefer small-group tours and unique experiences 

If you’ve already done some research on Tuscany day trip options from Florence, you’ll know there are plenty to choose from. But one thing I loved about this tour in particular is the limit on a smaller group size. There were 14 of us, and this tour is capped at that number so you may have less but never more. 

This allowed us to get to know each other, as well as our tour guide. We didn’t have to follow a long line of people through crowds with an audio guide in one ear and an out-of-sight tour guide. In larger groups, it can be easy to feel lost in the crowd. 

Especially as a solo traveler, I appreciate the connections with others I get to establish more easily in smaller group settings like this one.

Another way to know this is the right tour for you is if you prefer more unique experiences. I love this tour company because they work to establish meaningful connections with local people wherever they host tours, which opens up opportunities for more immersive or special experiences. 

The winery we visited for our tasting with lunch is one such special place.

You appreciate a mix of guided tour and free time 

I started out this article by talking about self-guided vs group Tuscany day trips. What I appreciated about the guided tour I ultimately booked was the way it balanced a bit of both. 

If you’re someone who likes having the itinerary and logistics planned and executed by someone else, while also getting free time within it to wander on your own, then you’ll be happy with this tour option. 

FAQ: Taking a Florence to Tuscany Day Trip 

As you plan your Tuscany excursion, here are some final notes: 

Is Tuscany worth a day trip? 

Honestly, yes! While there’s so much of Tuscany you could easily spend more than a day exploring, even a day trip to Tuscany will expose you to many of the charms of the region.

Is Florence a good base to see Tuscany? 

As the capital of the Tuscany region and thanks to its network of trains and buses, yes, Florence is a great base for seeing Tuscany. 

What is the best day trip from Florence? 

This is the best day trip from Florence, in my opinion, for anyone wishing to visit Siena, Chianti and San Gimignano in an informed, fun and balanced way.

Final Thoughts on Your Florence to Tuscany Day Trip

The tour that you choose to go on can really make or break your experience of a destination. I hope this detailed overview based on my firsthand experience helps you confidently book your magical, Tuscany day trip! 

Being able to count on the fact that you’ll get a great guide, unique experiences and some time on your own throughout the day makes this a fantastic day trip option. Buon viaggio!

Disclaimer: Thank you to Take Walks for hosting me on this tour. All opinions, tips and recommendations are 100% my own, based on my first-hand experience.