Florence is one of my favorite cities in Italy, but some of my favorite memories from that trip happened when we got in the car and explored beyond it. We wandered through Siena’s gorgeous cathedral, walked along Lucca’s walls, ate our way through Bologna, and stopped whenever a Tuscan town looked too charming to pass up.

You don’t need a car for every day trip from Florence, but it does make it easier to explore the countryside and combine smaller towns. Below are the trips I would choose, including which ones deserve a full day and which work best as a shorter stop.

Siena: Best Overall Day Trip from Florence

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Siena was one of our favorite stops in Tuscany, and if you can choose only one day trip from Florence, this would be mine. I would give it a full day. There is too much here to enjoy if you are rushing off to the next town.

The Duomo is the first place I would go. Its exterior is gorgeous, but what surprised me was that the inside is every bit as beautiful. Afterward, wander down to Piazza del Campo, the enormous shell-shaped square at the heart of Siena. My husband and kids climbed the Torre del Mangia while I took a break from walking and enjoyed the square from below.

Leave time for a good meal, too. We ate at Osteria Permalico, where I had ricotta gnocchi with a light pistachio cream sauce. It was one of the best things I ate on our entire Italy trip.

Lucca: Best for a Relaxed Day

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Lucca was one of our favorite towns in Tuscany. We drove there, parked outside the old city, and walked through one of the passageways in its enormous walls. Even that entrance felt like part of the experience—the cobblestones, sculptures, and lighting made it feel like we were walking into another time.

Once inside, you can walk along the top of the walls or rent bikes and ride around them. It’s a wonderful way to see the city without rushing from one attraction to the next. We also visited Guinigi Tower, which has trees growing at the top and views over Lucca.

Lucca is a good choice if you want a slower day than Siena. We combined it with Pisa by car, but I would happily spend more time just wandering Lucca.

Pisa: Best Quick Stop from Florence

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Pisa is busy, and yes, nearly everyone is there to see the Leaning Tower. We were too! Even after seeing it in countless pictures, it was fun to stand in front of it and watch the kids try to get their own tower photos. Now be warned that it is often hard to find a space to even take a picture. It is so packed, but be patient and your moment will come.

My husband and one of my sons climbed the tower, and I recommend making an advance reservation if you want to do the same. We paired Pisa with Lucca, which worked well for us: we got to see the tower, then spent more time wandering through Lucca.

San Gimignano: Best Tuscan Hill Town

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San Gimignano is the Tuscan hill town I would choose if you want medieval streets, towers, and an excuse to stop for gelato. The towers were built by wealthy families trying to show off their status, and they make the town recognizable before you even arrive.

We wandered through town and stopped at Gelateria Dondoli. It is thought to be the best gelato in Italy. While I can’t say it is better than others I have had, it is delicious. I loved the amarena gelato, and the lemon and hazelnut flavors were standouts too. If you want a view over the rooftops and countryside, you can climb Torre Grossa.

Bologna: Best Day Trip for Food

We went to Bologna for a simple reason: everyone kept telling us it had some of the best food in Italy. I’m glad we listened. We ate a delicious ragù, and that meal alone made Bologna worth the stop.

We also saw the historic University of Bologna, so the day was more than just lunch. If you’ve spent several days looking at Tuscan hill towns, Bologna gives you a different kind of outing: a lively city where you can wander between meals and take your time over the food you came for.

Chianti: Best Scenic Drive from Florence

Chianti is the day trip I would choose when you want to see the Tuscany you picture before you arrive: hills, vineyards, and little roads that make you want to pull over for another look. We drove through the countryside taking in the scenery and stopped at a castle because my husband can never resist a castle.

You don’t have to plan your day around wine tasting to enjoy Chianti. For us, the drive and the castle were reason enough to go. Give yourself time to stop when something catches your eye instead of trying to race through a list of villages.

Getting there from Florence: A car gives you the most freedom to explore the countryside and make spontaneous stops. You can reach individual towns, including Greve in Chianti, by bus, but that will be a different kind of day from a countryside drive.

Montepulciano: Best as Part of a Southern Tuscany Drive

Montepulciano was one of several charming towns we stopped in while driving through Tuscany. We got out, walked around, had gelato, and continued on our way. I enjoyed the stop, but I wouldn’t pretend we saw every corner of town.

From Florence, I would choose Montepulciano if you want a longer day exploring southern Tuscany by car, with time to stop at other towns along the way. It’s less suited to an extended outing than Siena or Lucca.

Getting there from Florence: Driving gives you the most flexibility for this trip. If you don’t have a car, I would look for a tour that includes Montepulciano rather than build a packed day around several public transport connections.

Certaldo Alto: Best Smaller Town to Wander

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Certaldo Alto from Florence: About 50–60 minutes by train to Certaldo, then walk or take the funicular up to the old town. Allow a few hours.

We found Certaldo Alto almost by accident and ended up staying inside its walled old town. It was one of my favorite surprises in Tuscany. The red-brick buildings, little streets, and hillside views made it feel wonderfully different from the better-known stops on our route. At times, it felt as though we had the place to ourselves.

Even if you don’t stay overnight as we did, Certaldo Alto is worth a visit if you like wandering through a town without a long list of things you’re supposed to see. Take your time and see where the streets lead.

 

Monteriggioni: A Short Stop on a Tuscan Driving Day

Monteriggioni from Florence: Roughly 50 minutes by car. Allow about an hour in town and pair it with another Tuscan stop.

Monteriggioni is a small walled town that we included while driving between Tuscan stops. Its walls and towers make it worth pulling over for, especially if you’re already heading toward Siena or San Gimignano.

I would treat Monteriggioni as a stop along the way rather than plan an entire day around it. That’s one of the pleasures of having a car in Tuscany: you can leave room for a town that catches your eye.

 

Cinque Terre: A Beautiful but Long Day Trip

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Cinque Terre from Florence: Allow roughly 2½ hours by train to La Spezia, then take a local train to the villages. This is a very long day trip; staying near the coast makes it easier.

Cinque Terre is beautiful, but I want to be honest about doing it as a day trip from Florence: it is a long day. We stayed overnight in La Spezia and still started early to make the most of our one day in the five villages.

We took the train from La Spezia to Monterosso al Mare and worked our way back through the villages. The coastal views were spectacular, but the crowds grew as the day went on. Corniglia was my favorite for its old-world feel and views from high above the sea.

If Florence is your only base, you can make the trip, but I would choose it only if seeing the coast matters more to you than having a relaxed day. If your itinerary allows it, staying closer to Cinque Terre gives you more time in the villages. Once you reach La Spezia, use the train to travel between them rather than trying to drive from village to village.

For more detail on the route we took, read my one-day Cinque Terre guide.

How to Choose Your Day Trip from Florence

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The best day trip depends on whether you want another city to explore, a small Tuscan town, or a day in the countryside.

If you don’t have a car: Start with Bologna, Lucca, Pisa, or Certaldo Alto. You can reach each by train and explore on foot. Siena is another good choice, especially by bus. San Gimignano is possible with a train-and-bus connection, but it takes more planning.

If you have a car: Use it for the places where the drive is part of the fun. Chianti is my pick for vineyard views and a castle stop. A car also makes it easier to visit San Gimignano or include shorter stops such as Monteriggioni and Montepulciano.

If you want to combine stops: We paired Pisa and Lucca, and I would do that again. You can also build a driving day around San Gimignano and Monteriggioni. I would keep Siena on its own if you want time for the Duomo, the square, and a leisurely meal.

If you only have one day: I would choose Siena for the fullest Tuscan city experience, Lucca for a slower day, or Chianti if what you really want is the countryside.

Which Day Trips Would I Save for Another Time?

If you have only one free day, don’t try to fit every famous Tuscan town into it. I would choose Siena on its own so you have time for the Duomo, Piazza del Campo, and a good meal.

Pisa and Lucca make a much better pair. Pisa was a shorter stop for us, while Lucca was somewhere we wanted to linger. Monteriggioni and Montepulciano also make more sense as stops on a longer drive than as separate round trips from Florence.

I loved Cinque Terre, but I would save it for a night near the coast if your itinerary allows. We started our one day there from La Spezia, and it was still a full day of exploring.

Day Trips from Florence FAQs

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What is the best day trip from Florence?

If I could choose only one, I would go to Siena. The Duomo is gorgeous inside and out, Piazza del Campo is a wonderful place to spend time, and there is enough to do to make a full day worthwhile.

What are the easiest day trips from Florence without a car?

Bologna, Pisa, Lucca, and Certaldo are good choices by train. For Siena, I would look at the direct bus as well as the train, since the train station is outside the historic center.

Can you visit Pisa and Lucca in one day?

Yes. That is what we did by car. We spent a shorter time around Pisa’s Leaning Tower and gave ourselves more time to explore Lucca. You can also plan the combination by train, but check the schedules before committing to tower tickets.

Do you need a car to visit Tuscan towns from Florence?

No, but a car gives you more freedom to visit the countryside and combine smaller towns. We loved being able to drive through Chianti and stop in places such as San Gimignano and Monteriggioni. If you would rather skip driving, choose a town with a train connection or book a tour for the hill towns.

Is Cinque Terre worth a day trip from Florence?

It is possible, but it makes for a long day. We stayed overnight in La Spezia before our one day in Cinque Terre and were glad we started closer to the villages. If you can stay nearby, I would; if Florence is your only base, start early and choose a few villages instead of trying to see everything.

Final Thoughts on Day Trips from Florence

Florence is one of my favorite cities in Italy, but I’m glad we made time to get out and explore. Siena’s Duomo, the walls of Lucca, and the little towns we found while driving through Tuscany are some of the memories I love most from that trip.

If you have time for just one day trip, I would choose Siena. If you want an easier day with a little of everything, pair Pisa and Lucca. And if it’s the rolling hills and vineyards you’ve been dreaming about, get in the car and spend a day exploring Chianti. You don’t need to see every town on this list—pick the trip that sounds most like your kind of Italy.

Still planning your time in the city? Read my guide to Florence with kids before you decide how many days to set aside for day trips.