10 Day Trips From Florence, Italy: Tuscan Towns And Villages Worth The Trip
When I first moved to Florence, Italy, I had no idea just how many incredible places were right outside the city. Florence is essentially the heart of Tuscany, meaning within an hour or two you can reach medieval towns, vineyards, mountain villages, and even the coast.
After two years living in Florence and working as a tour guide for study abroad students, I’ve taken (and led) more day trips than I can count. Some are classics that everyone should experience once, while others are criminally underrated and rarely make it onto a tourist’s itinerary, which in my opinion makes them even better.
This guide covers the 10 best day trips from Florence, including how long each takes by car or train, what to do there, and which towns are truly worth the effort.
Note from the author: If this article gives you inspiration or helps in planning your trip please leave a comment! I love hearing from you and it helps me know what to write about more!
Why Pisa Didn’t Make the List
Let’s get this one out of the way: Pisa isn’t worth the trip.
The Leaning Tower is iconic and of course you could get that funny tourist photo, but once you’ve snapped it there’s not much else to see. The rest of the city feels a bit tired and overrun by tourist stalls. If you’re short on time, skip Pisa and use that day for a more authentic Tuscany experience.
1. Siena
Distance: 1 hr 30 min by car / 1 hr 45 min by train (with transfer)
Things to Do:
- Visit Piazza del Campo, the city’s shell-shaped square where the famous Palio di Siena horse race takes place. If you’ve never heard of this event (I hadn’t before moving to Italy) take a second to do some research on it. In my opinion it’s one of the coolest Tuscan traditions.
- Climb the Torre del Mangia for the best panoramic view of Siena.
- Step inside the stunning Siena Cathedral (Duomo) it’s one of the most detailed in all of Italy.
Why Go:
Siena feels like a time capsule. With its brick buildings, narrow alleys, and centuries of tradition, it’s one of the most aesthetic towns in Tuscany. Grab a spritz in Piazza del Campo, wander the historic streets, and soak in the medieval feel.
2. San Gimignano
Distance: 1 hr 10 min by car / 2 hrs by train + bus
Things to Do:
- Explore the UNESCO-listed Old Town and climb the Torre Grossa for countryside views.
- Try a scoop (or two) at Gelateria Dondoli, repeatedly voted the best gelato in the world.
- Stop by a local winery in the surrounding countryside. When I was guiding trips, we stopped at Fattorio Pagio Alloro, and I can’t recommend it enough. It’s an agritourismo that offers tastings, cooking classes, farm tours, and incredible views of rolling hills.
Why Go:
Known as the Town of Fine Towers, San Gimignano looks straight out of a fairytale. It’s small, walkable, and filled with artisan shops. The perfect mix of medieval and picturesque.
3. Lucca
Distance: 1 hr 20 min by car / 1 hr 30 min by train
Things to Do:
- Rent a bike and ride along Lucca’s Renaissance city walls.
- Grab lunch in the oval shaped Piazza dell’Anfiteatro, built on the site of an ancient Roman arena.
- Climb the Guinigi Tower, famous for the oak trees growing on its rooftop and panoramic views of the area.
Why Go:
Lucca is the calm, local antidote to busy Florence. You can explore at your own pace, stop for wine and aperitivo, and actually hear yourself think. It’s also one of the easiest towns to reach by train, no transfers needed.
4. Val d’Orcia Region (Pienza, Montepulciano & Bagno Vignoni)
Distance: 2 hrs by car (train not recommended)
Towns to Visit:
- Pienza – Famous for pecorino cheese, quaint alleys, and preserved Renaissance feel.
- Montepulciano – A wine lover’s dream with endless cellars and panoramic views.
- Bagno Vignoni – A tiny thermal village built around natural hot springs.
Why Go:
If you only have one day to see the real Tuscany, make it this one. The Val d’Orcia region is what you see on postcards; green hills, cypress lined roads, and vineyards that stretch for miles.
It’s the perfect Tuscany road trip loop: start early, stop in a few small towns, and end your day watching the sunset over the rolling hills.
Tip: This trip is best by car, but if you don’t want to drive, GetYourGuide offers several small-group tours that visit multiple towns in one day. No planning, no stress, just stunning views and good wine.
5. Arezzo
Distance: 1 hr by train / 1 hr by car
Things to Do:
- Explore Piazza Grande and admire Vasari’s Renaissance architecture.
- Visit the Basilica of San Francesco to see Piero della Francesca’s famous frescoes.
- Browse the Arezzo Antique Market (first weekend of every month).
Why Go:
Arezzo is one of Tuscany’s most underrated gems. It’s small enough to feel authentic but full of unique spots to explore. Once an important Etruscan center and Roman city, the city changed hands many times, making it the perfect destination for those hoping to dig into the history of Tuscany and its people.
6. Fiesole (mini trip)
Distance: 25 min by car / 30 min by bus from Florence
Things to Do:
- Explore the Roman amphitheater ruins and Archaeological Museum.
- Visit the Monastery of San Francesco for incredible Florence views.
- Enjoy a glass of wine or dinner at sunset overlooking the city below. My favorite spot is Ristorante la Reggia degli Etruschi for a nice meal. Or you can hit Lucky Hill Pub if that’s more your speed.
Why Go:
This one’s practically in Florence but feels like another world. It’s peaceful, scenic, and ideal for a half-day adventure when you don’t want to spend hours traveling. With just a short bus ride you’ll have views of the entire city and surrounding mountains.
7. Montepulciano
Distance: 1 hr 40 min by car / 2 hrs 20 min by train + bus
Things to Do:
- Go wine tasting at Contucci or De’ Ricci cellars right in town.
- Visit the Piazza Grande and tour the historic palazzos.
- Try the region’s signature Vino Nobile di Montepulciano paired with local cheese.
Why Go:
This town was already included in the Val d’Orcia region day trip, but you could really spend a full day exploring. Montepulciano is quintessential Tuscany; cobblestone streets, sweeping countryside views, and wine cellars tucked underground. It’s a bit of a drive, but every minute is worth it.
8. Volterra
Distance: 1 hr 30 min by car / 2 hrs 30 min by train + bus
Things to Do:
- Visit the Roman Theatre and Etruscan Gate.
- Shop handmade pieces from local alabaster artisans.
- Wander Piazza dei Priori, one of Italy’s oldest town squares.
Why Go:
You might recognize Volterra as an iconic Twilight Saga setting, but it’s so much more than that (and the actual filming location is in Montepulciano). It’s quieter than San Gimignano but just as stunning, with ancient history and scenic hilltop views.
9. Bologna
Distance: 40 min by high-speed train / 1 hr 20 min by car
Things to Do:
- Walk through Piazza Maggiore and the iconic Two Towers.
- Eat your way through Mercato delle Erbe or a local trattoria.
- Visit the Archiginnasio of Bologna, a 16th century university turned public library.
Why Go:
Known as Italy’s food capital, Bologna is where you’ll find the real tagliatelle al ragù (spaghetti bolognese) and countless restaurants serving up incredible Italian dishes. It’s also one of the easiest and fastest day trips from Florence, hop on a high-speed train and you’ll be there before your coffee gets cold.
Side note: Bologna is actually located in Emilia-Romagna, not Tuscany. That said, it’s still sure to deliver the vibes (and phenomenal food) you’re looking for.
10. Chianti Wine Region (Greve & Castellina)
Distance: 45 min by car / 1 hr 30 min by bus
Things to Do:
- Visit Castello di Verrazzano or Vignamaggio for wine tastings. Chianti is considered one of the best red wines in the world (I take my friends’ word on this as I’m not a red wine lover myself)
- Explore the charming town of Greve in Chianti and its artisan shops (check if you’ll be there for one of the annual wine festivals!)
- Drive the scenic SR222 Chiantigiana Road through the vineyards. (I personally followed this route)
Why Go:
If you picture Tuscany as vineyards and rustic farmhouses, you’re thinking of Chianti. It’s close enough to Florence for a relaxed afternoon and the perfect place to enjoy lunch with a view and a glass of local red wine.
Don’t Want to Drive? Try GetYourGuide
I’d be lying if I said there aren’t times my brain feels like mush while travelling. When this happens and I just don’t feel like figuring out a plan, I turn to GetYour Guide.
If you’d rather skip the stress of trains, transfers, and parking, GetYourGuide is hands down the easiest way to explore Tuscany and beyond. They offer guided day trips from Florence to almost every destination on this list; including Siena, San Gimignano, the Chianti wine region, and even the Val d’Orcia.
Why I love GetYourGuide:
- You don’t have to figure out transportation or timetables (especially helpful if you don’t speak Italian)
- Many tours include skip-the-line tickets, local guides, and wine tastings.
- You can cancel up to 24 hours in advance if plans change, super convenient.
If you want to see the best of Tuscany without the hassle of planning every detail, browse GetYourGuide’s Florence day trips and let someone else do the heavy lifting.
Getting Around Italy the Easy Way – Use Omio
If you’re exploring on your own, Omio is my go-to platform for booking transportation in Europe. You can compare train, bus, and flight options all in one place and buy tickets directly in English (no confusing Trenitalia website drama).
It’s perfect for planning day trips or longer getaways, especially if you want to explore cities like Rome, Venice, or Milan after your time in Florence.
Final Thoughts & Florence Travel Essentials
Florence is one of those places that only gets better the longer you stay, but getting outside the city is where you really experience Tuscany. From the vineyards of Chianti to the peaceful villages of the Val d’Orcia, every direction leads somewhere unforgettable.
Whether you rent a car, hop on a train, or join a GetYourGuide tour, these day trips from Florence are the perfect way to balance your Italy itinerary with adventure, good food, and countryside charm.
Before you go, make sure you’re packed with the right travel essentials and gear to make exploring easier (and more comfortable). You can shop all my go-to travel favorites, from luggage to Europe adapters, on my Amazon storefront.
