Best Day Trips from Florence (and the Ones to Skip)

Florence might be one of Italy’s most visit-worthy cities in its own right, but it also happens to be one of the best bases in the country for exploring more of central Italy – especially if you don’t want to keep packing and unpacking.

Thanks to its excellent rail links and car hire access, you can dip in and out of wine regions, hill towns, and underrated cultural cities without having to move hotels. That said, not every popular day trip suggestion is actually a good idea. 

This isn’t a listicle-for-the-sake-of-it. 

I’ve included places I genuinely think are worth your time – and I’ll also explain why some of the most popular day trips might not be as enjoyable (or ethical) as they seem. 

A few entries are here because I know people are searching for them – but that doesn’t mean I recommend them.

If you’re just here for the quick answers, here’s what I’d tell a friend:

• For food lovers: Go to Bologna and do a food tour – it’s home to some of the best food I’ve ever eaten. 
• For a cultural city fix: Go to Siena – it’s Gothic, atmospheric, and utterly different to Florence.
• For something underrated: Head to Ferrara – it’s easy by train and full of quiet beauty.
• For a countryside feel: Take a wine tour or drive into Chianti – it’s the most accessible slice of Tuscan countryside from Florence.

In the guide to best day trips from Florence below, you’ll find a mix of easy train-accessible destinations, scenic drives worth renting a car for, and a few you might want to leave off your list entirely. 

I’ve also included practical details for each one – like how to get there, who it’s best suited for, and whether a tour is worth it – so you can make the right call for your own trip.

How do you choose the best day trip from Florence?

With so many options, choosing a day trip from Florence can feel a bit overwhelming – especially when every blog seems to list the same 15 towns. 

But not every place suits every traveller, and some destinations are better left for an overnight stay, or skipped altogether.

The right day trip for you depends on three things:

• What you want to experience – art, history, wine, views, food, or a slower pace
• How you want to get there – train, car, or small group tour
• How much energy you realistically have – day trips sound great in theory, but they can be tiring

Personally, if a journey involves more than one public transport leg (like a train and a local bus), I’m much less likely to take it. 

I either want one simple transfer, or I’ll rent a car or look for a small group tour that takes care of everything. That rule alone helps me narrow things down quickly – and it’s a helpful filter if you’re overwhelmed.

In the sections below, I’ll walk you through the most popular and worthwhile options, sorted by how best to reach them. You’ll find quick facts on getting there, plus my personal take on what makes each place interesting – or overrated.

Coming up first: the best day trips you can do directly by train.

---

Best Day Trips from Florence by Train

1 -Siena: Best for Art, Architecture, and Medieval Atmosphere

How to get from Florence to Siena

Best option: Bus or train

• By bus: ~1h15. Search schedules and book tickets here. Departs from Florence’s bus terminal near Santa Maria Novella and arrives at Piazza Gramsci, right in the historic centre – no uphill walk required.
• By train: ~1h30, direct from Firenze SMN. The station is located below the city – expect a 20-25 min uphill walk, or take the series of escalators and a local bus.
• Driving: ~1h15. Straightforward route and parking available near the centre.

---

Who should visit Siena on a day trip?

• Culture lovers who want a strong contrast to Florence
• Travellers drawn to medieval cities and dramatic architecture
• Visitors interested in Etruscan history and unique museums
• Solo travellers who want something easy but atmospheric

---

Why I recommend Siena

What really strikes me about Siena is the way its cathedral rises up above the city – perched so proudly at the highest point of the old town. It’s a proper goosebump moment, and you don’t often get that from a skyline.

Inside, the Duomo is genuinely one of the most stunning churches I’ve ever stepped inside. The striped marble, the frescoes, the flooring – it’s jaw-dropping. And to be honest, it makes Florence’s own cathedral feel surprisingly plain by comparison.

But what really surprised me the first time I visited was how much of a real city Siena still is. It’s not just a pretty hilltop town – it’s busy, lived-in, and distinctly different to Florence in its layout and energy, with its medieval streets and bustling local life. 

One of my favourite spots is the Ospedale di Santa Maria della Scala, right opposite the Duomo. 

Make sure to go all the way to the bottom – you’ll descend deep into the bedrock of Siena and walk through its layers of history, from Etruscan tombs to more recent centuries. There’s even a section where you can see actual human remains buried into the walls – it’s haunting, fascinating, and so unlike anything you’d find in Florence.

If you want a great city view, you’ve got two options: climb the Torre del Mangia (get there when it opens – you can’t book online), or head up to the panoramic terrace included in the Duomo museum ticket. Both are worth doing, but pick one and go early if you’re short on time.

If you’re planning a visit, I’ve also put together a detailed guide on what to do in Siena in a day – including my top tips for timings, tickets and views.

---

What to know before visiting Siena

• The bus is faster than the train and much more central – ideal if you’re not up for an uphill hike.
• Torre del Mangia tickets are only sold on-site only – get there first thing to secure yours.
• The Duomo museum terrace is not subject to timed entry (do expect queues of 30+ minutes later in the day though) and still gives you a brilliant city view.
• The Ospedale is unmissable if you’re interested in Etruscan history or immersive museum design.
• Siena is hilly – wear good shoes and plan for some steep walks.

---

Should you stay overnight in Siena instead?

If you’re planning to explore the Val d’Orcia or head deeper into southern Tuscany, Siena makes a fantastic overnight base. That said, it works really well as a day trip too – especially if you arrive early and focus your time around the Duomo and main sights.

---

Want to book a guided tour from Florence to Siena?

It’s surprisingly tricky to find a small-group tour that visits only Siena from Florence without going private – so if that’s your goal, it’s often best to make your own way there and join a tour locally. 

But if you’d rather have everything handled, this well-reviewed day trip includes Siena, San Gimignano and Monteriggioni – three of Tuscany’s most characterful spots – with lunch, wine, and transport all organised. Group size is capped at 25, so it’s not overwhelming.

2 – Bologna: Best for Food Lovers and a City Break Feel

How to get from Florence to Bologna

Best option: Train

• By train: ~40 mins on high-speed Trenitalia or Italo from Firenze SMN to Bologna Centrale. Trains are frequent, comfortable, and drop you centrally.
• Driving: ~1h30. You can drive, but there’s no advantage – the train is much easier.

---

Who should visit Bologna on a day trip?

• Food lovers keen to taste the best of Emilia-Romagna
• Curious travellers who’ve been to Florence before and want a contrast
• Visitors who want a full, satisfying day without cramming in major sights
• Anyone looking for an easy, direct train day trip

---

Why I recommend Bologna

Emilia-Romagna is Italy’s culinary powerhouse, and Bologna is its beating heart. 

You’ll find Parmigiano-Reggiano, traditional balsamic vinegar from Modena, mortadella, prosciutto di Parma, hand-folded tortellini, and gnocco fritto (the crisp, puffy deep-fried dough pockets often served with soft cheeses or cured meats – and sometimes a little scoop of lard, which is astonishingly good).

The tortellini in brodo was one also one of the best things I ate – so comforting and rich, even though I wouldn’t normally go for a brothy pasta dish. 

I joined the Walks of Italy / Devour morning food tour while staying in Bologna, and it was fantastic. But what really stood out was how many people on the tour had come from Florence on the train – and I thought it was such a smart idea. 

It’s an easy journey, the tour fits perfectly into a half-day window, and you still have time to wander and eat more afterwards.

Bologna’s aesthetic is shaped by its porticoes – the elegant covered walkways that line almost every street. There are over 60km of them across the city, and they’re now UNESCO-listed. 

Some are wide and grand, others are narrow and crooked, with faded ochre columns and vaulted ceilings – they make the city feel both lived-in and theatrical. They’re also perfect in both hot and rainy weather, giving Bologna its distinctive atmosphere of shelter and movement at once.

If you’re after more than just eating, don’t miss the Archiginnasio of Bologna – the city’s former university building, home to the Anatomical Theatre (an incredible carved wood lecture hall) and a stunning old library upstairs. 

Just make sure you book your ticket online ahead of time – we didn’t, and ended up waiting over an hour for the next slot.

I also really enjoyed the Pinacoteca Nazionale di Bologna, the city’s main art gallery. It’s often quiet, but the collection is exceptional, especially if you’re interested in the evolution of Renaissance art and early Bolognese masters. A calm, inspiring space that I’d absolutely return to.

---

What to know before visiting Bologna

• Trains from Florence are fast, frequent and reliable – book online for the best price
• Book the Archiginnasio in advance – the Anatomy Theatre is worth seeing, but queues build quickly
• The porticoes are beautiful and unique – and part of what gives Bologna its character
• Come hungry – this is one of the best food cities in Italy

---

Should you stay overnight in Bologna instead?

You could – I did, and it was lovely – but it also works brilliantly as a day trip. If your time in Florence is limited and you want to experience something completely different, Bologna is an easy and rewarding option.

---

Want to book a food tour in Bologna?

If you’re heading to Bologna for the day, this Tastes & Traditions tour with Walks / Devour is the one I did – and I absolutely loved it. You’ll need to make your own way there in time for the 10am start (the train from Florence is easy), but there’s plenty of time to fit it in. 

We visited loads of different local establishments, tasted everything from pasta to cured meats, cheeses, balsamic vinegar and wine, and learned so much about what makes Bolognese food so special. Genuinely one of the best food tours I’ve ever done.

3 – Ferrara: Best for Underrated Charm and Renaissance Elegance

How to get from Florence to Ferrara

Best option: Train

• By train: ~1h30 direct from Firenze SMN to Ferrara (no changes). The train is smooth, scenic and straightforward – I came into Florence from Ferrara myself recently and found it a total doddle.
• Driving: ~2 hours. Possible, but the train is more relaxing and central.

---

Who should visit Ferrara on a day trip?

• Anyone looking to escape the crowds and discover somewhere different
• History lovers curious about Italy’s lesser-known Renaissance cities
• Travellers craving an affordable, elegant, slower-paced alternative
• Anyone who’s already visited Bologna or Siena and wants a deeper cut
  

---

Why I recommend Ferrara

Ferrara was one of my favourite surprises in recent years. I spent three nights there and absolutely loved it – but even if you only have a day, it’s incredibly rewarding and perfectly manageable.

The city was a major Renaissance centre in its own right, ruled by the Este family, who poured money and vision into the arts. 

Their legacy is still everywhere – from the red-brick Castello Estense (a proper moat-and-turrets type castle right in the centre of town), to the atmospheric streets of the Jewish Quarter, and the elegant layout of the whole city.

There’s a calmness to Ferrara that I found incredibly appealing. It’s walkable, culturally rich, and feels very lived-in – not a place performing for tourists, but one that welcomes you in naturally. 

The Pinacoteca Nazionale is a must if you’re interested in art, and the city centre is perfect for strolling, with shaded lanes and arcades, independent shops and little surprises tucked around corners.

One of the best parts was the food. It’s fantastic – and notably more affordable than Florence or even Bologna. I ate so well in Ferrara for much less, and was surrounded by locals (plus the odd student or two) rather than tourists while doing so. 

---

What to know before visiting Ferrara

• The train is your best bet – easy, direct and drops you near the centre
• You won’t need to over-plan – Ferrara’s joy is in the wandering
• Make time for the Castello Estense and Pinacoteca – both are excellent
• The Jewish Quarter is a beautiful and moving area to explore

---

Should you stay overnight in Ferrara instead?

If you can, yes – I did and adored it. But if you’re based in Florence and looking for a calm, off-the-radar city experience that still offers rich history and great food, Ferrara makes for a wonderfully fulfilling and manageable day trip.

4 – Arezzo: Best for Renaissance Art Lovers and an Uncrowded City Feel

How to get from Florence to Arezzo

Best option: Train

• By train: ~1h15 direct from Firenze SMN to Arezzo (with regional trains running frequently throughout the day). Easy, affordable and central.
• Driving: ~1h15. Also very doable – especially if combining with countryside stops – but unnecessary for a focused city day trip.

---

Who should visit Arezzo on a day trip?

• Art and history lovers interested in the early Renaissance
• Those looking to escape the tourist trail without sacrificing character
• Travellers keen to explore a real Tuscan city, not just a hilltown
• Anyone curious about Vasari or interested in Medici heritage

---

Why I recommend Arezzo

Arezzo is one of those places that quietly gets under your skin. It’s not vying for your attention the way other Tuscan cities might – and yet, it has so much to offer if you’re paying attention.

I went primarily to see Piero della Francesca’s fresco cycle in the Basilica of San Francesco, and I genuinely found it moving. 

Painted between 1452 and 1466, the Legend of the True Cross is one of the most important fresco sequences of the early Renaissance. The way the narrative unfolds across the chapel walls – with that soft, mathematical precision Piero was known for – gives you this real sense of watching painting evolve. 

The church itself feels ancient, sombre, and intimate – so the moment you step inside, you feel the weight of history in the best possible way.

I was also drawn to Arezzo because of Giorgio Vasari, who was born here. I’ve always found Vasari fascinating – not just for his work as a painter and architect, but because he was the great storyteller of the Renaissance. 

His Lives of the Artists gave us much of what we know today about people like Michelangelo and da Vinci. But he wasn’t just chronicling the era – he was shaping it too. He designed the Uffizi and the Vasari Corridor in Florence, painted parts of the Palazzo Vecchio, and frescoed the interior of the Duomo’s dome.

In Arezzo, you can visit his own house, which he designed and painted himself in the mid-1500s. 

It’s not a grand palazzo – it’s a solid, comfortable townhouse – but it’s full of decorative flourishes and intimate artistic details that give you this rare glimpse into the domestic life of a working artist at the height of his career.

Beyond that, Arezzo offers a lovely pace of exploration. 

There’s a Medici fortress up at the top of town, a sweeping main piazza with a covered loggia, and a strong local feel that’s not overly dependent on tourism. 

You can spend the day dipping in and out of churches and other places of interest, but still feel like you’ve stumbled across something that many travellers overlook – which, to me, is the best kind of day trip.

---

What to know before visiting Arezzo

• The train is direct and efficient – no need to overthink this one
• Book tickets for the San Francesco frescoes in advance – numbers are limited
• Casa Vasari is a must for anyone interested in Renaissance culture
• The town centre is compact and walkable – you can see a lot without rushing
• Plenty of great lunch spots with a local crowd, not just tourists

---

Should you stay overnight in Arezzo instead?

You don’t have to – a day is more than enough to appreciate the highlights. But if you love slow travel and small cultural cities, Arezzo could make a lovely base for a night or two, especially as part of a wider loop through Tuscany.

6 – Lucca: Best for a Slow, Scenic Wander

How to get from Florence to Lucca

Best option: Train

• By train: ~1h20 from Firenze SMN to Lucca, direct and frequent. The station is just outside the city walls, a short, flat walk into the centre.
  Driving: ~1h10. Easy enough if part of a wider trip, but not necessary – the train is simpler.

---

Who should visit Lucca on a day trip?

• Travellers who prefer a slower pace and fewer crowds
• Those who want a relaxing day of walking, cycling, and browsing
• Visitors deciding between Lucca and Pisa and favouring charm over iconic sights
• Anyone seeking a low-stress, direct day trip from Florence

---

Why I recommend Lucca

Lucca is the kind of place that makes you slow down. It’s visually elegant and deeply atmospheric, with intact Renaissance-era walls that wrap the entire city in a 4km loop. You can walk or cycle the whole thing – and I really recommend doing so. The wide, tree-lined paths give you views over the rooftops, glimpses into courtyards, and the gentle rhythm of local life as you go. It’s peaceful, timeless, and has a lovely sense of ease.

Inside the walls, Lucca feels less like a tourist stop and more like a lived-in, working city. There are artisan shops, beautiful piazzas, and narrow medieval streets – plus two medieval towers you can climb for a view over it all.

• Torre Guinigi is the most famous, instantly recognisable by the oak trees growing on its rooftop. Yes – trees. It’s a short but steep climb (~230 steps), but the view is spectacular and totally worth it. Entry is €8.
• Torre delle Ore (the Clock Tower) is the tallest tower in Lucca and has a working clock mechanism. You’ll get a more open, panoramic view from the top. Slightly less busy than Guinigi, and great if you like cityscapes. Entry is €8.

Lucca’s wealth came from the silk trade during the late medieval and Renaissance periods, when it was one of Italy’s most prosperous republics. You can still feel that legacy in the architecture – grand merchant houses, arcaded streets, and churches commissioned by powerful families.

Lucca is a place to wander without pressure. It doesn’t demand a checklist – it just asks that you slow down and enjoy it.

---

What to know before visiting Lucca

• The city walls are walkable and cyclable – a full loop is ~4km
• You can climb both Torre Guinigi and Torre delle Ore for city views (€8 each, limited opening times)
• The train station is very close to the centre – no car required
• Lucca is great year-round and usually less crowded than Pisa

---

Should you stay overnight in Lucca instead?

You could – especially if you’re looking for a quiet base for a few nights. But it works beautifully as a day trip. Arrive before lunch and you’ll have time for a full city wall loop, a tower climb, and a slow afternoon exploring the streets and shops.

---

Want to explore Lucca with a guide?

If you’re making your way to Lucca independently, this small-group “Bikes & Bites” tour is a brilliant way to experience the town. 

You’ll cycle along the medieval walls, stop for local specialities at artisan food spots, and get a real sense of Lucca’s charm – all with a local guide and just your own group (private tour). It’s a lovely option for anyone keen to combine food, culture, and fresh air.

7 – Verona: Best for Romantic Atmosphere and a Scenic City Escape

How to get from Florence to Verona

Best option: Train

• By train: ~1h30-1h45 on a high-speed Trenitalia or Italo service from Firenze SMN to Verona Porta Nuova. Trains are frequent, and the journey is smooth – especially if you upgrade to business class for extra space. You’ll need to take a taxi or local bus into the city from the train station, FYI. 
• Driving: ~2h30. While doable, there’s no real advantage to driving – the train is more relaxing and drops you right in the city.

---

Who should visit Verona on a day trip?

• Travellers seeking a romantic, visually beautiful city with plenty of atmosphere
• Visitors who want a manageable, well-paced day in a walkable city
• Fans of Roman history, scenic riversides, and Renaissance architecture
• People looking for a good alternative to Venice or Rome as a long-distance day trip

---

Why I recommend Verona

I recently spent a month living in Verona – and it’s a place I’d return to in a heartbeat. 

Compared to places like Rome or Venice, which feel frantic on a day trip, Verona is that rare Italian city where you can see a lot and still feel like you’ve been somewhere, rather than just rushed through it.

It’s romantic and atmospheric in the best possible way: softly coloured buildings in rose and ochre tones, narrow stone streets, the curve of the Adige River wrapping around the historic centre. 

You’ve got Roman ruins, medieval churches, and elegant Renaissance architecture – all compact enough to explore on foot without getting overwhelmed.

The Verona Arena (a Roman amphitheatre that predates the Colosseum by about 50 years) is one of the city’s most famous sights – and still hosts opera performances during summer. 

There’s also Castelvecchio, a 14th-century red-brick fortress on the river, and the Lamberti Tower, which offers sweeping city views (and yes, you can take a lift if you don’t fancy the climb). Entry is just a few euro, and it’s a great way to get your bearings.

Food-wise, Verona has its own regional specialities that are quite different from Tuscany’s. One of my favourites was risotto all’Amarone, made with local Amarone wine – rich, dark, slightly bitter, and completely delicious. Pair it with a glass of the same and you’re set. 

The Veronese cuisine leans into robust, comforting flavours, and the wine scene is especially strong thanks to its location near Valpolicella.

As a bonus, the shopping in Verona is excellent – plenty of small boutiques and Italian high-street brands clustered around Via Mazzini and the main piazzas.

You’ll probably come across Juliet’s balcony – but I wouldn’t queue for it. The courtyard is chaotic, the walls are covered in old chewing gum (truly), and it’s more of a tick-box moment than anything meaningful. Still, worth a quick peek if you’re curious – just don’t waste too much time there.

If you only have one long day trip in you and want something a little bit special, Verona is a fantastic choice. It feels different from Florence in every way, and gives you a fresh sense of place that’s hard to beat.

---

What to know before visiting Verona

• Book your train tickets in advance – both Trenitalia and Italo run this route frequently
• You can climb the Torre dei Lamberti for sweeping views – there’s a lift and a small entry fee
• For something quieter and local, stroll over the Ponte Pietra to the east bank – it’s lovely over there
• Amarone wine and Veronese cuisine are a must – even just for lunch
• Verona’s Roman history is visible everywhere – the Arena, Porta Borsari, and even under shop floors!

Should you stay overnight in Verona instead?

You could – and I did, for a whole month – but it’s one of the few cities that also really works as a long-distance day trip. The centre is walkable, the journey is easy, and the pace of the city makes for a relaxing change from Florence.

Best Day Trips From Florence by Car or Guided Tour

8 – Chianti: Best for Scenic Drives and Tuscan Wine Tasting

How to get from Florence to Chianti

Best option: Self-drive

• Driving: ~1h to 1h30 depending on where you go – Chianti is a region, not a town, so distances vary. The roads are scenic and well-maintained, but winding in places.
• By public transport: Not recommended. While buses connect to a few larger towns like Greve, it’s difficult to access wineries or the countryside without a car.

---

Who should visit Chianti on a day trip?

• Wine lovers who want to taste Chianti Classico at the source
• Travellers craving Tuscan scenery – rolling hills, vineyards, and cypress-lined drives
• Visitors with access to a car who want an easy countryside escape
• Anyone wanting a slower-paced day that’s more about atmosphere than sightseeing

Why I recommend Chianti

Chianti is one of those rare regions that lives up to the postcard-perfect image – all vineyard-covered hills, stone farmhouses, and winding roads bordered by cypress trees. If you’re after a proper taste of the Tuscan countryside, this is the most accessible option from Florence.

I’ve visited several times and always found it rewarding – even on short visits. The roads are beautiful to drive (though you’ll want a car with decent horsepower if you’re tackling the steeper hill towns), and the scenery changes constantly as you move between valleys and ridgelines.

One trip that stands out was a romantic weekend staying at Vignamaggio, just outside Greve. It wasn’t a day trip – we stayed a few nights – but it reminded me how relaxed and immersive Chianti can be when you give yourself time. 

On shorter visits, though, you can absolutely get a feel for the region by choosing one or two villages to explore and booking a wine tasting in advance.

If you’re planning to drive, it’s a brilliant DIY option. But if you’d rather not worry about logistics (or who’s going to skip the wine), then a small group tour is a smart and stress-free alternative.

---

What to know before visiting Chianti

• The region isn’t one single destination – base yourself around Greve, Panzano, or Radda for an easy day trip
• Book your wine tastings in advance – many estates require reservations
• Avoid underpowered cars (like the Fiat Panda I once rented!) if you’re heading into hillier terrain
• Lamole is a gorgeous stop for lunch with a view – tucked high above the main Chianti towns, it offers spectacular vistas
• Wineries vary from high-end design experiences (like Antinori nel Chianti Classico) to small family-run estates – both are worth considering

---

Should you stay overnight in Chianti instead?

Yes – if you can spare the time, staying overnight lets you truly settle into the rhythm of the region. But if you only have a day, Chianti still delivers. Just choose one or two villages or estates and savour the slowness.

---

Want to book a wine tour of Chianti from Florence?

This small-group tour (capped at 14 people) includes tastings at three Chianti wineries, a traditional Tuscan lunch at a farmhouse, and scenic drives through the countryside – all with round-trip transport from Florence. It’s a relaxed, no-fuss way to experience the region without having to worry about driving.

9 – Val d’Orcia: Best for Iconic Tuscan Landscapes and Wine Lovers (if you’re up for the drive)

How to get from Florence to Val d’Orcia

Best option: Self-drive or private driver

• Driving: ~1h45 to Montepulciano or Pienza. Distances vary depending on which town you’re heading to. The drive is scenic but long – realistically pushing the limits of a day trip.
• By public transport: Not recommended. No direct trains, and reaching the main towns involves complex train-bus combinations.
• With a driver or small-group tour: Worth considering if your budget allows and you want a stress-free experience.

---

Who should visit Val d’Orcia on a day trip?

• Visitors who don’t mind a long drive for spectacular countryside
• Wine lovers interested in Brunello di Montalcino or Vino Nobile di Montepulciano
• Slow travel enthusiasts who want to potter through peaceful towns and scenic roads
• Those with a bigger budget who can book a driver or tour for the day

---

Why I recommend Val d’Orcia (with caveats)

Let me be honest: Val d’Orcia is magical, but it really pushes the boundaries of what I’d consider a day trip from Florence. The drive alone is around 1h45 each way – and that’s before you factor in any stops, winding roads, or time to explore.

That said, it’s one of the most beautiful areas in all of Tuscany. If you’ve ever seen those cinematic shots of rolling green hills, lone cypress trees lining dirt roads, and stone farmhouses silhouetted against the skyline – this is where they were filmed.

On one trip, I looped down through Pienza, San Quirico d’Orcia, Bagno Vignoni, while transiting from Montalcino to Montepulciano – and it was breathtaking. The road climbs and dips through open countryside and golden light. 

Bagno Vignoni in particular left a mark: it’s just a tiny hamlet centred around a large pool of thermal water, and it was the perfect place to stop for a slow, scenic lunch.

Of all the towns, Montalcino is my favourite – it feels quieter and more upmarket than Montepulciano, with a clear focus on its famous Brunello wines. Montepulciano is still worth seeing (and should absolutely appear alongside the others), but Montalcino felt like the real prize: small, atmospheric, and less crowded.

If you’re already familiar with Tuscany and don’t mind the long drive, you’ll be rewarded here. But if you’re short on time or unsure about navigating country roads, I’d honestly suggest staying overnight or skipping it in favour of something closer.

---

What to know before visiting Val d’Orcia

• It’s a long round-trip from Florence – ~3.5 hours of driving total
• Roads are good, but they’re winding and rural – best tackled in daylight
• You’ll need to choose a handful of towns – don’t try to do everything
• Montalcino, Pienza, San Quirico, and Bagno Vignoni make a lovely loop
• Book winery tastings ahead of time, especially in Montalcino and Montepulciano
• Parking is relatively easy in most towns, though expect to walk uphill in a few

---

Should you stay overnight in Val d’Orcia instead?

Yes – without hesitation. This region really shines when you stay a night or two and experience the pace of it properly. You’ll also be able to enjoy long winery lunches, scenic drives, and quiet evenings without rushing. If you can swing it, it’s the kind of place worth lingering in.

---

Want to book a Val d’Orcia tour from Florence?

If you’re not planning to drive, this small-group tour (capped at 8 people) is a thoughtful, well-paced way to see the Val d’Orcia’s most iconic towns in a single day. 

It includes guided visits, wine tastings, and time in Montalcino, Pienza and Montepulciano – without the chaos of a big group. It’s not cheap, but for this region, smaller is better.

If your budget doesn’t stretch to a small-group experience, this larger tour is one of the more popular alternatives. Just be aware it’s a full bus tour (up to 45 people), and while convenient, it’s not the most mindful way to explore a place as special – and fragile – as this.

10 – San Gimignano: Best for Towering Views and a Sense of Time Travel (but only if done right)

How to get from Florence to San Gimignano

Best option: Self-drive or small-group tour

• Driving: ~1h15. Straightforward route with good roads. There’s a paid car park outside the town walls.
• By public transport: Not ideal. You’ll need to take a train to Poggibonsi, then a public bus to San Gimignano. It’s doable, but it’s a multi-step journey that makes it less suited to a smooth day trip.

---

Who should visit San Gimignano on a day trip?

• Architecture lovers drawn to medieval towers and golden-stone streets
• Wine drinkers curious about Vernaccia, Tuscany’s most famous white
• Travellers with a car or on a well-paced small-group tour
• Anyone willing to explore slowly, spend money locally, and avoid the worst crowds

---

Why I recommend San Gimignano (with reservations)

San Gimignano is undeniably striking. Its medieval skyline of jutting towers and ancient stone rises like a mirage from the Tuscan hills. When you’re there, especially in the quiet moments, it genuinely feels like you’ve stepped into a postcard or walked onto a film set.

But I have complicated feelings about it.

I’ve stayed in San Gimignano, I’ve passed through it, and I’ve wandered its streets in that uncanny twilight lull between the tour buses leaving and dinner service starting – and that’s when the magic happens. Without the crowds, the place breathes.

By contrast, arriving into town during the day is shocking. 

On my last visit, I remember walking down its main spine and being stunned by the crush of day-trippers pouring in through the gates. It felt more like a queue through a theme park than a town with soul. 

And that’s what worries me – I’ve seen firsthand how overtourism is slowly sucking the life out of this place.

That said, it’s still worth seeing – but only if you visit independently or on a small-group tour, and if you take the time to experience it properly. 

Wander beyond the central streets. Look up. Notice the striped awnings over residential doors. Spend money in actual shops. Have a proper meal. Engage. Don’t just take photos and leave.

A quiet but powerful highlight for me were the fresco cycles inside the Collegiata di San Gimignano. They’re genuinely some of the most beautiful and clearly told that I’ve seen in any church – vibrant, expressive, and laid out in a way that walks you through the story. 

I used the audio guide, which talks you through both cycles in sequence, and it made the whole experience feel intimate and absorbing. 

What struck me most was that despite the crowds outside, barely anyone else seemed to go in to see them – I couldn’t believe it. It was calm, moving, and such a contrast to the bustle beyond the church doors.

Another standout moment was walking the town walls at golden hour, catching glimpses of the countryside, and suddenly being struck by the fact that people still live here – in homes wedged into this living museum. And then sipping Vernaccia di San Gimignano, the local white wine, in a quiet restaurant as the light softened. 

It can be special – but only if you tread thoughtfully. To be honest, I think it’s better kept as somewhere to overnight. 

---

What to know before visiting San Gimignano

• There’s no direct train from Florence – getting there by public transport requires a train-bus combo
• Driving is the most flexible option, especially if you want to explore the surrounding wine country
• The town gets overwhelmingly busy with tour groups – aim to arrive early or late
• Climbing the Torre Grossa, the tallest tower, offers brilliant views
• Don’t skip the Civic Museum (inside the tower) – or just wandering the quieter backstreets
• Vernaccia wine is the local speciality – it’s crisp, minerally and quite different from Tuscany’s famous reds

---

Should you stay overnight in San Gimignano instead?

Yes – or at least nearby. Staying in or just outside the town gives you access to its quieter side, and you’ll get the full impact of its beauty after hours. Accommodation isn’t as limited as people think, and some of the restaurants in San Gimignano are genuinely excellent.

---

Want to book a small-group tour to San Gimignano from Florence?

If you’re not driving and want to visit San Gimignano in the most respectful, enjoyable way possible, this small-group tour (max 8 people) is a brilliant alternative to the typical 50-person bus tours I’d strongly advise against. 

You’ll have a quieter, more considered visit – and it includes Volterra too, which is a perfect pairing.

11 – Volterra: Best for Avoiding the Crowds and Soaking Up Etruscan History

How to get from Florence to Volterra

Best option: Drive

• By car: ~1h30 from Florence, with gorgeous views en route. You’ll climb steeply into the hills as you approach Volterra – the drive up alone is worth it.
• By public transport: Not ideal. You’ll need to take a train to Pontedera or Empoli, then a bus to Volterra. Doable, but slow and with awkward timings. Driving is far easier.

---

Who should visit Volterra on a day trip?

• Travellers looking for a less-touristy alternative to San Gimignano
• Anyone interested in Etruscan, Roman, and medieval layers of history
• Those who prefer quiet streets and a slower pace of exploration
• Visitors with a car who want something more off the beaten track

---

Why I recommend Volterra

I visited Volterra while en route between San Gimignano and Siena, and I remember being immediately struck by how peaceful it felt compared to its more famous neighbour. 

I was there in May – shoulder season – and even then, it was delightfully calm. I’ve heard it does get busier in summer, but it still tends to fly under the radar compared to San Gimignano.

We parked near the Roman amphitheatre, which made for an atmospheric entrance into town – it’s right at the base of the city, and you climb up from there. 

Volterra is compact, beautifully preserved, and full of texture and charm. The medieval architecture is striking but not overwhelming, and the scale of the town makes it ideal for a relaxed half-day visit.

One of my favourite parts was walking down the artisan-filled Via Porta all’Arco – we passed a traditional ironworker and a few little art galleries – which led us to the Etruscan gate, a hulking piece of history that’s been standing since the 4th century BC. 

Although I didn’t make it to the Etruscan Museum (I just wasn’t feeling up to it that day), it’s high on my list for next time – Volterra is one of the best places in Tuscany to explore Etruscan history in depth. 

And if you don’t fancy museums, it’s still a brilliant place to just potter – the town’s full of winding streets, lovely boutiques, excellent views, and quiet corners.

Volterra rewards visitors who slow down – who aren’t rushing to tick boxes, but are happy to stroll, to pause, to absorb. It’s not about grand must-sees. It’s about texture, story, and silence.

---

What to know before visiting Volterra

• The Etruscan Museum is closed one day per week – check opening hours ahead of time
• You can see the Roman amphitheatre, Etruscan gate, cathedral and baptistery all in a relaxed couple of hours
• It’s built on a high ridge – expect beautiful views and hilly terrain
• There’s limited public transport – driving is by far the easiest option
  

---

Should you stay overnight in Volterra instead?

If you’re driving through the region slowly, Volterra makes a peaceful and characterful overnight stop – especially if you’re visiting San Gimignano and want a contrast. But for most people, it’s absolutely doable and rewarding as a half-day or full-day trip from Florence (if you’re driving).

---

Want to book a day tour to Volterra from Florence?

This small-group experience (limited to 8 guests) lets you explore two of Tuscany’s most atmospheric hill towns without the overwhelm of a coach tour. 

You’ll visit San Gimignano and Volterra in one day – a great combination if you’re short on time and want to experience both with a little breathing room.

12 – Vinci & San Miniato: Best for Leonardo Lovers and Truffle Tastings

How to get from Florence to Vinci & San Miniato

Best option: Drive

• By car: ~1hr 15mins round-trip loop. Start in Vinci (~1hr), then drive 30 mins to San Miniato. From there, it’s ~45 mins back to Florence.
• By public transport: Train to Empoli, then local buses – possible, but awkward. This is a day best done with a car.

---

Who should do this day trip from Florence?

• Leonardo da Vinci fans keen to see his birthplace
• Curious travellers looking for a peaceful countryside loop
• Foodies visiting in autumn (truffle season!)
• Anyone craving a more under-the-radar Tuscan experience

---

Why I recommend Vinci & San Miniato

I visited Vinci as part of a wider Tuscany road trip, and what really struck me was how peaceful and off the beaten path it felt. 

The town itself is quiet and compact, with a strong sense of place – and it’s absolutely worth stopping into the Museo Leonardiano while you’re there. The museum gives a proper look at Leonardo’s inventions and engineering work, which is often overshadowed by his paintings. 

After visiting the Leonardo Museum in town – which has a decent collection of models and sketches – we drove up to his birthplace, the Casa Natale di Leonardo. You can also walk up (about 20-30 minutes uphill), which would be lovely if you had the time.

The house itself is simple and rustic, with a short film that gives context to Leonardo’s early life and environment. There’s something very grounding about seeing where he began – in this quiet hilltop spot, surrounded by olive trees and silence. We had the place almost to ourselves.

Adding San Miniato makes the trip more varied – and it’s especially appealing if you’re a food lover. 

The town is famous for its white truffles, and during truffle season (typically late autumn), you’ll find shops and restaurants offering seasonal dishes and special menus. San Miniato produces around 25-30% of Tuscany’s total white truffle harvest, and it hosts one of the most important truffle fairs in Italy. 

Even outside of truffle season, it’s a lovely place to wander – the old town is elegant and compact, with panoramic views and a mellow pace. It doesn’t take long to explore, but it feels like a true discovery. 

---

What to know before visiting Vinci & San Miniato

• Casa Natale di Leonardo is ~3km from Vinci town – you can drive or walk
• Entry to the museum + house is ticketed (combo tickets available)
• San Miniato sits between Florence and Pisa – if you only have time for lunch or a stroll, head to the upper town for views and restaurants
• White truffle season is October-December, with festivals in mid-November
• This is a quiet, non-touristy itinerary – ideal if you’re craving a break from busy sites

---

Should you stay overnight instead?

No – unless you’re already on a rural retreat. These towns are small, and best enjoyed on a slow day out with Florence as your base.

---

Want to book a tour to Vinci and San Miniato?

While this experience doesn’t include Leonardo da Vinci’s birthplace, it’s a brilliant alternative if you’re more drawn to food-focused activities. 

You’ll explore the forests near San Miniato with a licensed truffle hunter and dog, learn how truffles are foraged, and enjoy a multi-course lunch featuring your finds – with local wine, of course. 

A unique way to experience this part of Tuscany through its earthy, gourmet soul.

Popular Day Trips from Florence I Don’t Recommend

While plenty of people do these as day trips from Florence, I personally wouldn’t advise it. Here’s why – along with the travel logistics for each, so you can make your own call if you’re still tempted.

These aren’t bad places. In fact, I love all three. But I believe they’re best experienced on their own terms, not squeezed into a rushed itinerary that risks reducing their magic to a box-tick.

---

1 – Venice

How to get from Florence to Venice

• By train: ~2h on high-speed Trenitalia or Italo. Trains are frequent and arrive at Venezia Santa Lucia, which drops you on the Grand Canal.
• Driving: ~3h. Not recommended – Venice is car-free, and parking is expensive and far from the centre.

---

Why I don’t recommend it as a day trip

Venice is one of the most over-touristed cities in Europe – and day-trippers are a huge part of the problem. The city even introduced a day visitor tax to help cope with the pressure.

Personally, I don’t believe in contributing to that strain for the sake of a whirlwind visit. Venice deserves more time. It’s a city best experienced slowly – wandering its quieter corners and getting lost in the backstreets, gorging on cichetti and sipping on spriztes in between museum and gallery visits. 

Of course it’s possible to go for the day, and the trains make it logistically easy. 

But rushing through Venice to see St Mark’s Basilica and the Doge’s Palace alongside 20,000 others won’t show you the best of the city – it’ll just leave you hot, tired, and frustrated. 

If Venice is on your list, make it its own trip. It’s worth it.

---

2 – Rome

How to get from Florence to Rome

• By train: ~1h30 on high-speed Trenitalia or Italo to Roma Termini. Trains are fast, frequent, and drop you right in the city centre.
• Driving: ~3h. Not advised – Rome traffic is chaotic, and parking is difficult.

---

Why I don’t recommend it as a day trip

Rome is enormous, intense, and endlessly layered. You could spend a week there and still feel like you’ve barely scratched the surface.

Trying to do Rome as a day trip is not just exhausting – it’s doing yourself (and the city) a disservice. You’d need to pick one or two major sights at most, and even then, it’s a lot: navigating crowds, queues, heat, and metro transfers. 

There’s no time to wander, to linger, to find the unexpected – and that’s where Rome often shines.

It’s also worth noting that Rome is better equipped than Venice to absorb short-term visitors, so the overtourism pressure is less extreme. But still – this isn’t a city that lends itself to light-touch travel. Go when you have at least three days to spare – I find four days to be the sweet spot. 

3 – Cinque Terre

How to get from Florence to the Cinque Terre

• By train: ~2h30 with changes – usually at Pisa and La Spezia, then onward to any of the five towns.
• Driving: ~2h15-3h depending on traffic. Cars aren’t allowed in most of the Cinque Terre villages, so you’ll need to park at the edge and walk or take the local train between towns.

---

Why I don’t recommend it as a day trip

The Cinque Terre is incredibly photogenic – and that’s part of the problem. It’s now one of Italy’s most overloaded tourist destinations, especially in summer, and most visitors arrive for just a few hours on a cruise or coach tour.

While a day trip from Florence is technically possible, it’s a long, complex journey that adds to an already unsustainable volume of footfall. Unless you’re willing to stay overnight or go completely off-season, I’d think twice.

If you are set on seeing it, I’d suggest only visiting one or two villages – and avoiding the midday peak. But for me, this is a place that’s been pushed to its limits. I’d rather visit somewhere that still feels balanced, not just beautiful.

Quick Comparison: Which Day Trip from Florence Is Best for You?

Destination	Best For	Travel Time (from Florence)	How to Get There	Tour Recommended?
Siena	Classic Tuscan city feel, medieval architecture	~1h15 by bus or ~1h30 by train	Bus or train	Optional
Bologna	Food lovers, cultural contrast to Florence	~40 mins by high-speed train	Train	Yes – Food tour
Arezzo	Renaissance history, frescoes, Vasari’s house	~1h by regional train	Train	No
Pisa	Half-day option, iconic tower, urban feel	~1h by regional train	Train	Optional
Lucca	Slow travel, cycling the walls, local feel	~1h20 by regional train	Train	No
Verona	Romantic riverfront city with Roman ruins	~1h30-2h by high-speed train	Train	No
Ferrara	Underrated Renaissance charm, affordable food	~1h15 by regional train	Train	No
Chianti	Wine tasting, countryside views, charming villages	~1h by car	Car or guided wine tour	Yes
Val d’Orcia	Rolling hills, Brunello wine towns, scenic drives	~1h45-2h+ by car	Car or small group tour	Yes
San Gimignano	Medieval towers, views, frescoes	~1h15 by car	Car or small group tour	Optional
Volterra	Quiet, well-preserved history, artisan shops	~1h45 by car	Car	No
Vinci + San Miniato	Leonardo’s roots, truffles, offbeat cultural detour	~1h by car	Car	Optional

Florence Day Trip FAQs

What’s the easiest day trip from Florence without a car?

The easiest day trips from Florence by public transport are those that are accessible by direct regional or high-speed trains. Bologna, Arezzo, Pisa, and Lucca are all reachable in under 90 minutes from Firenze SMN station and don’t require any transfers or complex logistics. 

If you’re nervous about navigating Italian transport for the first time, Bologna is especially straightforward – fast, frequent, and centrally located when you arrive.

---

Should I base myself in Florence and take day trips, or stay in smaller towns?

It depends on your travel style. Florence is a brilliant base if you love city life, cultural depth, and the idea of dipping into the countryside without repacking your bags every few nights. It works especially well if you’re travelling solo, don’t want to rent a car, or only want to do one or two day trips during your stay.

That said, if you’re dreaming of slow mornings on a terrace overlooking olive groves, or want to experience Tuscany without the crowds, staying in the countryside – particularly in Chianti or the Val d’Orcia – may be a better fit.

---

Is it worth renting a car in Florence for day trips?

If you plan to visit the countryside (like Chianti, Val d’Orcia, San Gimignano, Volterra, or Vinci), yes – renting a car is worth it. Florence is well connected by train, but rural Tuscany often requires driving, especially if you want to reach vineyards or smaller villages.

Just know that driving in and out of Florence’s city centre can be stressful if you’re not used to Italian cities. I recommend picking up your rental car from a depot just outside the centre (or at the airport) and choosing an estate car over an SUV if you need space – they’re more spacious and much easier to handle on narrow country roads.

---

Can I visit more than one Tuscan town in a single day?

Technically yes, but I usually don’t recommend it. Trying to fit in two or more towns in one day often means spending more time driving or transiting than actually enjoying where you are.

That said, if you’re visiting by car, you could combine San Gimignano and Volterra, or Vinci and San Miniato, in one day quite easily. Just keep in mind that part of the charm of Tuscany is not rushing – and most towns deserve more than just a fleeting stop.

---

Is Cinque Terre doable as a day trip from Florence?

It’s doable, but I don’t recommend it. The journey involves multiple transfers or a long drive, and it’s one of the most heavily overtouristed destinations in Italy. If you go, only try to visit one or two villages – not all five – and be mindful of the strain mass day-tripping places on small coastal communities.

For a more relaxed seaside experience, consider basing yourself elsewhere on the Ligurian coast and visiting Cinque Terre outside of peak hours.

---

What’s the best day trip from Florence if I want to visit a vineyard?

If wine tasting is your priority, Chianti is the most accessible option – you can either drive yourself or book a guided wine tour. For more serious wine lovers, Montalcino in the Val d’Orcia is the heartland of Brunello and offers a more immersive experience, but it’s much further and better suited to an overnight stay.

Do keep in mind that someone will need to skip tastings if you’re self-driving, so guided small-group tours are often the best solution.

---

Are guided tours from Florence worth it, or should I travel independently?

It depends on the destination. I’m a big fan of independent travel where it’s logistically simple – for example, places like Arezzo, Bologna, and Verona are straightforward to reach by train. 

But for places like Chianti, Val d’Orcia, or San Gimignano, where wine is involved or public transport is patchy, a small-group tour can be well worth it.

Look for tours that are locally led, capped at a small number of participants, and ideally visit one or two places rather than trying to squeeze in five.

Continue Planning Your Trip to Florence & Tuscany

Already excited to dive deeper into Florence and Tuscany? Whether you’re shaping your base itinerary or thinking about adding more time in the region, here are some next reads to help you plan.

Florence Travel Planning

• Ultimate Guide to Visiting Florence – the perfect starting point
• Where to Stay in Florence – neighbourhood guide + curated hotel picks
• 2-Day Florence Itinerary – see the highlights without rushing
• 3-Day Florence Itinerary – a more balanced experience with time to breathe
•  4-Day Florence Itinerary – ideal if you want to include a day trip
  

Exploring Tuscany

• Best Chianti Wine Tours from Florence – no car needed, just good wine
• One Day in Siena Itinerary – my personal route through this evocative hilltop city
• Best Towns in Tuscany – a curated list beyond the usual suspects
• Tuscany Road Trip Itinerary – for when you want to explore deeper
• Coming soon: Driving in Tuscany – what to know before you hit the road

You can also head back to the Florence Hub to browse every post at a glance – from cultural highlights to hidden gems and seasonal advice.

---