Certaldo - The Perfect Base for Car-Free Tuscan Travel

Tuscany is beautiful. Tuscany is historic. Tuscany is also, for most of summer, a bloody nightmare to drive in, especially if you're short on time and patience.

Nestled between Florence and Siena, Certaldo offers all of the first two statements above while solving the problem of the third.

Perched strategically on the train line between Florence, Siena and Pisa, Certaldo is the rare kind of place that offers everything you'd want in a Tuscan holiday.  It has wonderfully walkable medieval streets, sensational food, cultural depth, and sweeping views and an ideal base for car-free Tuscan travel.  There are few better places on Earth to catch the sweeping sunsets - see above image for proof - with a glass of Chianti in hand.

I’m hardly neutral when it comes to Certaldo. As soon as borders reopened in the summer of 2020,

I booked the first flight to Pisa and chose Certaldo purely for its location.  

By sundown, I was standing on Via Boccaccio with a Hugo Spritz in hand, watching the golden light turn the medieval brickwork to a dark shade of honey.  That was it, I was hooked.  Since then, I’ve returned three times and commended this town to anyone who asks (and plenty who don’t).

If you’re reading this, congratulations - you’re now one of them. Certaldo really is that good.

A Town with History (and a Funicular)

Certaldo may not scream for attention, but it really warrnts .it The area was settled by Etruscans and Romans, and the fortified upper town flourished in the Middle Ages under Florentine rule. Its most famous resident, Giovanni Boccaccio, was born here in 1313. Best known for The Decameron (yep, that hammy Netflix series was based on 700 year old text - think an Italian Canterbury Tales but considerably more exciting), Boccaccio remains a central part of the town’s identity.  You’ll see his name on everything from street signs to gelato shops.

Certaldo is split into two parts: the modern lower town (Certaldo Basso) with the train station, shops, and services, and the older Certaldo Alto, a gorgeous hilltop medieval town that looks like it was built for a period drama and then never changed. You can walk up, but it’s far more fun – and easier on your legs - to take the funicular, a charming cable railway that connects the two towns in under two minutes.

The funicular runs daily from 7:30am to 8:00pm (until 1:00am during festivals like Mercantia) and costs €1.50 each way or €2.50 return. It’s a small thing, but it makes a big difference: hop on, ride up, and step directly into the 13th century, no horse required.

Getting Around Without a Car

Certaldo’s greatest strength is how easy it is to reach everything without driving. It’s on a direct rail line with:

• Florence (55 minutes, direct)

• Siena (45 minutes, direct)

• Pisa (75 minutes, one easy change at Empoli)

• Poggibonsi (15 minutes), where you can catch a local bus to San Gimignano (view from Certaldo Alto pictured) - journey time just under an hour total

The trains are frequent, reliable, and scenic. You can easily plan day trips to major cities, explore art galleries and markets, then come back to your base in a quieter, more relaxing town where the trattorias aren’t packed with bus tours.

Beyond being a great base for Tuscany’s big three, what else does Certaldo offer?  A fair bit actually.

Step Back In Time

Once in Certaldo Alto, you’ll find yourself surrounded by terracotta buildings, cobbled lanes, and panoramic views across the Val d’Elsa that haven't changed much since Boccacio's era You don’t need a map, just follow your eyes - or at lunchtime, your nose.

Unusually Certaldo Alto doesn’t have a single main square, scattering shops and restaurants between atmospheric streets, most of which line Via Boccacio.  The focal point – and a must-visit – at the end of this lane is the Palazzo Pretorio (pictured), a 12th-century fortress-palace that once housed Florentine magistrates. The building itself is a work of art, with family crests on the facade and original frescoes, courtrooms, and even a prison cell inside with medieval grafitti.

Just down the lane is the House of Boccaccio, now a museum with period furniture, old manuscripts, and occasional literary events. Even if you’re not a medieval literature buff, it’s fascinating to see how much of the old structure remains and how deeply the town celebrates its native son. 

Climb the tower for even more sweeping views – on a clear day, the silhouette of San Gimignano is the literal medieval Manhattan all the guidebooks tell you about.

Eating (Very) Well in Certaldo

To say Tuscany is known for its food is a gross understatement.  Certaldo delivers all of the flavour whilst allowing visitors to swerve the dual traps of unnecessary pretension and tourist-trap ‘menus in six languages’ debacles. Here, the menus are seasonal, the wine is local, and the staff usually knows the vineyard personally.

Start with Osteria da Chichibio, a traditional trattoria set just below the Palazzo Pretorio.

Their pappardelle al cinghiale (wild boar pasta, pictured) and local cheese plates are gold star, best-in-show delicious. If you’re lucky enough to get a seat outside, you’ll also score highly for people watching and the live music which often springs up on a summer’s evening

For something more refined, book a table at Osteria del Vicario, housed in a former rectory with a warm, rustic interior and carefully crafted Tuscan dishes. Highlights include truffle tagliolini and grilled lamb with rosemary, all paired with regional wines. Move down the street to any of the bars which dot Via Boccacio for a spritz and to continue people-watching.

Once you’re done, you are required by law (well, you should be) to fare una passeggiata (take a stroll) through the streets, which come to life as the sun descends. You’ll doubtless be in the mood for gelato. 

Pistachio?  Dark chocolate?  Onion?

Ah yes, the onion gelato. Certaldo is famous for its sweet and mild red onions are sweet (you can buy it in sweet and savour preserve form everywhere in town) and Gelateria di Bracali Patrizia (also on Via Boccacio) has decided to go one step further. It’s subtly savoury albeit not to everyone’s taste.   If you’ve already descended on the funicular, Ma Ke gelato is one of the best rated in the whole region (and with good reason)

But Oh, Those Summer Nights

Certaldo doesn’t sleep through the summer - it sings. The biggest event is Mercantia, a week-long street theatre and arts festival in July. By night, the usually peaceful Certaldo Alto it transforms into a glowing, candlelit carnival of musicians, fire jugglers, acrobats, and surreal performances tucked into every alley and archway. The atmosphere is electric but intimate, no massive stages, just spontaneous wonder.  Elsewhere open-air cinema evenings in the grounds of Palazzo Pretorio and live jazz on the streets for Ferragosto (15th August) add a sprinkle of magic…not that the landscape needs it.

Outside of Mercantia, there’s plenty happening on a smaller scale. Live music often echoes through Piazza SS. Jacopo e Filippo, and local artisans sell their wares during weekly markets in Certaldo Basso.  July also sees a weekly night market where handmade leather goods, linens, wine, olive oil, cheese, and the occasional accordion serenade jostle for prime position.

When You Might Just Want a Car

Having made a big deal of the car-free delights of Certaldo as a base, there are some scenarios where your own four wheels is useful.

Wineries dot the landscape around the town – half the fun is seeing a sign and spontaneously pulling over.   We were privileged to find Tintichainti (pictured), which offers delectable wine and olive oil tasting with accompanying food platters.  The landscape, the enthusiasm from our host Daniel and the frankly outstanding Chianti made us channel our inner Frances Mayes and start looking at nearby farmhouses to renovate!

Hiking around the town is also easier with your own car. The Via Francigena, an ancient pilgrim trail to Rome, passes nearby. Several sections are walkable from Certaldo, but if you want to access more remote stretches or circular routes, having a car makes it easier.

If you do have a car, there is a spacious car park just below Certaldo Alto (don’t even think of trying to drive down the narrow streets), just follow the signs for Certaldo Alto.

Everything Under The Sun

For independent travellers who would rather avoid the worst excesses of Tuscany, Certaldo offers the perfect blend of authenticity and ease. You can wake up to birdsong and church bells, spend your day wandering world-class cities or vineyard trails and return in the evening to a sensational dinner and sunset cocktails, the memory of which will see you through many a long winter night.

No car. No crowds. No stress.  All that you ever dreamed of when you think of Tuscany, all on your own terms.