Tuscany is made for a road trip. It’s one of those places where the drives are just as lovely as the destinations; rolling hills, olive groves and tiny villages you stumble into without meaning to.

We didn’t stick strictly to Tuscany the whole time, but everything we did had that same vibe: good food, beautiful scenery, and a slower pace of life.

There’s loads you could pack into a trip here, but this is how we spent our nine days. And honestly, we wouldn’t change a thing. It was the perfect mix of proper Tuscan living and incredible eating. If you're thinking of doing something similar, here’s a little peek at how we did it.

Modena
Maranello
Florence
Arezzo
Montepulciano
Pienza
San Gimignano
Lucca
Bologna

Overview and Map

Driving tips

Driving around Tuscany is actually pretty easy once you're out of the cities. The countryside roads are scenic, quiet, and often feel like something out of a film (because a lot of them are). That said, there are a few things worth knowing before you set off, especially when it comes to parking and avoiding fines.

Blue lines = Paid parking. You’ll need to find the nearest machine and pay, usually by the hour. Keep the ticket visible on your dashboard.
White lines = Free parking (rare but glorious when you find it). Just double-check for any nearby signs to make sure it’s not resident-only.
ZTLs (Zona a Traffico Limitato) – These are restricted traffic zones in most towns and cities. Avoid at all costs unless you’re 100% sure you’re allowed in. They’re usually marked by a sign with a red circle and a camera icon. You can get fined just for driving through one, even for a few seconds. YOU CAN EASILY GET CAUGHT OUT BY THESE so be very vigilant when approaching cities. Often, if you take the wrong turn down a one-way road you can see the ZTL zone coming up and there is nothing you can do about it.
Parking charges vary a lot. In busier towns, expect to pay €1–€2 per hour, sometimes more. Bring coins becuase it’s a pain when the machine doesn’t take card or app payments.
Park outside the old towns to avoid charges and walk in them. They are all pretty small so you can take your baggae with you. Except in Florence, where you can park at a car park in the city and get an exemption from the hotel

We usually rent through AVIS, as our Amex Platinum card includes benefits like a second driver at no extra cost and guaranteed upgrades, which makes the experience smoother and often better value overall. However, for this trip we used Trip.com and paid £139 for the full 9 days and an extra €64 to add a second driver. The car hire was run through Italy Car Rent.

Why we think the Amex Platinum Card is worth £650

General Tips About Tuscany

Plan around local timings – Most towns shut down in the afternoon, especially between 2–4pm. If you’re hoping to have lunch somewhere, aim to arrive by 1 pm latest or you’ll likely miss the kitchen window.
Embrace the slow pace – Life in Tuscany moves gently. Don’t expect quick service or tightly packed itineraries to work out. It’s all part of the charm.
Brush up on Italian coffee culture – Don’t expect flat whites and caramel lattes. Coffee is a quick, standing affair (blog post about this coming soon!).
Seek out local trattorias – The best meals are often found at simple, family-run trattorias. They offer honest, regional cooking at great value (we’ll be sharing a guide soon on the different types of Italian restaurants).
Taste your way through Tuscany's pasta – Each town often has its traditional pasta shape or local speciality. Try them all – it’s one of the best ways to experience the region’s diversity.

The Road Trip

We started extremely early in London (4 am pick up), and our flight was to Bologna Airport. Yes, our Tuscan road trip is actually starting off in Emilia-Romagna, but we’ll just let that slide for now!

Day 1 - Bologna Airport > Modena

40 mins drive

After waiting around 90 minutes to pick up our hire car at Bologna Airport (welcome to Italy), we eventually hit the road and drove straight to Modena. Google Maps will try to take you via the toll road, which is a bit faster; however, we took the straight road that goes through a few small towns because we love passing through lesser-known places and seeing what everyday life looks like.

We arrived in Modena around 3 pm, which, classic Italy, meant everything was shut. It’s the same in most towns. Shops and restaurants close for a few hours in the afternoon, so don’t expect to do much until things start reopening for aperitivo.

Modena is small but full of character, and as a proper foodie town, it’s a fun one to just explore on foot. We had a coffee in a lovely little café right by the main square, talking to the owner and getting her tips for Florence.

We also walked past the legendary Osteria Francescana—you can’t visit Modena without at least seeing it. We peered through the glass and could actually spot the kitchen and part of the dining room. One day, we’ll be back to eat there properly… fingers crossed!

Parking | A garage called Ferrari

Food | Lunch at the only open place we found outside our AirBnb (Focaccia and potatoes) and dinner at Frencesetta 58, the sister restaurant to Osteria Francescana (sadly it was pretty average).

Culture | Watch the first couple of episodes of ‘Master of None’ season 2 on Netflix, it’s based in Modena

Day 2 - Modena > Maranello > Florence

30 minutes drive to Maranello and then a 2-hour drive to Florence

Modena

We started the morning with a proper stroll through Modena’s market, and it did not disappoint. The produce was unreal. Giant wheels of cheese, glistening fruit, fresh pasta, herbs, meats... the kind of place where you instantly wish you had a kitchen to cook in.

We picked up a flaky lobster tail pastry filled with pistachio cream, which was just ridiculous—sweet, crunchy, creamy, everything.

Next up was a balsamic vinegar tour with Acetaia San Matteo, just outside town. It’s a small, family-run place, and honestly, one of the highlights of the trip. Sandra, who runs the tour, was full of knowledge and warmth.

We learnt all about how traditional balsamic is made (spoiler: it takes 25 years) and how it’s aged in different barrels in the attic, so it’s exposed to the extremes of the seasons. There’ll be a full post on this coming, because it was genuinely fascinating and worth doing if you’re in the area.

Maranello

From there, we drove to Maranello—because obviously, if you love Formula 1, you have to. Quick lunch stop at Ristorante Montana, which has major Ferrari history. Michael Schumacher used to eat here all the time, and the place is filled with memorabilia (I’m guessing Lewis Hamilton will be a regular here now too!) The pasta was great, service warm, and the kind of place you can tell is special to locals and Ferrari fans alike.

Then onto the Ferrari Museum, which we explored for about 90 minutes. Loads to see and take in—even if you’re not an F1 obsessive, it’s impressive. That said, skip the simulator. It’s €30 and really not worth it for the time you get on it.

Florence

We hit the road to Florence in the late afternoon, but got stuck in a bit of traffic and delays, and the arrival into the city was… chaotic. Florence is beautiful but an absolute maze to drive through. We eventually parked up in a garage near our Airbnb and ditched the car, ready to explore on foot.

And walking is where Florence shines. It’s a big city, but it's also extremely walkable. We wandered past statues, down side streets, through buzzing piazzas and caught a stunning sunset by the river.

Dinner was at O’Munaciello, a pizzeria set in an old convent. Wood-fired, proper Neapolitan pizza, and everything we ate was spot-on. Cosy interior, great service, and just a really lovely place to eat.

On the way back, we grabbed a gelato from a random spot, and it ended up being one of the best of the trip.

Parking in Florence | Florence has a ZTL (Zona a Traffico Limitato) in the historic centre, but if you’re parking in a central garage, they can actually register your number plate with the authorities to exempt you from the fine. You’re not allowed to drive around but it gives you a grace period to enter and exit the city. Make sure you book a garage ahead and confirm they’ll report your plate. We used one just around the corner from our Airbnb, and they sorted it for us—no stress.

Day 3 - Florence

We didn’t sleep all that well, thanks to a very rowdy 3.30 am crowd outside our flat – Florence clearly parties late. Earplugs turned out to be a godsend.

Still, we were up by 8:30ish and ready to make the most of the day. Alice went for a morning run, and I set off on the same route, stopping every few minutes to snap pictures. Florence really is ridiculously photogenic.

After getting ready and some morning pastries, we joined the queue at All’Antico Vinaio – Florence’s cult sandwich shop. The line looked wild, but it moved fast. We shared The Italian and Beatrice, both packed with flavour and truly deserving of the hype. We found a sunny spot by the river to devour them, fending off a few persistent pigeons along the way.

We strolled through a few galleries before hunting down the affogato spot Alice had been eyeing – Vivoli. Another queue, but again, absolutely worth it. Possibly the best affogato we’ve ever had.

In the afternoon, we wandered around the Santa Croce neighbourhood – a little quieter and more local in feel. We popped into a small restaurant called C.R.U and ended up booking a cooking class with the head chef, Gabriel, and chatted through some of his food and wine recommendations.

Florence’s leather school was an unexpected gem with high-quality goods on offer.

We made the walk up to Piazzale Michelangelo for the classic sunset view. Slightly hazy skies, but still a stunner. Aperols in hand, we soaked it in.

After a quick stop home, we went out again for drinks at a wine bar we stumbled across called Il Santino – low-key but excellent.

Dinner was at Il Latini, a spot we’d booked in advance. The meal itself was solid, though Florence’s famed Florentine steak, if we’re being honest, always feels a bit underwhelming (I just don’t think it’s the best way to cook a big piece of steak). Still, the atmosphere was buzzing.

Day 4 - Florence > Viesca Toscana

40 minute drive

We were up early – 6:00 a.m. – for a sunrise run and some photography. The light was soft and golden, and just as we reached the river, a few hot air balloons floated into the sky. It was completely magical and one of those fleeting travel moments that just sticks with you.

Back at the flat, we packed up and left our luggage in the car park. We grabbed a quick coffee before our much-anticipated cooking class (which was absolutely incredible, see the video below) and then wandered back through the Santa Croce neighbourhood, picking up a few bits at the market and stopping for a decent flat white at a café called Coffee Mantra.

The drive to Viesca Toscana was short but scenic, and as soon as we arrived, we knew we were in for something special. The property is absolutely stunning – Tuscan countryside perfection. We were both knackered, though, so after checking in, we collapsed by the pool to decompress. While we were lying there, two massive snakes appeared in the grass nearby – either fighting or mating (hard to tell), but it was wild to watch.

After a nap and a scoop of ridiculously good (but also ridiculously expensive) chocolate and hazelnut gelato, we started getting ready for dinner. The hotel meal was really good, served in a lovely quiet setting, and we were back in the room within the hour.

Day 5 - Viesca Toscana | Arezzo

45 minute drive to Arrezo

After a morning run for Alice and a gym session for me, we borrowed bikes from the hotel and headed out for a ride, which quickly turned into us just getting completely lost in the Tuscan hills. Back at the hotel, we cooled off with a swim and spent the rest of the afternoon sunning ourselves by the pool and enjoying the spa.

After freshening up, we had a chat with the lovely hotel staff who recommended Arezzo for the evening. The drive was smooth, and parking was free after 8 pm. There’s even a series of escalators that take you up to the old town – like a Tuscan ski lift.

Arezzo was very stylish. Turns out there was an aperitivo event happening at a place called SUGAR, and it seemed like the entire fashionable population of Tuscany had turned up. Behind the church, we found stunning views over the valley.

We stopped for an Aperol at a bar and shared focaccia with salty bresaola. Then made our way to Il Saraceno, a trattoria listed in the 2008 Michelin guide. No frills, no music, and barely any English spoken, which made it all the more charming. The pasta was top tier. I had a rabbit ragu with pici, and Alice went for pappardelle with wild boar. The tiramisu at the end was next level. Probably the best one we had on the whole trip – the cream was almost mousse-like. The house Chianti was excellent too, from nearby Arezzo vineyards.

Day 6 - Viesca Toscana > Montepulcianno > Pienza > San Gimignano

3 hours of driving total | Our Wedding Anniversary

We woke up bright and early at 7.15 for a yoga session overlooking the Tuscan countryside, hosted at Debbie’s villa in Viesca. She’s a yoga teacher from Bristol, her husband from New York, and together they’ve created the kind of retreat you picture when dreaming of a slower life in Italy. They’re Sting fans too – apparently his villa and pizzeria are just 15 minutes down the road.

Monepulciano

We headed for Montepulciano becuase it looks stunning and it didn’t disappoint. Free parking just outside the town walls made the uphill walk worth it. It’s steep, but the views from the top were spectacular. I grabbed a random pizza slice on the way back down – priorities.

Pienza

Next stop: Pienza, the village famous for pecorino cheese and postcard-perfect charm. We had lunch at Latte di Luna, where the cacio e pepe pici and lasagne were both absolute standouts. The lasagne was made from folded fresh pasta sheets with just enough bechamel and bolognese in between – a method we’re now stealing. The cheeses were strong and punchy in their flavour.

This lunch was the best pasta meal we have ever had!

We continued the drive through the Val d’Orcia (the famous postcard road of Tuscany, and near where gladitor was filmed), deliberately avoiding toll roads to soak in the rolling hills and iconic Tuscan landscapes.

San Gimignano

There is a 15-minute drop-off zone outside the city walls for you to leave your luggage off before finding a parking spot. Naturally, we drove into a ZTL zone by mistake, we’ll see what fine rolls in. Bags dropped, car parked, we quickly freshened up and made it to the hilltop viewpoint just in time for a quiet sunset.

We found a table at Osteria I Quattro Gatti. They were short-staffed (only two cats working), but the garden setting was gorgeous.

Zaeem loved the chocolate cheesecake, and the pici aglio was excellent – garlicky, simple, and spot-on. The porcini mushroom tagliatelle was a bit bland in flavour, but the pasta itself was lovely. A small bottle of Chianti made it all feel right.

Day 7 - San Gimignano > Lucca

1 hour and 30 minute drive

We grabbed a coffee and pastry at the place opposite our Airbnb before wandering back into a linen shop we’d spotted the day before. Alice picked up a beautiful outfit, and I walked out with a new shirt.

We made the decision to head straight for Lucca (the original plan was to go via Siena), taking the scenic country roads instead of the motorway. A surprise road closure threw a spanner in the works, and after multiple failed detours (and some rising tensions in the car), we finally made it in.

We parked right inside the city walls at a central car park – triple-checked it wasn’t in the ZTL – and made our way to check in.

Lunch was at Trattoria da Giulio, a classic under-the-arches spot with local dishes at very non-touristy prices.

Gnocchi with gorgonzola and walnuts – soft, creamy, punchy.
Panzanella – a great reminder of how simple ingredients can be magic when done right.
Tordelli Lucchese – meat-filled pasta parcels with a rich ragu.

We rented bikes and cycled around the entire city wall – such a fun way to explore. We stopped in one of the piazzas for a glass of wine and a moment to soak in the golden-hour glow.

Dinner was at a place we think was called Osteria Dal Manzo. The service was brilliant – warm and genuine – and the food was solid:

I had a tagliata, perfectly cooked with a well-dressed salad.
Alice went for a pasta dish that leaned more stew than sauce, hearty and full of depth.
Tiramisu was a dream – maybe the best we had on the trip.
We also tried a Portuguese milk tart, which was fine but forgettable.

Day 8 – Lucca > Bologna

2-hour drive

We found a cosy café with covered seating under the city’s signature arches and sipped our morning coffee while people-watching. A quick wander through a few shops, then back to the flat for another coffee brewed in the moka pot and some time flicking through the L’Artusi cookbook – a calm, easy start to the day.

We packed up the car and started the drive to Bologna, ditching our original plan to stop in Pisa after reading far too many reviews about car break-ins.

We managed to park right outside our Airbnb as were staying closer to the airport than the city.

Our first stop was the Mercato delle Erbe – a beautiful old market, though most of the stalls were closed by the time we arrived. We stumbled across Bar Senza Nome, a café run by deaf people, where you can learn sign language, which was a brilliant experience.

Bologna itself is grand, with wide arcades, terracotta buildings, and a buzzier city feel than the Tuscan towns we’d come from. We reached the central square, wandered through a few shops, and tried to find a proper Bolognese to eat but we were stuck in the trap of arriving in an Italian town at 3 pm, nothing was open. We did find one pasta restaurant open, and I think it was one of the worst Bolognese I've had in my life! How ironic.

In the evening, we tried to get a table at Trattoria da Cesari (highly recommended), but they were fully booked thanks to a group of 65 taking over the place. Luckily, we got into La Taverna Dei Peccati just around the corner.

Before dinner, we dropped into Enoteca Italiana – packed with older Italians sipping wine, chatting, and people-watching. A proper local spot. We picked up a bottle to take home after having a delicious Parmigiana di Melanzane.

Dinner was a slight redemption. The ragu here was actually very good – rich and comforting, though the tortellini in sage butter and tiramisu were both average. The tiramisu, in particular, was far too soaked, with the coffee overwhelming everything else.

Day 9 – Heading Home

And just like that, our Tuscany adventure came to an end.

We had a slow start to the morning – neither of us had slept particularly well, and the travel fatigue had definitely kicked in. We packed up our bags one last time, loaded up the car, and made our way to the airport.

Our 9-Day Tuscan Road Trip: Itinerary and Journal