10 Days Tuscany Road Trip – Your Ultimate Itinerary

Italy is our fav country in Europe – or at least it’s in the top 3! One of the reasons we rate it so highly is that our Tuscany road trip was so magical. Driving through miles and miles of romantic scenery was an experience that we’ll never forget.

Renting a car in Tuscany is 100% recommended because it’s the only way to see the diversity of the region in a relatively short space of time. There’s the idyllic countryside of the Val d’Orcia, the incredibly preserved medieval villages of San Gimignano and Monteriggioni, and of course the vineyards of Chianti.

On a road trip, Tuscany reveals more of herself than you could possibly absorb just sticking to the major cities. Using our own personal experience, we’ve rejigged the route we took slightly to create an ideal itinerary that roams from Giotto’s Campanile to the hometown of Leonardo da Vinci – and a lot of other places in between!

Tuscany Road Trip: Overview

Day 1: Florence

All the best Tuscany road trips start in Florence, the cradle of the Renaissance. Boasting unforgettable architecture and one of the greatest art collections in the entire world, it’s also the main transport hub for the region.

If you’re flying into Florence, pick up the car after you’ve finished exploring the city to avoid the hassle of parking, which we’ve found to be quite expensive in Italy. For a similar reason, we’d recommend checking that all your accommodation offers free parking before booking.

⭐TOP PICK HOTEL IN FLORENCE WITH PARKING ➡️ Arte’ Boutique Hotel

⭐BEST BUDGET HOTEL IN FLORENCE WITH PARKING ➡️ Your Florence

📍 Start With An Ice Cream 🍦

There’s no better way to start a 10 day Tuscany itinerary than with a gelato! During our last trip, we ate one of these creamy frozen treats per day – when else do you get to indulge if not on holiday, am I right?

One of the best we had was at Venchi Cioccolato e Gelato, which is a super famous, fancy-looking place to go for Italy’s signature ice cream. Depending on the time of the day, you may need to queue a little, but it will be worth it, we promise! 

WHERE: Google Location

📍Grab A Coffee At Piazza Della Repubblica

With your gelato in hand, make your way slowly towards the Piazza della Repubblica, just round the corner. Back in Roman times, this was the centre of the city. Don’t expect to see any ancient or even medieval structures though, as almost everything here was rebuilt in the 19th century.

A carousel sits in the centre of the square, which is lined by several historic cafes that are stylish spots to get your morning cappuccino.

WHERE: Google Location

📍 Rub The Snout Of The Boar At Fontana del Porcelli

Fully caffeinated, make your way south along Via Calimala until you come to the Fontana del Porcelli, beside a souvenir market that has some lovely leather goods.

This bronze statue of a pig has a little bit of local lore associated with it: rubbing its nose is meant to ensure that you’ll return to Florence. It’s clearly been well thumbed, as the snout is super shiny, even though this cast of the original is only 16 years old.

People also slip coins in its mouth that, if they fall into the grate below, are meant to ensure good luck. Every little bit helps, right?

WHERE: Google Location

📍 Soak Up The Atmosphere Of Piazza Della Signoria

Piazza della Repubblica might have been the old town centre, but Piazza della Signoria is where it’s at today! Lined with buildings from the Renaissance, it’s a stunning place to take some photos and explore the multitude of statues in the Loggia dei Lanzi.

There’s even a replica of Michelangelo’s David here, though the real thing is not too far away in the Galleria dell’Accademia.

WHERE: Google Location

📍 Dazzle Your Eyes At Palazzo Vecchio

The most striking building in the Piazza Della Signoria is easily the Palazzo Vecchio. Built in the 15th century, it’s got funky crenelated walls and a big watch tower that you can ascend for panoramic views over the city.

The rooms have been lavishly decorated with frescoes and painting, especially the Salone dei Cinquecento (Hall of the Five Hundred). We actually got a neckache from gazing up for so long!

WHERE: Google Location

📍Grab A Sandwich At All’Antico Vinaio

For lunch, you can’t do better than All’Antico Vinaio. It’s one of the most famous sandwich shops in town – although ‘sandwich’ doesn’t really do justice to these mighty handfuls, which are stuffed with cured meat, mozzarella, and veggie spreads. There’s almost always a bit of a queue, but it moves fairly quickly. Eat outside proper ‘lunchtime’ if you can.

WHERE: Google Location

📍Take A Photo In A Historic Photobooth

One of the quirkier things to do on a visit to Florence is to get some snaps in one of the Fotoautomatica. These vintage photobooths are about half a century old, so it’s a bit of potluck as to whether they work or not. If you’re lucky enough to find a machine that is functioning, the black-and-white prints make for a really cute souvenir. 

We went to the one on Via del Proconsolo, next to the Badia Fiorentina abbey, which was busy but usable.

WHERE: Google Location

📍 View Masterpieces At The Uffizi

Among the most famous galleries in the world, the Uffizi is a must-see for every Florentine visitor, even if you don’t fancy yourself much of an art lover! Full to bursting with works by Michelangelo, da Vinci, Raphael, Caravaggio, Titian, and Botticelli, it’s basically a who’s who of all the greatest painters of the Renaissance.

We suggest booking a timed ticket in advance, so that you don’t waste time queuing outside. It is quite busy in the afternoons, so allocate plenty of time and arm yourself with patience!

WHERE: Google Location

📍 Dine At La Buchetta

Finish the first of your 10 days in Tuscany itinerary with dinner at La Buchetta, a short walk from the Uffizi. They’ve really nailed the vibe here, which is traditional neighbourhood trattoria meets upscale dining experience. We ate the classics here, including a good-sized portion of tagliatelle with wild boar ragu, followed by big old hunks of Florentine steak.

WHERE: Google Location

Day 2: Florence

Day 1 in Florence is mostly about taking in the atmosphere. Day 2 we’re getting down to some serious touring, starting with the city’s iconic cathedral.

📍 Visit Duomo First Thing In The Morning

With almost everything in Florence, the best way to avoid the worst of the crowds is to arrive as early as possible. That’s why we recommend seeing the Cattedrale di Santa Maria del Fiore – more commonly known just as the Duomo – at the very start of Day 2. Plus, the soft morning light is ideal for photography! 

From the marble façade to Filippo Brunelleschi’s iconic dome, it’s an incredibly beautiful building. It’s also free to enter, although you’ll need to pay and book a timed ticket in advance if you want to climb up into the cupola (highly recommended!) to see the interior frescoes up close and the view from the top. 

WHERE: Google Location

📍 Ascend the Campanile Di Giotto

Right next to the Duomo is Giotto’s Belltower, built in the 1300s at the same sort of time. Aside from being pretty, it’s a great vantage point to see the whole city, although we struggled to use our proper camera lens because the windows are barred.

We’d still recommend going up though, just make sure you book way in advance to secure a ticket at your desired time. 

WHERE: Google Location

📍 Cross The Ponte Vecchio

Constructed in the same century as the monuments around the Piazza del Duomo, the Ponte Vecchio is Florence’s oldest bridge. It’s not the most beautiful bridge in Italy by a long shot, but it’s an interesting piece of history, and you can cross it just as in medieval times, stopping to peruse the jewellery, antiques, and other souvenirs that line its sides.

WHERE: Google Location

📍 Lunch At Piazza De Pitti

Once you’re on the south bank of the Arno, it’s a short walk to the Piazza de Pitti with its enormous 15th-century palazzo. Before heading inside the palace, grab a bowl of pasta and an Aperol Spritz at one of the cafes in the square. 

We ate at Botteghina Caffe’ Pitti, but the neighbouring places also looked good.

📍 Experience Aristocratic Excess At Palazzo Pitti & Boboli Gardens

The Palazzo Pitti has been home to the most powerful families in Italy, from the Medici to the Italian royal house. As you can imagine, they left behind an impressive crib! 

The palace has been subdivided into various areas, including museums dedicated to fashion and art. The real treasure though is the building itself, which is just room upon room of opulence.

The powerful former residents obviously needed grounds to match the house, which is why they created an expansive parkland of fountains, tree-lined avenues, and grottoes, known as the Boboli Gardens.

WHERE: Google Location

📍Spend The Afternoon At Piazzale Michelangelo

Named for the of the Statue of David that lives here, the Piazzale Michelangelo offers the best panorama of Florence. If you ignore the crowds, it’s a lovely setting to enjoy the sunset.

WHERE: Google Location

Day 3: Wine Tasting Or Vespa Tour

Before you embark on your Tuscany road trip for real, we suggest taking advantage of one of the many tours that set off from Florence. 

📍 Gargle Chianti Wine

We can’t imagine road trips in Tuscany that don’t include at least one excursion into Chianti country. The trouble is that if you drive yourself, you won’t be able to try as much vino as you would like. Our solution? Go on a tour! 

The one we took trundled along the Chiantigiana, aka Chianti Road, stopping off at several wineries that grow Sangiovese grapes for plentiful tastings. We also learned a lot about the heritage of the wine-growing region from our friendly guide, who made the whole trip that much more fun.

📍 Hop On A Vespa

What’s a more Italian way of how to get around Tuscany than by Vespa? If you’re not a huge wine drinker, this tour through the Tuscan hills is an excellent alternative.

Setting off from downtown Florence, it covers the attractive hilltop Basilica di San Miniato and the suburban Medici home of Villa del Poggio Imperiale. Weaving through the campagna works up an appetite, even on a scooter, so the tour ends with lunch at a country estate.

Day 4: San Gimignano & Monteriggioni

Put Florence in your rearview mirror and head out into the countryside. The best road trip Tuscany has to offer is naturally going to include plenty of visits to gorgeous medieval towns, and San Gimignano and Monteriggioni are two that we would describe as unmissable. 

Start at San Gimignano, which is just over an hour from Florence. It’s quite a bit bigger than Monteriggioni, and you can easily spend 3-4 hours wandering the picturesque streets. We’ve not included everything there is to see here, just our fav bits.

📍 Enter San Gimignano Via Porta San Giovanni

San Gimignano has been protected since the 13th century by its sturdy stone walls. Its immediately recognisable in the distance thanks to its soaring tower houses, which were part of a war of one-upmanship by wealthy families. At one point there were more than 70, before the city authorities had enough and put a stop to the excessive building.

Visitors are not allowed to enter the city walls with a vehicle, but there are quite a few parking places just outside. We parked here, right outside the Porta San Giovanni.

WHERE: Google Location

📍 Travel Back In Time At Casa Campatelli

Many of San Gimignano’s towers have come down over the centuries, but 14 are still standing. One of these is the tower of Casa Campatelli, which we recommend as your first stop in the town. 

The top floor of the house hosts a video presentation that basically explains the history of San Gimignano, so you have a little background info as a guide before you go exploring. It was possible to climb the tower when we visited, and we also checked out some beautifully decorated rooms that show off how wealthy Tuscans lived in the 19th century. 

WHERE: Google Location

📍 Have A Gelato At Dondoli

There’s a gelato shop in San Gimignano that claims to have been in business since 1922. We don’t know whether that’s true, but it is where we got our daily scoop – and it was delicious! 

📍 Sit In The Piazza Del Duomo

With your ice cream in hand, wander over to the Piazza del Duomo and pop yourself down on the steps outside the church to enjoy your frozen treat. Sitting here, you’ll be surrounded by the towers of the town. 

If you want to climb one, buy a ticket for the Palazzo Comunale, which contains an art museum as well as access to San Gimignano’s tallest building, the Torre Grossa.

WHERE: Google Location

📍 Check Out Medieval Frescoes At Duomo Di Santa Maria Assunta

After you’ve snapped plenty of pics in the square, head into the duomo. The façade looks a little bland after the incredible churches of Florence, but inside its walls are fabulously frescoed. It’s hard to believe these paintings have been preserved with almost no restoration since the 1400s. 

WHERE: Google Location

📍 See The Views From Parco Della Rocca

Part of the joys of taking a road trip to Tuscany is the almost non-stop scenery. From the Parco della Rocca, we got a lovely panorama of San Gimignano amidst the rolling, vineyard-clad hills that surround it.

WHERE: Google Location

📍 Walk The Walls Of Monteriggioni

Monteriggioni might not have the distinctive towers of San Gimignano, but it’s a picture-perfect medieval walled town. Made up of just a handful of streets and buildings, it’s easily explored in just an hour or two, but the small size just adds to its charm.

An essential item on any Tuscany road trip itinerary, Monteriggioni’s 13th-century walls are still walkable in places, so you can experience the town from its battlements. There’s also a small museum dedicated to the armour of the Middle Ages attached to the tourism office.  

WHERE: Google Location

📍Eat Pasta At Antica Trattoria Papei

After Monterrigioni, drive to Siena and have dinner at Antica Trattoria Papei for amazing pasta. The portions are good, but the prices are great! It’s the perfect way to end Day 4 of our Tuscany road trip with a full belly.

Day 5: Siena

Siena once vied with Florence to be the most powerful and influential city-state in Tuscany. While it was eventually defeated and consumed by its rival, a lot of its former glory has been preserved through the ages, leading UNESCO to grant the historic centre World Heritage statue. 

Although you can see quite a bit of the city in a day, we found it an excellent base for day trips, which is why we recommend staying here for 3 nights.

⭐TOP PICK HOTEL IN SIENA WITH PARKING ➡️ Hotel Certosa Di Maggiano

⭐BEST BUDGET HOTEL IN SIENA WITH PARKING ➡️ Hotel Santa Caterina

📍 Roam The Piazza del Campo

Start Day 5 of your Tuscany roadtrip in the heart of town. The Piazza del Campo is probably one of the most memorable city squares in Italy. Paved with red brick laid in a fishbone pattern, it curves downwards towards the beefy-looking Palazzo Pubblico.

WHERE: Google Location

📍 Climb Torre Del Mangia

While part of the Palazzo Pubblico continues to serve the building’s original function as town hall, some of it has been converted into a museum. Here, you can see some stunning frescoes that cover the ceilings and walls of the huge rooms.

It’s also possible to climb the palace’s campanile, known as the Torre del Mangia. As you would kind of expect, the views from the top are jaw-dropping.

WHERE: Google Location

📍 Explore The Marvels Of Duomo Di Siena

A very short walk from the Piazza del Campo is the Piazza del Duomo, home to the city’s cathedral. 

The façade is mad enough, but the insides are another level of excess. Striped columns of black and white marble, statues by Donatello and Michelangelo, dazzling ceiling frescoes – each part of the cathedral has its own treasures to discover. 

Time your trip correctly and you’ll also get to see the incredible mosaic floors, which are only uncovered for a few months each year (usually summer and autumn).

Unlike most religious buildings in Italy, entrance is not free, and we’d suggest booking tickets in advance to avoid the queue. The number of people milling around was quite daunting when we visited, so try to go close to opening time if you want to beat the crowds.

TIP: For the best view of Duomo di Siena, climb Facciatone, which is an unfinished facade of a church right opposite the basiilica.

WHERE: Google Location

📍 See The Baptismal Font In The Battistero di San Giovanni Battista

The cathedral is composed of multiple areas, but you can basically buy one ticket and see them all. Make sure you don’t miss the baptistery, which has probably the most elaborate font we’ve ever seen, decorated with bronze and marble panels. 

WHERE: Google Location

📍 Lunch At Meet Life Cafè

We stumbled upon Meet Life Café completely by accident, but it was a great little find. Coffee and prices are good at this hole in the wall, which does a decent line in pastries and loaded focaccia.

WHERE: Google Location

📍 Stroll The Historic Streets Of Siena

Walk off your lunch with an exploration of the back streets of old Siena. The beautiful red of the bricks is so strongly associated with this city that it gives its name to a particular pigment that we remember from childhood boxes of crayons, Burnt Sienna.

Overall, we found Siena quieter than Florence, which made exploring the city a little more relaxing and leisurely.

📍 Santa Maria Della Scala

Make your way back towards the Piazza del Duomo to explore the former hospital of Santa Maria della Scala. Today, it’s a higgledy-piggledy museum with a random mix of historical and contemporary exhibits, with some areas still under renovation. We loved just getting lost wandering about the building, which is one big, glorious mess of a place with some gorgeous frescoes.

WHERE: Google Location

📍 Breach The Porta Camollia

Siena is one of the few major cities in Italy that still has an almost completely intact medieval wall. Porta Camollia was one of the most important entrances, and the defensive fortifications still look impervious today!

WHERE: Google Location

📍 Dinner At La Taverna di San Giuseppe

End the day in the charming caverns of La Taverna di San Giuseppe. It’s a beautiful space with a traditional Tuscan menu to match. They’ve got a top-notch selection of wine, which is stored in a cellar that dates to Etruscan times.

WHERE: Google Location

Day 6: Saturnia Hot Springs & Montepulciano 

Rise early and make the 2-hour drive from Siena to Saturnia Hot Springs, aiming to arrive by 9am. 

📍 Soak In The Saturnia Hot Springs

The best road trip in Tuscany needs to include a little downtime, and the thermal springs of Saturnia are a great place to relax. These sulphurous waters give off a slightly eggy smell but are said to be imbued with all kinds of healing properties. 

It was pretty busy when we were here, which is hardly surprising given that access is completely free, plus a ton of older locals seem to come here as part of a daily routine. Arriving early though will guarantee you a good spot for a soothing soak.

📍 Lunch In Montepulciano

After a couple of hours bathing in the natural spring and checking out the local town, drive for about 2 hours from Saturnia to Montepulciano for lunch. Famous for its wine, the hilltop town is a treasure trove of Renaissance architecture and easily one of the best places to visit in Tuscany by car.

We ate at the Osteria del Borgo, which has a hidden terrace at the back with awesome views of the campagna.

📍 Admire The Architecture Of Piazza Grande

After you’ve refuelled, head to the centre of Montepulciano. The Piazza Grande is up there with the most beautiful town squares we saw in Tuscany. Impressive palazzi and a rustic-looking cathedral (closed for renovation when we visited) surround the area, which contains an elaborately decorated well.

WHERE: Google Location

📍 Climb The Town Hall (Palazzo Comunale)

The Palazzo Comunale reminded us a bit of Florence’s Palazzo Vecchio in style. Its clocktower is the highest point in Montepulciano, even though it’s only 67 steps to the top – a mercifully short climb after the Campanile di Giotto!

WHERE: Google Location

📍 Stroll The Narrow Streets

As with many of the hilltop habitations of Tuscany, one of Montepulciano’s main attractions is just how picturesque the old streets are, with views over the countryside waiting around every curve. 

📍 Pulcinella Tower

A bit of a local curiosity, the Pulcinella Tower is topped with a statue of Punch (of Punch and Judy fame). Nobody seems to know why it’s here, but it sticks out like a sore thumb. Even after 300 years, Punch still strikes the bell on the hour.

WHERE: Google Location

📍 De’Ricci Winery

You can’t come to Montepulciano and not drink wine! There are quite a few wineries and bars to choose from, but we picked De’Ricci because of its dramatic old wine cellar. Tours are paired with tastings of either 3 or 6 wines.

WHERE: Google Location

📍 Sanctuary of the Madonna di San Biagio

Visit the sanctuary after leaving Montepulciano on your way back to Siena. Why someone would build such a decorative, expensive church here, we’ve no idea! It’s 100% worth a visit though, as both the outside and inside are lovely, even if there is a small charge for entry.

WHERE: Google Location

Day 7: Val d’Orcia Viewpoint & Volterra

After 3 nights in Siena, it’s time to move on. The next stop on our Tuscany road trip route is Pisa with its famous leaning tower, but there’s quite a bit to see on the way.

Taking a slightly circuitous route between Siena and Pisa, you’ll pass through the Val d’Orcia, which is basically the kind of countryside we imagine when we think of Tuscany. It’s all winding roads through rolling hills dotted with vineyards and cypress trees.

There are a couple of lovely towns we visited in the Val d’Orcia, including Pienza and Montalcino, but we haven’t included them in this road trip through Tuscany because we wanted to add Cinque Terre onto the end. If you’re not interested in visiting coastal Liguria, however, you can instead substitute an extra day in Siena and explore more of the valley.

📍 See Quintessential Tuscany From The Crete Senesi Viewpoint

One of the most famous roads in Tuscany runs through the Crete Senesi, which has a vista that belongs on every billboard advertising a trip to the region! There are multiple places you can stop to take pictures, but the location we’ve provided here was where we found the best views.

 WHERE: Google Location

📍 Journey Back in Time At The Acropoli Etrusca

En route to Pisa, stop in Volterra, a hilltop town which has been continuously inhabited since around the 8th century BC. There’s even evidence of early Etruscan civilisation in the form of the old acropolis. 

It’s mostly moss-covered ruins now, but we thought the underground cistern was pretty cool. We’d only visit though if you purchase the all-access Volterra Card, which includes the Etruscan Guarnacci Museum, as individual entry is a rip-off. 

WHERE: Google Location

📍 Climb The Tower House

Get the view of Volterra from above at this classic example of a Renaissance tower house. It’s not as tall as some of the ones we’ve already mentioned in other hilltop towns, but we quite liked the different perspective, as the roofs of the surrounding houses feel much closer.

WHERE: Google Location

📍 Admire The Luxurious Trappings Of The Palazzo Viti

Just a few houses down from the tower house, the Palazzo Viti may look medieval from the outside, but it’s decked out with all the luxuries of the 1800s on the inside. For fans of the great Italian director Luchino Visconti, his film Sandra was partly filmed here.

WHERE: Google Location

📍 Look Down On The Roman Theatre Of Volterra

Built in the first century BC, the Roman Theatre is a perfect ruin, the former seats of the auditorium claimed by moss. It’s a beautiful site, although we didn’t pay to go in as the free view from above is enough.

WHERE: Google Location

📍 Have A Drink On The Piazza Dei Priori

Surrounded by hundred-year-old buildings, the Piazza dei Priori oozes history from every nook and cranny. We didn’t’ end up going into any of the palazzi here, but it was nice just hanging out on the square at one of the local cafes (there are a few to choose from) with a cocktail.

WHERE: Google Location

📍 See The Ceiling Of The Cattedrale di Santa Maria Assunta

Just behind the plaza is the Volterra’s main cathedral. It’s worth popping in just to see the ceiling above the nave, which stands out in our memory despite the many churches we’ve visited in Tuscany. 

WHERE: Google Location

📍 Walk Through The Porta all’Arco

Before leaving town, make sure you stop by the old city gate of Porta all’Arco. It’s noteworthy because it’s another piece of old Etruscan architecture – although it’s been embellished and repaired over the years.

WHERE: Google Location

📍 Dinner At Ristorante La Buca In Pisa

Continue your road trip around Tuscany by driving an hour from Volterra to Pisa. One of the most underrated Tuscan cities, it’s worth spending at least one whole day here to experience the place, beginning with dinner! 

Even though it doesn’t look like much from the outside, La Buca is a bit of a hidden gem. The food was great, and the staff were incredibly warm. 

WHERE: Google Location

Day 8: Pisa

Pisa is famous for one very big thing: the Leaning Tower, which rises to a height of about 56 metres (183 feet) or 57 metres 186 (feet) – depending on which side is being measured! But that’s not the only thing the city has to offer, as we were very pleasantly surprised to discover.

⭐TOP PICK HOTEL IN PISA WITH PARKING ➡️ Palazzo Cini Luxury Rooms in Pisa

⭐BEST BUDGET HOTEL IN PISA WITH PARKING ➡️ The Rif – Boutique Hotel

📍 Marvel At The Piazza Dei Miracoli

Before we get into the less obvious attractions, we’ll begin with the place where most tourists congregate, the Piazza Dei Miracoli (Square of Miracles). One of the benefits of staying in Pisa is you can beat the daytime crowds, and it does get hella busy! 

Aside from the Tower of Pisa, the square is also home to a massive cathedral (the giant fresco of Jesus is miraculous), a very decorative cemetery (being around dead people never felt so glam), and a baptistery with incredible acoustics. 

WHERE: Google Location

📍 Escape The Crowds At Piazza dei Cavalieri

We never would have thought that such a remarkable plaza in such a popular Tuscan city would be so empty. It seems like most people only hit up the Piazza dei Miracoli and then leave town, skipping out on the Piazza dei Cavalieri (Square of Knights), the heart of historic Pisa.

The sgraffiti on the Palazzo della Carovana is amazing, but it’s also pretty cool just to be in an old piazza that feels like less of a tourist sinkhole.

WHERE: Google Location

📍 Stare In Awe At Chiesa di Santa Maria della Spina

Head south from the Piazza dei Cavalieri and cross the Ponte Solferino over the Arno River. Right next to the bridge on the south bank is a fabulous gothic church overloaded with exterior decoration. Given the spiky façade, it couldn’t be more appropriate that its name is the Church of St Mary of the Thorn!

WHERE: Google Location

📍 Pose In Front Of Palazzo Blu

There are quite a few palaces along the Arno River, but the Palazzo Blu sticks out because of its unorthodox paint job. Once you’ve posed for an Insta pic, pop inside to see the preserved old rooms as well as whatever modern art exhibition is on at the time.

WHERE: Google Location

📍 Lunch At L’Ostellino

Before leaving Pisa, cross back over the river and head to L’Ostellino for lunch. They stuffed our sandwiches very full here with charcuterie meats – the finocchiona is the best! There wasn’t any space to sit available when we went, so we just took our panini to go and parked up on a nearby bench.

WHERE: Google Location

📍 Dinner In Cinque Terre

Drive to Cinque Terre after lunch. It took us just under 2 hours, so you should arrive by about 4pm. That’s enough time to check into your hotel and get your bearings, before heading out to dinner. 

Technically speaking, Cinque Terre isn’t in Tuscany, but it’s close enough! Plus, it’s absolutely gorgeous and a fab locale to add onto a Tuscan road trip.

We stayed in Riomaggiore, a pretty town with colourful harbour houses that is the southernmost of the Cinque Terre. Our itinerary is based upon the assumption that you are starting here, but you can tinker around with it if you find a hotel that catches your fancy in one of the other towns.

For our first night, we dined at Bar e Vini a Pié de Ma – and yes, we picked it for the view, which is 5 stars! 

WHERE: Google Location

Day 9: Cinque Terre

The five villages that make up Cinque Terre are all scenically perched on cliffs that slide down towards the sea. Each one has its own flavour, from clifftop Corniglia to beachy Monterosso. Driving around Cinque Terre can be a bit of a nightmare, so we’d suggest ditchign the car in favour of trains and hikes.

Have an early breakfast, then take the train from Riomaggiore to Monterosso al Mare at 8am.

⭐TOP PICK HOTEL IN RIOMAGGIORE WITH PARKING ➡️ The Upper House

⭐BEST BUDGET HOTEL IN RIOMAGGIORE WITH PARKING ➡️ Al castello

📍 Hike From Monterosso To Vernazza

Monterosso is the largest of the Cinque Terre and is best known for having sandy shoreline. For us, it’s one of the less interesting villages because its appeal is mainly about the beach, though the Statua del Gigante is a fun thing to check out. 

From Monterosso, it’s about a 1.5-hour hike to the next village along, Vernazza. The countryside surrounding the Cinque Terre is stunning, and there are lots of places along the route that you’ll want to stop and just admire the scenery. 

📍 Visit Vernazza

There’s a mind-blowing view of Vernazza from above towards the end of the hike that really sums up the charm of the village. It was very busy here when we visited, but it’s hardly surprising given the picture-postcard perfection. Grab a gelato and chill out by the harbour, before continuing your hike.

Don’t forget to pick up some extra water before you leave! 

📍 Hike From Vernazza To Corniglia

Hike for an hour to Corniglia, the only one of the Cinque Terre not on the sea. Instead, it’s sprawled across the top of a cliff. If people are going to skip one of the ‘Five Lands,’ they usually skip this one, but to be honest we enjoyed the different style and feel of the place.

📍 Lunch In Corniglia

Corniglia is the smallest of the Cinque Terre and seems to be the least popular, judging by the size of the crowds. That’s part of what made it a nice place to stop for lunch. For such a small place, there are a ton of options, but we picked A Cantina da Mananan, a super cute backstreet eatery where they cram you in – which is surprisingly convivial, rather than stuffy!

 WHERE: Google Location

📍 Hop On the Train Back To Riomaggiore

There’s a notorious set of stairs leading from the train station of Corniglia up to the village of Corniglia called the Scalinata Lardarina. If you follow our itinerary, however, you’ll be going down them rather than up – and from the look of the sweating faces of the people we passed on the way, we picked the right direction!

📍 Dinner At Manarola

We were pretty exhausted after all the hiking, so we holed up in our hotel for a little siesta, before freshening up for our last stop, Manarola. This village is most famous for its wine – although to be honest we had pretty good vino everywhere in the Cinque Terre. 

Again, we were drawn by the view to Nessun Dorma, which was a lovely place to watch the sunset. The food is 100% overpriced, but the vibe is A+ romantic.

WHERE: Google Location

Day 10 Visit Vinci & Return The Car

The last stop on our Tuscany road trip is the town of Vinci, famous for being – you guessed it – the birthplace of the Leonardo! It’s only a short stop off en route back to Florence.

📍 Explore The Home Of Leonardo da Vinci

Located outside the town of Vinci, up in the hills, the house where Leonardo da Vinci was born is a spine-tingling piece of history. There’s not exactly much to see, but just thinking about the fact that this dude lived here once gave us chills!

WHERE: Google Location

📍 Leonardo da Vinci Museum

You can get a combined ticket that gives you access to Da Vinci’s birthplace as well as museums in the main town of Vinci that examine his painting and his inventions. There’s also a tower can ascend to for views over the surrounding countryside.

WHERE: Google Location

And that’s the end of our Tuscany road trip! 

Depending on where you fly out from, you can either drive to Florence or Rome to return the car. Dropping off a hire vehicle in a different location can entail additional costs, but it may be worth it logistically, depending on your forward plans. 

You could even continue for longer in Italy, if you’ve got enough holiday time cached! 

FAQs

How many days for a Tuscany road trip?

From our experience, we’d say a Tuscany 10 day itinerary is a good amount of time to explore the region. We visited all the places mentioned here over the course of multiple smaller trips, but if you want to see as much as possible in one go, this 10-day schedule is how we’d do it.

What is the best time of year to go to Tuscany?

For mild to warm weather, aim for May, June, or September. Avoid July and August if you can because those are the busiest months of the year. Florence in particular can be busy at the best of times, and peak summer can be a little draining in a sea of people.

Is driving in Tuscany difficult?

Getting around Tuscany is mostly pretty easy. You do have to watch out for restricted traffic zones (ZTLs), where only residents are allowed to drive. These are mostly in the old city centres, but make sure you check your route beforehand to avoid annoying fines.

Is it worth hiring a car in Tuscany?

Yes, it’s definitely worth hiring a car in Tuscany. Exploring the rolling countryside and visiting the scattered medieval villages is impossible using public transport and much more costly/ time consuming via tour. If you only want to stick to the main cities though, there is a robust railway network in place.

Final Word

There’s no such things as the best Tuscany road trip because there are lots of different routes through the region that are equally splendid. For example, on our most recent Italy trip, we flew into Rome and drove up through the Val d’Orcia, lolling about in Chianti for a few days, before eventually ending up in Florence. It just depends on what kind of holiday you want to have, whether it’s city tripping, wine tasting, or slow travelling through Renaissance-era towns.