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There is a true romance to Tuscany in spring. As the region begins to exit its winter hibernation, its towns and countryside burst into life.
Its rolling hills become vivaciously green, roadsides and hedgerows see an explosion of fragrant poppies and roses and the sound of chatter and footsteps begin to spill out into the piazza of its many towns and villages. It is a choice time to embark on a Tuscan road trip.
Many are drawn to explore Italy in summer, but Tuscany is a romantic region that begs to be discovered under the soft light of springtime and we were more than happy to oblige.
In spring, as daylight hours begin to creep up so too do Tuscany’s temperatures, lending to perfect road trip conditions for you to lose yourself in the Tuscan countryside.
Touring Tuscany can present its challenges – mainly in that there are a myriad of places that you could visit and fall in love with, but it is nigh impossible to fit all of these into one trip to Tuscany (unless, that is, you have weeks to spend there).
I personally spent 10 days in Tuscany and would happily have spent ten days more had circumstances allowed it.
Our journey commenced at the beginning of it all – the Cradle of the Renaissance – where we happily drowned ourselves in a sea of Michelangelo, Botticelli and da Vinci in Florence.
We gazed in wonderment at Brunellschi’s dome, grandiose talisman that has dominated the skyline of Florence for more than half a millennium.
We walked hand in hand under the wisteria-clad trellises of the Bardini Gardens and devoured gelato at twilight by the river Arno, having watched the sun turn the walls of the Ponte Vecchio vivid shades of amber and ochre at sunset.
And then, when we had our fill, we picked up our rental car and thus began in earnest our Tuscany road trip.
Our Italian road trip took us first to the hills of Chianti, where we enconced ourselves in a Tuscan villa complete with vineyard and familiarised ourselves with the delectable Chianti produced at their winery.
We then ventured our way further into Tuscany, where we settled ourselves in the shadow of the great walls of Montepulciano and discovered the unparalleled landscape of the Val d’Orcia. Finally, we finished in the city of Siena, sipping aperol as the sun beat its way down onto the Piazza del Campo.
All in all, it made for an extremely memorable Tuscan road trip.
If I’ve piqued your interest, then you’ll need to read on. In this Tuscany travel guide, discover how best to structure your Tuscan road trip, uncover the best places to visit in Tuscany by car, figure out how many days you will need and uncover some of the best accommodation in the region.
By the end, you’ll be equipped with enough information to build an unforgettable Tuscany road trip itinerary.
Essential links for booking your Tuscany Road Trip
Table of Contents Show
Planning your Tuscan road trip – before you go
Do I need a car in Tuscany?
While it is possible to discover much of Tuscany without a car (logistics would incorporate a range of trains, local buses and possibly guided tours), the most flexible way to travel around Tuscany is by car.
As this post is also about crafting a Tuscan road trip specifically, then I’m going to say yes – you will definitely need a car in Tuscany if you follow my proposed route!
I always use rentalcars.com when hiring a car abroad and our road trip to Tuscany was no different. I like them for the following reasons:
- You can compare all car rental companies in a given destination. They also have superior filtering options too, so you really can drill down to what you’re looking for – even to the deposit amount and payment type.
- All the info you need for your relevant booking can subsequently be found in their convenient app – no print outs necessary.
- You can often amend/cancel your booking with no additional charges.
Is driving in Tuscany difficult?
I would go so far in saying that no, driving in Tuscany was not particularly difficult and it definitely does not present the same challenges as driving in other parts of Italy (*ahem* Amalfi Coast and Rome!). I really do think that it is the best way to travel around Tuscany.
If you avoid driving in Florence and also avoid the central, historic areas of any other towns and cities visited (which are often ZTL zones, with restricted access anyway), then you should not have much trouble.
Roads in Tuscany are for the most part, quite good, with much of the transiting between major towns and cities done on Autostrade (highways) and regional roads.
Some of your Tuscany trip route will take you on narrower, windier, more provincial roads but again, these should not pose too much difficulty.
Check your route in advance of your departure and if you have a companion, have them look further along the map as you drive to let you know in advance of any tricky parts of the route. These roads are typically a lot quieter too so once you take your time, you’ll be absolutely fine!
When is the best time to visit Tuscany?
As I’ve already touched on briefly in this post, spring is an absolutely wonderful time to visit Tuscany. The months of April, May and June see the Tuscany countryside begin to blossom and its charming small towns come to life.
The month of April is the quietest in spring (with the exception of Easter time) – you will find accommodation rates will be a little cheaper and busy tourist attractions will also be a little less crowded, making it a choice time to visit.
You also, however, run the risk of some rain showers at this time of the year.
We travelled in April and were relatively unaffected by any rainfall, with rain occurring on two mornings only. Average temperatures in Tuscany in April range from highs of 66 °F (19 °C) to lows of 46 °F (8 °C) and I found conditions to be true to this range.
By June, these averages swing upwards substantially to daily highs of 81 °F (27 °C) and lows of 59 °F (15 °C). For those seeking more guarantee of sunshine and warm weather, June may be a better time to visit Tuscany.
Wine lovers, take note of May – on the last weekend of May each year, both large wine estates and small farms open up to the public for special visits and tasting as part of the Cantine Aperte activities.
July and August get increasingly hotter in temperature and are also peak tourist season, so it is a time where I would avoid travelling to Tuscany if you can.
The autumn months of September and October are also a wonderful time to travel to Tucany. Offering similar conditions to June and May respectively, where autumn differs to spring is in the change of colours and when the undulating pastures of the Val d’Orcia turn a burnt orange.
For foodies with an interest in truffle, chestnut and/or mushroom hunting, this is a great time to visit as these foods all come into season in autumn and foraging is a popular activity at this time.
Structuring your Tuscany road trip itinerary – creating an outline
Tuscany driving routes are plentiful and my head was in a spin for weeks when I started planning this trip, as I agonised over what to include and what to take out of our self driving tour of Tuscany.
Tuscany is a region that demands you to explore it slowly and for your Tuscany road trip, I would urge you to do it this way too.
Instead of trying to cram too much in, get lost in the labyrinth of winding streets in its hilltop towns, savour those sips of Chianti wine and gorge yourself on the hearty offerings of Tuscan cuisine. If you’re eager for more, consider indulging in Chianti wine tours from Siena.
I feel like our Tuscany itinerary had the perfect balance of relaxation and exploration, with 2 days (3 nights, with a late arrival on our first day) starting in Florence and a further 6 days exploring the Tuscan countryside and some of its towns and cities.
There are a number of Tuscany driving routes you can take, but with some prior planning you can structure it so that you can take a detour to some other towns when transferring between the places that you overnight in.
Our Tuscany road trip itinerary was as follows:
| Time spent | Area of Tuscany |
|---|---|
| 3 nights | Florence |
| 2 nights | Greve in Chianti |
| 2 nights | Montepulciano |
| 2 nights | Siena |
When travelling in between the above destinations, we also managed to fit in trips to Panzano, Lamole, Arezzo, Pienza and the famous Cappella della Madonna di Vitaleta.
Tuscany road trip map
To help you visualise our Tuscany route, I’ve created a map of our road trip itinerary below. You’ll see that we worked our way around Tuscany in a clockwise direction, concentrating on the areas of Chianti and the Val d’Orcia.
I broke it up so that there was never too much time spent driving and also stopped off in additional locations where it made sense to (and where it didn’t, no matter how much I wanted to visit, I didn’t include on our Tuscany itinerary.
If somewhere was too far out of the way or added stress or time constraints to our route, it was cut from the itinerary – I’m still pining after San Gimignano having sadly lost out this time round!).
Driving times and distances were as follows and all in all, you will see that there were no long journeys:
| Start/End Point | Distance | Time |
|---|---|---|
| Florence to Greve in Chianti | 28km / 17mi | 44 minutes |
| Greve in Chianti to Lamole | 9km / 5.6mi | 16 minutes |
| Greve in Chianti to Panzano | 8km / 5mi | 10 minutes |
| Greve in Chianti to Arezzo | 62km / 38.5mi | 1 hours 5 minutes |
| Arezzo to Montepulciano | 53km / 33mi | 49 minutes |
| Montepulciano to Pienza | 15km / 9mi | 21 minutes |
| Pienza to the Cappella della Madonna di Vitaleta | 6km / 3.7mi | 12 minutes |
| Cappella della Madonna di Vitaleta to Siena | 52km / 32.3mi | 1 hour |
| Siena to Florence | 73km / 45.3mi | 1 hour 5 minutes |
How many days do you need to visit Tuscany?
Considering we’re talking about a Tuscan road trip here, this type of trip lends itself more to the concept of slow travel and the idea of immersing yourself in a destination.
To have a true ‘road trip’ experience, you really want to allow for at least 5-7 days in the Tuscany countryside, with additional days to explore the city of Florence.
Any less and you take away from the experience and start rushing between destinations. If you have more time than this, then great – go for it!
I really wasn’t ready to go home when my 10 days in Tuscany were up, so take advantage of this extra time if you have it to uncover more of Italy’s best region! There is enough in Tuscany to keep you occupied for two weeks or more.
In the section below, I will both outline in more detail those locations we visited, along with those that I would have liked to have experienced had we had more time to spend in Tuscany.
I appreciate that you may not have the same amount of time in Tuscany as I did, so you can add and remove suggestions as you see fit and depending on what appeals to you most.
Road trip Tuscany – route in detail with suggested additional stops
As I’ve already mentioned, there are a number of Tuscany road trip routes that you could take.
While you could also explore the areas of the north of Tuscany around Pisa and Lucca and the coastal area of Maremma in the west, I decided to focus on two main regions within Tuscany (and arguably, its best known), namely; Chianti and the Val d’Orcia.
If you have a similar length of time to me in the Tuscan countryside (5-7 days), I suggest you adopt a similar approach. If you have longer to spend, consider adding an additional part of Tuscany to your Tuscany driving itinerary, but bear in mind that there were still parts of Chianti and the Val d’Orcia that I didn’t get to see.
So it all depends on whether you want a more immersive experience, or a whistle-stop tour!
Below are the stops that formed part of my Tuscan road trip, together with some additional suggestions in each area should you wish to spend more time there. Let’s begin!
Tuscan Road Trip Days 1 & 2: Florence
Nestled in the rolling hills of Tuscany is its capital city; Florence. Home to countless Renaissance masterpieces and some of the most important and famous collections of art in the world, this is a city that oozes culture and history through every fibre of its being.
In the 14th-16th centuries, the city of Florence flourished as a centre of thinking, commerce and the arts. Responsible for lighting the embers of the cultural revolution, or ‘Renaissance’, which blazed its way through Europe in the middle ages, much of this change was driven by the illustrious Medici family.
The Medicis rose from humble origins as wool merchants and money lenders to climb the ranks of Florentine nobility and eventually install themselves as rulers of Florence. Evidence of their influence is seen everywhere you go in Florence, from its galleries to the architecture of its buildings.
There is much to do and see in Florence and I have covered the topic extensively in my guide to Florence in 2 days (with enough in here to keep you going for longer than 2 days should you wish). Some particular highlights for me, however, were the following:
- The Uffizi Gallery
- The Statue of David and the Galleria dell’Accademia
- Climbing Giotto’s Campanile for views of the cupola of Florence’s Duomo
- The springtime wisteria and city views at the Bardini Gardens
- Walking through the streets of the Oltrarno in the early hours to Piazzale Michelangelo
- Dinner al fresco at 4 Leoni in the Oltrarno
Where to stay in Florence
We stayed at White Irish Florence Apartment while in Florence, a beautiful boutique apartment at the top of an old building that backed onto the Piazza della Signoria.
This was perfect for our needs, as we spent most of our time exploring the streets and restaurants of Florence so didn’t require accommodation with any services, but wanted somewhere that was centrally located, clean, comfortable and aesthetically pleasing. This definitely fit the bill!
Related post: Ultimate List Of The Best 17 Airbnbs In Florence Italy For Luxury Lovers
If you would prefer to stay at a hotel, a fantastic boutique option in Florence is AdAstra Suites, a quirky lodging that occupies the upper floor of a beautiful, historic palace in the Oltrarno with gorgeous views over large, private gardens.
Those looking for a luxury option should consider the Hotel Lungarno.
Set on the banks of the Arno river, this luxurious hotel which is owned by the Ferragamo family is situated 100m from the Ponte Vecchio and offers wonderful views of Florence’s famous bridge. It also boasts a Michelin-starred restaurant onsite.
Top Tip!
Don’t pick up your car rental until you’re finished in Florence. You won’t drive while in the city and will have to deal with the conundrum of having to find and pay for parking if you do.
Tuscan Road Trip Days 3 – 5: Relaxing in the Chianti region
We picked up our rental car at Florence airport and then made our way through the rolling hills of Tuscany, climbing upwards until we reached Greve in Chianti.
Our final stop was not quite the town, however, but the glorious Renaissance villa of Vignamaggio, birthplace of one of the most famous ladies in the world, the Mona Lisa, and the movie setting of Kenneth Branagh’s ‘Much Ado About Nothing’.
Here was a place that was perfect to do, well, nothing! After a busy couple of days spent delving into the delights of Florence, we were keen to switch off and enjoy the scenery and wine of the Chianti region.
We spent our two days in Chianti ambling through the vineyards at Vignamaggio, reading books, drinking Chianti Classico and eating at the great farm-to-table restaurant onsite.
We also ventured into the nearby hilltop village of Lamole (which – warning – is a bit of a white knuckle drive in parts!) and enjoyed a wonderful evening meal with fabulous hosts at local restaurant, Ristoro di Lamole.
This restaurant is very highly regarded and well worth a drive to dine at, offering sweeping views of the Chianti hills below. Don’t make the same mistake we did and turn up without booking – we couldn’t be accommodated at lunch, but thankfully, managed to squeeze in for an evening sitting.
Our second and only other outing was to the nearby Panzano in Chianti, to head to the stable of Italy’s most famous butcher, Dario Cecchini, to try out his restaurant.
Offering two fixed menus at two separate restaurants located across the road from each other (tip – go to Solociccia), all dishes centre around beef and I never realised until then that beef could come served in so many different ways (including a dish that was rather unfortunately translated to English as ‘rosemary up the bum’!).
Where to go in Chianti if you have more time
The Chianti region is littered with numerous and atmospheric medieval towns and hamlets. We had a very relaxed time while in Chianti and some additional places that I would have loved to visit while we were there are the following:
- San Gimignano – a fortified medieval town with city walls dating back 1,000 years. A UNESCO World Heritage Site, this town is famous for its towers and unique skyline.
- Volterra – formerly an important Etruscan town, Volterra also passed throught the hands of the Medici. Numerous points of interest, including an Etruscan museum, the ruins of a Roman Theatre and the Pinacotecta, a gallery that features the works of great Tuscan artists.
- Castellina in Chianti – an ancient town that dates back to the Etruscans, complete with imposing castle, underground roads and jaw dropping views.
- Rada in Chianti – a medieval town, again offering fantastic views of the surrounding vineyards.
- Castelnuovo Berardenga – a beautiful red brick town with a bell tower located in the southernmost part of the Chianti Classico area.
Where to stay in the Chianti region
Here is an area in which I’d encourage you to have that Tuscan villa experience and use this as a base to explore the surrounding countryside. Personally, I loved our time spent at Vignamaggio and would happily return.
For such a grand location, it still had a very rustic feel that was totally unpretentious and there were 500 acres of estate to explore too.
An alternative worth considering is Il Borgo di Vescine, which offers something different to Vignamaggio in that it is a 13th century village, now turned country resort.
It is located in Chianti Classico’s Gallo Nero area, which is prolific for its wine production. Its rooms are set within the original houses of this medieval hamlet.
The exquisite Castello di Spaltenna is located near Gaiole in Chianti, in an ancient monastery dating from the 10th century. Complete with beautiful views, a spa and a Michelin-starred restaurant, it is a great option for those with a larger budget.
Finally, jewel in the crown of Chianti villas is, for me, the luxury country estate of Borgo Pignano. Situated in the hills of Volterra on no fewer than 75 hectares, this is the ultimate luxury retreat in Chianti and has been placed firmly on my wishlist for when I return.
// Transfer to Val d’Orcia via Arezzo
The next stage of our journey took us to the Val d’Orcia region of Tuscany and along the way we stopped off at the small city Arezzo. I was very pleasantly surprised by Arezzo.
You approach through its more modern fringes, but at its heart is a gloriously medieval centro storico, perched atop the rest of the city on one side, and on the other, sweeping views of the fields of Tuscany below it.
We primarily visited Arezzo as I wanted to see the Legend of the True Cross fresco (an early Renaissance masterpiece by Piero della Francesca), but we uncovered a whole lot more during our day trip.
Top things to do in Arezzo that you should endeavour to see, even if stopping briefly include:
- The Basilica of San Francesco and the Legend of the True Cross Fresco – 100% worth a detour to see.
- The Fortezza Medicia, an imposing Medici fortress that offers some tremendous views.
- Casa del Vasari, or in English, Vasari’s house. Vasari was an artist and was also the man responsible for designing the Vasari Corridor on the Ponte Vecchio and the Uffizi in Florence. He decorated his house in Arezzo with hand painted frescoes and it is truly a joy to behold.
- The Piazza Grande, Arezzo’s sloping main square and the beautiful vaulted arches of the Loggia Vasari.
If you fancy overnighting, a place to stay in Arezzo that I would book myself without hesitating would be Sweet Tuscany Cavour, a beautiful, old apartment in the centre of Arezzo complete with a four poster bed and frescoed ceiling.
Tuscan Road Trip Days 6 & 7: The Val d’Orcia and Montepulciano
Next up on our tour of Tuscany was what is arguably the most scenic part of Tuscany; the Val d’Orcia.
As we travelled onward from Arezzo the landscape began to change – the hills became more undulating, cypress avenues began popping into view and soon we entered quintessential Tuscany; the one that looks like a painting in photographs.
Having now visited in real life, I can confirm that it not only looks like a painting, but it actually feels like you’re in a painting too.
Touring through the Val d’Orcia is amongst the best drives in Tuscany and indeed, the entire country of Italy too. Take the SR2 to find Poggio Covili, that famous farmhouse with a cypress tree lined avenue which has been immortalised as one of Tuscany’s most famous photo locations.
Drive the SP146 to encounter Podere Belvedere, made famous as it played a starring role in the blockbuster movie Gladiator.
Another photogenic house along this road is Genna Borborini Maria Eva (but please do respect that this is private property if you do stop for a snap). The famous Capella di Vitaleta is also along this road (more on that below).
We based ourselves just outside the Renaissance hilltop town of Montepulciano, a place that I am aching to return to. We arrived in town just as the sun was setting over the Val d’Orcia, in what was one of the most special sunsets I’ve witnessed to this day.
Montepulciano is an extremely unique, well-preserved spot and I’d love to hear all the stories that its ancient walls could tell. Famous for its very special wine, Vino Nobile di Montepulciano, it’s a great part of Tuscany in which to do a winery tour.
Our villa organised a tour for us at a local, biodynamic winery which was one of the more memorable parts of our trip to Tuscany.
Check out some Montepulciano wine tours here.
Day trip to Pienza & Capella di Vitaleta when transferring to Siena
Pienza
Pienza makes a wonderful day trip from Montepulciano and it is also very easy to visit if you are transiting from Montepulciano to Siena. In the 15th century, Pienza (then known as Corsignano), struck gold when a citizen from this formerly humble village was elected Pope Pius II.
He set about making Pienza the ideal Renaissance town, enlisting the help of famous architect Leon Battista Alberti to remodel the town based on humanist urban planning principles. Upon Pius’ death, the redevelopment halted and what remains today has been virtually untouched since that time.
A UNESCO World Heritage town, Pienza is also famous as the capital of pecorino cheese and together with its astounding views of the surrounding fields and cypress trees of the Val d’Orcia, it is an extremely compelling day trip proposition on your road trip to Tuscany.
Capella di Vitaleta
Close to Pienza is one of Tuscany’s most recognisable photo locations – the Capella di Vitaleta, or to give it its full title – the Capella della Madonna di Vitaleta.
This beautiful chapel was built on the site of an apparent apparition of the Virgin Mary to a shepherdess and in 1553, a statue of the Virgin Mary was installed in the chapel. This was later moved to the nearby San Quirico and the church was remodelled in the 1800’s.
Many shots you will see of the front of the chapel, surrounded by the hills, have been taken with telescopic lenses from the roadside of the SP146 from this viewing point.
However, if you’re like me and aren’t content until you see the chapel up close and personal, then make your way instead to the carpark (ie the side of a muddy road where you can leave your car – coordinates here) and wander through the fields to reach the chapel.
I immensely enjoyed this adventure, as on the way to the chapel you are enveloped by the silken pastures of the lolling Tuscan hillsides and to watch the light flicker and dance its way across these is truly a sight to behold.
Where to go in the Val d’Orcia if you have more time
As a wine drinker and a big fan of Tuscan reds, I would have loved nothing more than to spend an additional couple of days around Montalcino, which is famous for its production of the prestigious wine, Brunello di Montalcino, in order to visit a winery or two and to see more of the surrounding Tuscan countryside.
Close to Montalcino, too, is Sant’Antimo Abbey. This is a beautiful and ancient Benedictine abbey nestled amongst the Tuscan hills that is famed for its Romanesque architecture.
This fantastic all-day Brunello di Montalcino wine tour runs from Siena and includes a visit to Brunello di Montalino wine cellars, three wineries, a traditional Tuscan lunch and stop offs at the town of Montalcino and the mystical abbey of Sant’Antimo – it would make a memorable addition to your trip.
Another thing that Tuscany is known for are its natural hot springs. Instagram has thrust Saturnia Hot Springs (or Terme di Saturnia in Italian) into the limelight but these are 1 hour 45 minutes south of Montepulciano in the Maremma region and 1 hour 20 minutes from Montalcino.
So I’d include these in your Tuscany road trip itinerary only if its a bucket list item for you, or if Maremma is in your plans.
An alternative to the Saturnia Hot Springs are the hot springs at Bagni San Filippo, which are a 45 minute drive from Montepulciano and a little longer if visiting from Montalcino.
RELATED READING | Best 15 Brunello Wine Tours: Curated Picks & Essential Tips
Where to stay in the Val d’Orcia
In terms of where to stay, you can’t go wrong with the areas surrounding either Montepulciano or Montalcino when choosing a base in the Val d’Orcia.
Where to stay in Montepulciano
For the Val d’Orcia section of our road trip in Tuscany, we chose the refined Villa Poggiano, which is located a couple of kilometres outside the walls of Montepulciano.
It’s an extremely elegant property, complete with an ornate, outdoor swimming pool on a private estate that offers beautiful views of the Tuscan countryside.
An alternative that I considered when booking the above was Lupaia – this offers what I would call a luxe farmhouse experience in the countryside of Tuscany.
Its reviews are close to flawless and the only thing that made me choose Villa Poggiano over Lupaia at the time was that I wanted a villa experience over a farmhouse one for our time in Montepulciano. Check it out though, as it’s an absolute stunner.
Finally, for those who would prefer to be within the walls of Montepulciano itself, then Palazzo Nobile di San Donato is the one for you. A designated Residenza d’Epoca (a period building of historical significance), these luxurious suites are decorated with gorgeous antique furniture, Tuscan tiles, wooden beams and frescoes.
They offer incredible views of the Piazze Grande and the Val d’Orcia from their windows.
Where to stay in Montalcino
If your pockets are on the deeper side, then how does a 10th century castle on the top of a hill complete with a spa and thermal pool sound to you?
If it sounds like your cup of tea, then take a look at Castello di Velona, which is a five star, Leading Hotels of the World property located in the countryside close to Sant’Antimo Abbey.
If a luxurious farmhouse is more your thing, then Casanova di Neri Relais is a wonderful option. The setting of this gorgeous farm stay has to be seen to be believed.
With a large outdoor pool (and an indoor one too), its interiors are also a dream with traditional features such as Tuscan tiles, bleached wooden beams and exposed brickwork, sympathetically tied together with contemporary, luxe touches.
Another, more affordable boutique bolthole close to Montalcino is Dimora dell Muse. Along similar lines to the above, its rooms are equally as gorgeous but it does not come with the pool that Casanova di Neri Relais offers. Still a fabulous choice, however.
Tuscan Road Trip Days 8 & 9: Siena
The medieval stalwart of Siena sits across three of Tuscany’s hills. At its heart is the magnificent Piazza del Campo, famous worldwide as the site for the yearly Palio race, when Siena’s main square is transformed into the scene of a scintillating horse race.
Towering above the piazza is the Palazzo Publico and its tower, the Torre del Mangia.
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While Florence is famous for its dome, Siena is known too for its magnificent gothic cathedral. Upon entering, your gaze is immediately drawn upwards (and your jaw towards the floor) to take in its striking white and green marble columns and frescoed ceilings.
Filled too with works of art by Renaissance masters, the Duomo of Siena should be your first port of call when visiting Siena.
To walk the streets of Siena is to walk back in time, with much of its centre perfectly preserved from its days of power during medieval times. Compared to Florence, there is definitely a more rustic feel but that is not to say that Florence’s country-cousin is any less appealing.
Things to do in Siena that you should consider include:
- Visiting the spectacular Siena Cathedral – yes, it is worth paying the admission and yes, it’s worth queuing for if you need to buy a ticket (or you can book yours in advance, together with a walking tour of Siena here).
- Soak in the atmosphere of the Piazza del Campo. If you’re feeling energetic, climb the 400 steps of the Torre del Mangia for birds eye views of Siena.
- Visit the Pinacoteca Nazionale, a gallery that is full to the brim of gothic masterpieces.
- Get lost in the streets of Siena – they are made for wandering and each corner you round presents a new delight.
- Enjoy Sienese cuisine in an Etruscan cavern. There are a number of these underneath the city of Siena and many of these have been repurposed into wine cellars and restaurants, amongst other things. Antica Osteria da Divo is one that I can highly recommend.
Where to stay in Siena
Unfortunately, I cannot recommend our accommodation in Siena – the rooms were very tired and much in need of a facelift.
I had been particularly taken with Il Battistero Siena Residenza d’Epoca during my search for the best place to stay in Siena but alas, it was booked out – which is always a good sign! This historical building overlooks Siena Cathedral and has also received rave reviews from previous guests.
If you’re looking for another Residenza d’Epoca option in Siena, then Palazzo Borghesi, former home to the famous Borghesi dynasty is an absolutely stunning alternative.
Those in search of a luxurious, 5 star hotel in Siena will be suitably apeased by the magnificent Grand Hotel Continental Siena. This opulent hotel is dripping with frescoes, valuable artwork and marble and is located in the historical part of Siena.
If you’d prefer to base yourself on the outskirts of Siena for easier access to the Tuscan countryside, then I have a lovely option for you. Four star Hotel Certosa Di Maggiano is located 2km from Siena’s Piazza del Campo in a 13th century former monastery.
Its beautiful cloisters run alongside a heated outdoor swimming pool and the property is surrounded by olive groves and vineyards.
Other areas to consider for your Tuscan road trip
When crafting the above Tuscany road trip route, I purposefully focused on the areas of Chianti, the Val d’Orcia and Siena so that we could have a more immersive experience of those areas.
If you get itchy feet when traveling and the urge to explore as many towns in Tuscany as you can (or, plain and simple, you just have more time), then there are more fantastic areas of Tuscany that you can explore.
Maremma
One is always quick to associate Tuscany with its countryside and inland towns, but there is also a coastal area of Tuscany too, Maremma, which incorporates the regions of Grosetto and parts of Livorno. If you’re seeking to add some sun, sea and sand to your Tuscany road trip, then Maremma is your answer.
The region is also known for its Tufa towns of Pitigliano, Sorano and Sovana. These hilltop towns are carved out of the rock and play an important role in the Etruscan history of the region, encompassing an important archaeological area in Tuscany.
Northeastern Tuscany
You may have been waiting for my itinerary to include Pisa, but alas – we decided that it was simply too much for us to cram in. Pisa is famous for – you got it – its Leaning Tower of Pisa!
There are also many thermal hot springs in the area too, but what would draw me to Northeastern Tuscany in particular is the medieval town of Lucca, where you can walk or bike the almost 4km length of walls that circumnavigate the town.
The beautiful town of Pistoia sits at the foot of the Apennine Mountains and is another destination to explore when in the north of Tuscany.
Onwards from Tuscany for a road trip of Italy
A visit to Tuscany may only be forming part of an Italy road trip for some readers, so below are some other areas of Italy that link up with a trip to Tuscany particularly well:
| Area in Italy (area in Tuscany) | Driving distance |
|---|---|
| Rome (from Montepulciano) | 180km / 112 mi |
| San Marino (from Arezzo) | 132km / 82mi |
| Bologna (from Florence) | 104km / 65mi |
| Cinque Terre (from Pisa) | 113km / 70 mi |
And of course, the same journeys would apply in reverse if making your way to Tuscany from any of the above!
To finish – some tips for driving in Tuscany
To wrap things up, let me leave you with a few Tuscany driving tips to help your journey go as smoothly as possible:
Get a small car
Only go as large in car size as you need to for driving in Tuscany. The older parts of small Tuscan towns have very narrow streets, so you don’t want something that you’re worried about scraping against other cars, walls, immovable objects etc!
I don’t know if it’s just me either, but usually a smaller car is worth less in value too and that makes me a little less nervous about driving it.
Avoid ZTL zones
I’ve mentioned these in brief above, but these are restricted traffic zones in the historic centre of towns, created to minimise traffic in these areas (and which I think are a good idea).
The giveaway here is a sign marked “ZTL”, but these are often easy to miss, so check in advance of any places you are traveling to find out where the ZTL zone starts.
While some traffic is permitted to enter these areas, they have special dispensation to do so, and if you enter without same then you could incur some hefty fines. If you need to access/park at accommodation that is in a ZTL zone, liaise with your accommodation in advance to organise the necessary permissions.
Ensure you have a Google Maps or a GPS in the car
Might seem obvious, but make sure you know where you’re going. If you’re travelling as an EU citizen then you will likely have data roaming via your home mobile network.
However, network signal can sometimes be patchy in remote areas (and mine often has a tendency to drop completely when abroad), so make sure to download your Google Map for offline use and have searched and loaded the route when you have WiFi or mobile data.
If you are traveling from a country outside of the EU, then either purchase a local SIM card, or just pay the extra few Euro for the peace of mind a GPS will give you for navigating your way around Tuscany.
Watch the speed limit!
I say this, but that’s not always entirely easy to do. There are many electronic cameras along roads in Tuscany to try and catch those speeding. These are often preempted by a sign that warns of said camera, but you won’t quite know where they are placed.
Speed limits can also vary greatly along roads, so watch that you don’t miss one that indicates a change of speed limit and thus incur a fine for speeding.
If you’re thinking that you may escape paying these as you’re driving a rental car in Tuscany, then don’t get too excited – they’ll pass it to your car rental company, who then charge you an administrative fee for handling it too.
These tickets often take months by the time they come through to you too, so just save yourself and the worry and focus less on burning rubber and more about following speed limit signage when driving around Tuscany!
Bring a USB charger with youThis is the one thing that I would not be without on any road trip and it’s saved my bacon many a time.
Snapping pictures and especially utilising Google Maps is a serious drain on your phone battery, so pack a USB charger that you can use in the car. The same goes for camera chargers, GoPro chargers etc.
Related reading for Tuscany
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