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Road trip through Tuscany: The most beautiful stops and our tips

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Hello Tuscany! Hello place of longing! We make no secret of it – between Tuscany and us it was love at first sight. Tuscany combines Italian lifestyle and holiday flair in a wonderful way. Our last road trip through Tuscany was one of our best vacations ever.

We have already been to Tuscany twice. This article is, so to speak, a best of these two road trips. We will show you which places in Tuscany we can particularly recommend. Of course, as always, there are our personal tips. You can also find all the stops on our road trip marked on a map at the end of the article.

1. Tuscany: What you can look forward to Olive groves and vineyards as far as the eye can see, rolling hills, picturesque towns: Tuscany is on some places really too good to be true. So you can look forward to lots of postcard motifs.

In Tuscany there are some beautiful, romantic towns, including, of course, the capital Florence with its imposing cathedral. But we also like the smaller towns. We were particularly enthusiastic about Lucca – a charming small town with a well-preserved medieval city wall.

But Tuscany wouldn’t be Tuscany without its characteristic landscape features: The gentle, hilly landscape of Tuscany is beautiful to look at. And not to forget, of course, the distinctive cypress alleys and olive groves.

Buy breakfast at the Italian grocer in the morning and enjoy the sunset in the countryside in the evening – more Tuscany -Feeling doesn’t work at all! We promise you: In Tuscany it will be easy for you to switch off. The clocks tick slower here.

2. Itinerary through Tuscany: The stops of our road trip Florence Florence is the ideal starting point for a road trip through Tuscany. And there is a reason for that: Florence is the capital of Tuscany and is therefore home to one of the largest airports in the region.

With almost 400.000 Florence is not a city of millions of inhabitants, but it is larger than expected. And: Pretty touristy – at least in the center. Nowhere else in Tuscany was coffee more expensive than in Florence.

The most famous sights in Florence are the Uffizi Gallery – a building complex, which today is one of the most famous art museums in the world. The best thing to do here is to get tickets in advance. A highlight is the imposing cathedral of Florence called Santa Maria del Fiore. Your sight is simply overwhelming. For us, the cathedral is one of the most beautiful we have ever seen.

Our tip: Don’t miss the sunset over Florence from the Piazzale di Michelangelo. This is anything but an insider tip, but the view over Florence from up here is simply fantastic.

Detailed blog article: Florence Travel Guide

Our hotel tip for Florence: Corte Calzaiuoli Elegant Suites

Beautiful, very stylish, small boutique hotel right in the historic center. Definitely one of the most beautiful accommodations on our road trip.

Lucca Of all the cities in Tuscany, we were particularly fond of Lucca and therefore believe that Lucca should not be missed on any Tuscany road trip should be missing. The architecture is medieval : Lucca, for example, is surrounded by an excellently preserved city wall . On this 4 km long wall you can walk or cycle around Lucca.

One of the most famous sights in Lucca is the Piazza dell’Anfiteatro. As the name suggests, this course was built on the ruins of a Roman amphitheater and therefore has its characteristic oval shape.

Our tip: You should not miss the view from Torre Guinigi (Guinigi Tower). From up here you have a wonderful panoramic view over Lucca.

Related article: Lucca Tips

Our hotel tip for Lucca: Il Pozzo di Santa Zita

Very nice boutique hotel in a historic house with individually furnished rooms. The location in the center of Lucca is also great.

Pisa Welcome to the city that houses the most famous sight in Tuscany: the Leaning Tower of Pisa. The Leaning Tower of Pisa is one of the symbols of Italy. So it’s no wonder that the rush is even greater than we had expected.

Of course it’s great to see the tower with your own eyes to see, but we admit: there are definitely more impressive and charming places than the green areas of the Piazza dei Miracoli around the Leaning Tower of Pisa. In midsummer, the visit becomes a gauntlet run by tour groups.

The Cathedral of Pisa is right next to the Leaning Tower of Pisa (Cathedral of Santa Maria Assunta). All in all, the center of Pisa impressed us less than that of Lucca.

Our hotel tip for Pisa: B&B Di Camilla

Very tasteful accommodation in country style. The location is central, but still quiet.

Volterra As soon as you arrive, Volterra is impressive: the medieval town is enthroned on a hill, visible from afar. The alley labyrinth of Volterra would have the potential to be one of our favorite places in Tuscany if Volterra weren’t so incredibly well frequented.

Nevertheless, Volterra is definitely worth a stop. Volterra is also called Alabaster City: the city is known for the mining and processing of alabaster. That’s why you’ll find countless shops in the center that sell products made of alabaster. Most of them are classic souvenir shops.

Our accommodation tip: Villa Loghino

Very stylish accommodation in an old country house with pool. Located outside the center of Volterra but very quiet.

San Gimignano San Gimignano is one of the most suggestive towns in Tuscany and also known as “Medieval Manhattan” known. As you approach San Gimignano you will know why: Overall 15 towering medieval towers up and give the city its unmistakable appearance.

A highlight is the view from one of the towers over San Gimignano. The best known is the view from Torre Grosso. Although you can read everywhere on the internet that this is the only tower that can be climbed, we were on another tower ourselves. In our case, it was a tower that houses an apartment and can probably only be visited when the apartment is not rented. Either way: You shouldn’t miss San Gimignano from above.

Our tip: This is very close to San Gimignano Weingut Teruzzi&Puthod, where we also stopped by. If you want to buy a bottle or two of wine, you’ve come to the right place. One of the classics of this winery is the Tuscan white wine Vernaccia di San Gimignano.

Detailed blog article: San Gimignano Tips

Our hotel tip for San Gimignano: Podere Sant’Elena

Very nice accommodation in a restored country house with Pool and large garden. A bit outside of San Gimignano, but in a very idyllic location.

Bolgheri For two things is the small charming place particularly well known: On the one hand you will find a lot of wineries in and around Bolgheri. And on the other hand the journey to Bolgheri is very special: the famous cypress alley, the so-called Viale dei Cipressi, along. Centuries-old cypresses line this road.

Bolgheri itself is a charming little town that is fairly easy to explore. Worth seeing is the Bolgheri Castle, through whose gate you drive when you come to Bolgheri. Otherwise you can pass the time in one of the wine bars – there are quite a few in Bolgheri.

Siena Siena, im Located in the heart of Tuscany, it is considered one of the most beautiful and most attractive cities in Italy. It is not for nothing that the old town of Siena is a UNESCO World Heritage Site. We were simply blown away by Siena!

The best place to start your city tour is at the most important square in Siena, the Piazza del Campo. This spacious, shell-shaped square is open at any time of the day It is a popular meeting place for locals and tourists.

You have a magnificent view over Siena from the tower of the Palazzo Pubblico, the Torre del Mangia . More than 400 There are steps to conquer before you can enjoy the panoramic view over Siena. It’s really breathtaking!

Further blog article: Siena Tips

Hotel -Tip for Siena: Casatorre dei Leoni

Beautiful, very tasteful accommodation in a historic house in the center. We felt incredibly comfortable here.

Val d’Orcia One of the most iconic destinations on our Tuscany road trip is the wonderful Val d’Orcia, located south of Siena. Here all the Tuscany clichés that buzz around in your head become reality.

Here you can look forward to beautiful, medieval towns surrounded by a picturesque, gently rolling landscape. We particularly liked it in Pienza, Montalcino and Montepulciano.

For wine lovers, the Val d’Orcia is also a must on a holiday in Tuscany. This is where the vines of the top wine Brunello di Montalcino grow.

Detailed blog article: Val d’Orcia Travel Guide

Our accommodation tip: Borgo Canalicchio Di Sopra Relais

A wonderful hotel in a quiet location surrounded by vineyards and olive groves. This is how you imagine the perfect vacation in Tuscany!

3. Map: All destinations of our Tuscany road trip at a glance So that you can better imagine where the individual places of our Tuscany road trip are road trips are located exactly, we have marked the stops on this map for you.

4. More travel tips for your Tuscany road trip Transportation in Tuscany : Tips for booking a rental car If you are not traveling to Tuscany with your own car, then we can only warmly recommend you to book a rental car. Many places in Tuscany can only be reached with difficulty by bus. With your own car you are much more flexible – and in our opinion you need this flexibility for a trip through Tuscany.

We always book our rental car through Sunny Cars. Sunny Cars is an intermediary. That means: On the Sunny Cars website you get an overview of the cheapest rental car offers from various companies such as Hertz or Europcar.

The big advantage of Sunny Cars: You are Fully comprehensive insurance and in the event of damage, the deductible will also be reimbursed to you. Incidentally, an SUV is not necessary for Tuscany. We would bet on a mid-size car.

What is the best time of year for a road trip through Tuscany? Spring and Autumn are ideal for a trip to Tuscany. We particularly recommend May and June as well as September and October. The climate during these months is usually pleasantly warm, although it is not yet too hot. Also, not as many travelers are out and about as in the summer months.

On our last trip to Tuscany we were out in mid October and found this month easy only optimal. We would choose it again at any time.

If possible, you should avoid the midsummer (especially the months of July and August). We ourselves were once in August and can confirm that some places in Tuscany are hopelessly overcrowded during this period. This is especially true for the centers of historic cities such as San Gimignano and Volterra. If you want to combine your Tuscany trip with a beach holiday, then summer is of course preferable.

How much time should I plan for a road trip through Tuscany? Difficult question as this is very individual. On our first trip we were a week in Tuscany, but we could have easily found destinations for another week. Last time it was round 10 days – that was more to our liking .

If you prefer to take it slower, then we would recommend you plan about two weeks on site. This gives you enough time to explore a few places off the beaten track.

The distances should not be underestimated, because Tuscany is quite expansive: There are nine provinces and to cross Tuscany by car you need several hours. Even if Tuscany doesn’t look too big on the map, you have to keep in mind that some of the roads are not perfectly developed. Often you curve around on the country roads longer than you would have thought in advance.

Where to start from or where to stay ? There are basically two possibilities: Either you look for a home base and make of day trips there. Or you stay overnight in several places. We have already done both and can therefore say: both have their advantages and disadvantages.

1) Homebase: Central locations are ideal starting points in Tuscany: eg in the province of Pisa or Siena. We ourselves once stayed with our entire family at a historic country estate called La Lepraia in the province of Livorno. This had the advantage that we were not far from the sea. Our tip: Before you book your accommodation, use Google Maps to check the distances to the places you want to visit. Not that there are any nasty surprises.

2) Multiple locations: If you want to stay in multiple locations on your road trip, then you are a little more flexible. We chose this on our last trip to Tuscany. Of course you have to consider that this type of trip is usually less relaxing because you have to pack and unpack your suitcase all the time. If you don’t have your own car, Florence is a good starting point as many international flights land here.

33396Transparency: Affiliate Links This blog article contains our personal recommendations in the form of so-called affiliate links. If you book or buy something through the links, we will receive a small commission. For you, this does not change the price at all. A thousand thanks from both of us!

Have you ever done a road trip through Tuscany? Do you have any other tips? We look forward to hearing about your experiences!