Tuscany road trip: with your own or a rented car, where to stay in Tuscany, what to see in the Val d’Orcia valley and small towns.
I adore Italy — this country has long lived in my heart. And Tuscany was one of those places I had dreamed about for half my life. Dreams come true if you’re not afraid of long distances and carefully plan your trip.
Tuscany Road Trip
We chose a slightly unusual route, which will appeal to those who don’t like crowds and lots of people. That’s why we didn’t go to Florence and didn’t plan a visit to the Leaning Tower of Pisa. On the contrary, we added small towns to our route—Arcidosso, Pitigliano, Sovana, and also the coast of Grosseto. We wanted to immerse ourselves in rural Tuscany, see its tiny ancient towns, live with local farmers and restaurateurs amidst nature, enjoying wonderful Tuscan cuisine. So our route was as follows:
The ancient Siena, the endless hills of the Val d’Orcia preserve, small hilltop towns like Montalcino, Montepulciano, Pienza, tuff towns Pitigliano, Sovana, and Sorano, the beaches of Grosseto.
Features of a Road Trip in Italy
The best way to travel around Tuscany is to rent a car and enjoy the scenery, driving through winding roads curled between hills with vineyards and olive groves.
To rent a car in Italy, you need the following documents:
- Driver’s license—preferably of the new type, a plastic European sample with a limited validity period (10 years)
- Personal credit card—with a credit limit sufficient to pay for the rental and a temporary deposit for the rental car (300-1000 Euros depending on country and season).
- Driver’s international passport—for signing the rental agreement with the rental agency.
Toll roads and traffic rules in Italy
It seems to me that they are very expensive. Payment is at the barriers at the exit from the autobahn. At the entrance, you need to press a button and take a ticket. We entered the toll roads near Trieste and exited past Florence towards Siena. That’s over 500 km—it cost about 60 Euros.
Of course, there are also free ones—you can drive through villages, sticking to the speed limit (50 km per hour). But you lose a lot of time this way. So it’s up to you to decide: money or time, meaning free roads—slowly, or toll roads, but quickly.
A few more useful tips:
- Try not to refuel on Italian autobahns — the fuel price here is the highest. It’s better to do it on regular non-highway roads, at gas stations near towns and villages.
- There are many self-service gas stations in Italy. This means you need a credit card, from which a deposit (100 Euros) is initially taken, and after you refuel, the balance is returned minus the cost of fuel. By the way, prices at these stations are often cheaper than at those with a cashier.
- Do not exceed the speed limit—cameras catch everything and fines are high. The maximum allowed excess is no more than 5% over the allowed speed.
Recommended reading: How to rent a car in Italy – personal experience
What to See in Tuscany
We drove this route in 4 days, stayed in private apartments and agriturismo. We enjoyed Italian dolce vita: wine, cheese, Italian sausages, and prosciutto; in the mornings we drank coffee in small bars and cafes. We celebrated life and its flavors together with Italians.
Siena – the city of red stone
You absolutely must visit Siena—a medieval city made of red brick, very warm, cozy, and intimate. Stroll down its brick streets, step inside the Sienese Cathedral (Duomo)—a cathedral with a huge dome and striped black-and-white columns.
Be sure to visit the unique Piazza del Campo, which has a specific shape and its own features. The square slopes down towards the center by almost 5 meters, creating an amphitheater that is still used for performances today.
From the square, 11 main streets of Siena radiate like rays. They cut the city like a pie into 11 sectors. Visually, this is also very noticeable thanks to stones of different masonry and shades.
If you’re lucky, you can see the traditional horse race—the annual Palio, held around the square perimeter twice a year—on July 2 and August 16. On these days, the square turns into a racetrack with horses and jockeys galloping around it.
Where to stay in Siena:
- Casa di Alfredo Affittacamere has a wonderful view of the Tuscan hills, is located near the train station, and the price is very pleasant for a tourist city.
- B&B Dei Rossi with double rooms at 80 Euros, has excellent location—in the very center of Siena.
- Albergo Bernini≫ – Convenient location in the city center. The hotel is in an antique building, but it’s clean, has modern beds, and very attentive staff. Rooms have terraces where it’s nice to have coffee; there’s also a kettle and cups in the rooms for coffee and tea. At the same time, the accommodation price is very reasonable.
I recommend to read: 15 the most beautiful places in Tuscany
Val d’Orcia Valley
Val d’Orcia Valley—this is the rural heart of Tuscany. Here they produce the tastiest red wine, cheese, olive oil, which wins world prizes at various competitions each year. The landscape is stunning—almost every hill has either a town with its own fortress and tower, or an agriturismo or villa perched atop.
Fields, vineyards, and rows of olive trees stretch for 360 degrees. Villas are reached by winding paths, lined with ancient cypress trees. Each hill, sown with wheat or rapeseed, comes alive at the slightest breath of wind. It seems as if this blessed land breathes, soaking up the Tuscan sun and mists.
Mount Amiata rises above the valley (Amiata)—in winter, there is even a ski resort here. It’s hard to believe that a place like this gets snow.
If you love photography, here’s a list of shooting points:
- Riserva naturale Lucciola Bella
- San Quirico d’Orcia (SI)
- Cipressi di San Quirico d’Orcia
- Podere Belvedere
- Croce di Prata
- Punto panoramico Val d’Orcia
Type these names into Google Maps and add them to your itinerary—you won’t regret it!
Where to stay in Val d’Orcia:
- Relais Il Chiostro Di Pienza≫ – incredibly beautiful location in Pienza, rooms with a wonderful view of the Val d’Orcia valley.
- Hotel Palazzuolo≫ – Great location in San Quirico d’Orcia, the hotel has a wonderful view from the terrace and its own pool.
- Adler Spa Resort Thermae≫ – a beautiful resort in Bagno Vignoni, which is perfect for a wellness stay. The hotel has a gym and fitness center, thermal pools and several saunas on site.
- Drogheria e Locanda Franci≫ – the hotel is located opposite the castle in Montalcino. It’s linked to a wine shop and a restaurant nearby. This makes everything convenient for your stay.
Recommended reading: Val d’Orcia valley – why go to Tuscany’s most beautiful place
Montalcino
Montalcino—a town with beautiful views that you can see from the fortress walls. This is where Italy’s priciest wine is produced—Brunello di Montalcino. Take a walk through the old streets, stop by Piazza del Popolo to feel the medieval spirit. After your walk, step into any trattoria or cantina—a cellar for storing, tasting, and selling wine.
Order a glass of wine, a plate of cheese and meats to enhance your impression of the city with a vibrant bouquet of traditional flavors.
Where to stay in Montalcino
- Al Brunello≫ – a wonderful hotel in Montalcino with its own garden and a seasonal pool. The hotel has terraces and balconies with great views of the Val d’Orcia hills.
- Hotel Dei Capitani≫ – atmospheric villa-hotel in the heart of historic Montalcino. Spacious rooms with wonderful Tuscan views. The hotel serves a varied, very tasty breakfast. The pool overlooking vineyards is a highlight of the hotel. There’s its own parking for guests with cars.
- Podere Brizio≫ – wonderful location and stunning views, the hotel has an excellent restaurant serving Italian cuisine and house wine.
Pienza
The most enchanting views of the valley open from the walls of Pienza. The local pecorino cheese is insane. Also try Pici pasta with truffles, and later go see the sunset and the wonderful view of Mount Amiata, rising over the Val d’Orcia valley, with its green hills, cypresses and the winding ribbon of road.
Where to stay in Pienza
- Agriturismo Marinello≫ – the agriturismo has a stunning location with a view of Pienza atop the hill. A nice pool will cool you in summer heat and provide fantastic views over the valley and sunset.
- Piccolo Hotel La Valle≫ – the hotel is very conveniently located for travelers by car—there’s private parking. Nearby is the old town with restaurants and shops. The hotel is on a hill—rooms and the open veranda offer a great view over the valley.
- Relais Il Chiostro Di Pienza≫ – incredibly beautiful location in Pienza, rooms with a wonderful view of the Val d’Orcia valley.
Here’s a very tasty and affordable bar for you—BAR Panini Ai Sapori Di Una Volta, where locals and truck drivers stop for a snack. Here you can buy panini (sandwiches) with porchetta, salami, cheese made by the bar owners themselves. The porchetta here is the tastiest in the Val d’Orcia valley (according to locals). Delicious panini cost 2–3 Euros.
Located not far from Pienza—Strada Statale Nord 2 Cassia, 20, 53023 Gallina SI, Italy
Montepulciano
Montepulciano—the city of the Etruscans and the homeland of the Medici family. “Monte” means mountain in Italian, and the city on the hill is covered in endless ascents, descents, and incredible valley views. This city is a bit bigger than Montalcino, with astonishingly beautiful palazzos.
Here they make Italy’s oldest deep ruby red wine—legendary Vino Nobile di Montepulciano. It’s a classic tested over centuries. You can go on excursions and masterclasses at wineries, taste the wine, and buy a bottle as a gift.
It’s worth staying in Montepulciano for at least a couple of nights. Stay at any hotel in the center. Or choose an agriturismo on the outskirts, so you don’t have to deny yourself an extra glass of wine and can greet the morning among vineyards covered with dew.
- Visit the main square Piazza Grande and take a photo by the ancient well.
- The city tower has an old clock with an Italian Punch (Pulcinella) who strikes the bell with a hammer every hour.
- Visit the local viewing platforms for breathtaking views of the valley.
- Step inside the main Duomo (or the Cathedral of Santa Maria Assunta).
- Climb the tower of Palazzo Comunale: from there you get an excellent view of the Great Square and the entire city.
Where to stay in Montepulciano
- Il Buonumore≫ – Excellent location—the hotel is in a great spot in Montepulciano’s main historic district, next to all shops, restaurants, and many wineries. Large comfortable rooms, great for family couples.
- Hotel Panoramic Montepulciano≫ – spacious clean rooms, comfortable beds, large bathroom, beautiful view, large pool and relaxation area, classic sweet Italian breakfasts.
- Tenuta Santagnese≫ – Beautiful romantic farmhouse with historic wine cellars, where you can take part in wine tastings.
Arcidosso
We chose this small town not by chance—it’s completely non-touristy, ancient, and authentic. Here you can immerse yourself in rural Tuscany—which we gladly did. So what exactly did we do in Arcidosso? We stayed in an old house where Thalassa Locanda B&B e appartamento is now located.
We went for morning coffee with the locals, watched young men and women drink coffee quickly at the bar, and old men take their time and stretch an espresso out over two hours. Then we would go to the little market for juicy fruit and fragrant tomatoes. During the day we drove through the Tuscan hills and in the evening went for dinner at Osteria Bastarda Rossa, owned by the host of our apartment.
Tuff towns – Pitigliano and Sorano
In southern Tuscany on the border with Umbria are the tuff towns of Pitigliano and Sorano. They were built on the edge of wooded canyons of yellow sandstone. The towns stand on tuff cliffs, surrounded by towering ravines.
From the outside, they look like impregnable fortresses, but inside there are narrow winding streets, stairs lined with flower pots. Bells ring, their chime echoing throughout the area, and hundreds of pigeons take off from the tiled roofs. In the evenings, the walls and streets of Pitigliano and Sorano are softly lit with yellow lights. It seems as if they’re floating in the sky through the dark night into uncharted realms.
Accommodation in Pitigliano:
- Casa Messi≫ – Located right in the center of old Pitigliano, just a few steps from the Jewish Museum and the main square. Exceptionally cozy little apartment with an inimitable touch. Note—the car must be left in the parking lot outside the old town.
- il Cantuccio≫ – great place to stay for a city visit. The property is in a very old building, tastefully renovated, and is very close to a variety of restaurants. The owner provides information for the best car parking in town.
Sea in Tuscany – Beaches in Grosseto
In Tuscany, there are not just hills, medieval towns, and wineries. There’s also the sea, which I hadn’t even thought about at the time. But we spontaneously decided to celebrate our daughter’s birthday by the sea. So we chose the direction of Grosseto—huge semi-empty sandy beaches.
Twelve kilometers from Grosseto is the Marina resort area. Here there are long spacious sandy beaches and a pine forest nearby, calm sea. For summer holidays there are campgrounds and sea attractions. The beaches are very long and most of them are wild—there’s room for everyone.
Where to stay in Tuscany
There are so many small towns in Tuscany, you’ll want to peek into all of them—you can stay anywhere overnight. Or in an agriturismo—private mini-farms where they grow vegetables, fruit, livestock, and offer rooms for tourists who want to experience calm and delicious Tuscan life.
Agriturismo—in my opinion, is the best accommodation option if you want to immerse yourself in the rural life of Tuscany. If you’re planning a trip in the summer—choose agriturismo with pools, as it gets very hot here during the day.
B&B—Bed and Breakfast—these are basically apartments, but many offer breakfast included. For me, breakfast is an extra option, as it’s great to go out for coffee and pastry in Italy in the morning. Or make coffee yourself with fresh baguette and pâté, as apartments have their own kitchen.
Book accommodation in Tuscany⋙
Useful Articles and Links:
- Where to see lavender fields in Europe – the best locations for photos
- Velvet season – the best places to relax at sea in September
- The best things to do in Pisa in one day
Find hotels – Booking.com
Touristic insurance – Hotline.Finance
Rent a car – Rentalcars.com
