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Most beautiful scenic drives through Umbria and Tuscany

| Barbara Kollmann |


My personal most beautiful scenic drives through Umbria and Tuscany consist od the following day trips. Each of them starts at Casa Lauretana. They are a wonderful mix of winding routes through hilly landscapes, panorama and culture. Some of the routes are long, others take less time – but they all provide you with new and interesting impressions.

This you can find in Umbria AND in Tuscany

Some routes lead you into Tuscany. You will drive on well-tended roads, many of them lined with cypresses. And you will see that picture-perfect landscape that you know from the postcards: enchanting views, rural charm and beautiful medieval towns. 

wine & castles

But you may also drive through „my“ small, unvarnished and water-rich Umbria, with its light green, dark green, olive green, moss green, shamrock green, evergreen meadows, forests and hills.

Umbrian landscape also has its charm!
Panicale, most beautiful gem in Umbria
Lake Trasimeno in April

No matter which road or wich region you chose – you will spend a wonderful day!

☛ Please don´t forget your camera!

Tour 1 – to the West (approx. 130 km)

Route: Acquaviva – Montepulciano – Pienza – S. Quirico – Bagno Vignoni – Bagni San Filippo – Radicofani – Sarteano – Querce al Pino – Montallese – Tre Berte – Salcheto – Pozzuolo.

Val d´Orcia

The shortest way to reach Montepulciano is by the little town of Acquaviva. Once you have reached Montepulciano you drive all around the hilltop town following the signs of Pienza (SP 146).

The route section between Montepulciano – Pienza and San Quirico is considered one of the most beautiful and scenic drives in Italy. You will „sail“ on well-maintained roads into the famous Val D’ Orcia valley, in the province of Siena, while enjoying an incredible and enchanting panorama.

Montepulciano – Pienza

Once you have left Montepulciano you might try and pick one of the few Parking lanes on the right side to take a look back at this impressive, medieval town most famous for its wine, because from this side Montepulciano, standing high atop a hill, presents itself really nice.

Back on the road to Pienza, after a few kms, on your right, you will find the Cugusi cheese dairy (Caseificio Cugusi Silvana – daily open 8:00 a.m. – 1:00 p.m., 3:00 p.m. – 6:30 p.m.). If you are looking for some high quality Pecorino cheese, this is the place to be.

Before reaching Pienza, on the right side, you can admire and buy iron work at Ferro Battuto Biagiotti (opening hours: 9:00 a.m. – 1:00 p.m., 3:00 p.m. – 7:00 p.m.).

The Coffee Roasting named Torrefazione Caffé GM (open Mondays to Saturdays 9 a.m. – 6 p.m.), which is located a few meters after Biagiotti, is also worth a visit. Here you can drink (and also buy) very eco – friendly coffee that came all the way down from South America by sailing boat.

S. Quirico d´Orcia – Bagno Vignoni

Please leave Pienza on your left and continue towards S. Quirico d’Orcia. Photographers, wanderers, sentamentalists and romantics, please pay attention: Amongst the impressive images of the evocative Tuscan countryside, you are likely to spot one particular little chapel popping up time and time again: the Chapel of the Madonna di Vitaleta.

Cappella di Santa Maria di Vitaleta

This little gem, framed on both sides by cypresses and, embedded in gentle green hills, is one of the most photographed churches in Tuscany. Un fortunately it is not very interesting, even though it dates back to the 12th century. So what is so special about it? It is its magical sight and the picturesque, peaceful surroundings that get under your skin!

How to reach the Cappella: About 5 km after Pienza, you can follow the little wooden sign on the left-hand side of the road and turn down a dirt road to the chapel. It leads you to a parking lot and from here you will have to walk the last kilometre down to the building (you can’t get any closer by car as it is fenced off.)

You are driving along the most scenic roads in Tuscany

Back on the SP 146 linking Pienza to San Quirico d’Orcia you skip S. Quirico d´Orcia as you are now heading south, towards the Via Cassia (SR 2); the construction of this famous old Roman road dates back to 241 BC.

Our next stop is called Bagno Vignoni, another unexpected little Tuscan gem. 

This Etruscan thermal village despite wars and ravages, is kept unchanged and you can enjoy a beautiful atmosphere with lots of cafés, bars and restaurants. Visitors can admire the famous Piazza delle Fonti (Square of sources ) which is a rectangular tank of 16th-century origin, containing the original source of hot thermal water coming from the underground and having volcanic origins. This pool is no longer used by the public.

The oldest surviving pool is fed by underground thermal springs

Bagni San Filippo

Back on the Cassia we drive another 20 kms to reach a small hamlet called Bagni San Filippo, which you have to visit because of its open air thermal cascades. Fosso Bianco is the name of the warm, natural sulfur pools and their impressive calcium formations found in the forest nearby. This natural spectacle has free access for everyone.

Radicofani – Sarteano

If you are still in the mood to visit another small Tuscan highlight, once back on the Via Cassia again, heading South again, please take one of the coming options to the left, towards Radicofani

The monumental castle on top of a hill catches your eye well before reaching the hamlet. From this fortress you have a fantastic view over large parts of Tuscany (and the St. Francis´ Way). History lovers should also visit the museum inside the castle complex. Radicofani itself has very well-kept houses, churches and palaces, it is fun to stroll through this beautiful little village, enjoying the fantastic view again and again. 

Radicofani centro storico

From Radicofani your trip goes North east, you take the SP 478 into the direction of Sarteano, which has a cute old town too, and Chiusi.

Querce al Pino – Petrignano del Lago

In Querce al Pino you leave the SP478 and keep on the SP 146 towards Chianciano Terme until you can turn right onto the SP50, indicating the direction of Lago Trasimeno.

In Località Quattro Poderi please turn left at the traffic lights and stay on this somewhat boring SP 326 road which runs in parallel to the motorway A1. You will drive through the small towns of Montallese and Tre Berte until you reach Salcheto. Here you have to turn right onto the SP 454 which brings you back to Pozzuolo and Petrignano. (Attention: permanently installed Autovelox boxes between Montallese and Tre Berte)

Cabernet-Sauvignon, Merlot or Sangiovese?

Getting hungry?

From all the many cafés, bars and restaurants in Bagno Vignoni, I prefer the Osteria del Leone, Via Dei Mulini 3 (12.00pm – 3.00pm and 7.30pm – 10.30pm, closed on Mondays. Reservations by telephone are recommended in high season. Tel: 0577 887300 ).

The reviews of the trattorie and restaurants in Radicofani are actually all good; I can recommend the nice little bar – enoteca – bruschetteria named “Al Tocco“  on Piazza S. Pietro (Tel: 0577 887300).

Tour 2 – to the North (approx. 135 km)

Route: Petrignano del Lago – Tuoro – Montone – Città di Castello – Palazzo del Pero – Castiglion Fiorentino – Camucia – Petrignano del Lago

Today you will get to know a very different Umbria from the one you have met on Tour 1.

Passing through Ferretto you drive towards Raccordo autostradale 6 Bettolle – Perugia. About 1 km before the highway access, when you see the Ristorante “La Badiaccia” on your right, please turn right and cross the small village of Borghetto, in direction of Tuoro.

The road passes under a railroad line and runs parallel to the freeway for a short stretch. Then it slightly climbs and at the T-junction next to the Tapas Bar “Punta Bella” you turn right and follow this road until you reach the sign of Tuoro indicating to the left. You turn left and the road winds uphill around Tuoro. After 6 km, on the ridge to the right, you will find the Bar (Restaurant and Pizzeria) “Lo Scoiattolo”, a popular meeting point for motorcyclists and other excursionists.

This is a pleasant place to have a cappuccino, an aperitivo or even a meal as you can sit outside and enjoy a wide view over Lake Trasimeno.

From here, the road winds downhill for another 6 km, in many tight turns and through a large oak and chestnut forest. Before entering Lisciano Niccone, and still following the signs for Città di Castello, please keep left at first and then stay on the main road, which turns right in Mercatale. This road now, with only a few bends, for about 20 minutes will lead you along the Tuscan-Umbrian regional border. At first you will be surrounded by sunflower fields, but the further north you go, the more tobacco plantations you will see. Did you know that tobacco has been grown in Umbria since 1575? In Niccone please turn left towards Città di Castello, and after about 4 km don’t miss the turn-off on your right side leading you to Montone.

One of the well-preserved ancient city gates

This small, very well-kept settlement, dates back to the 10th century. With its nice alleys and a well-preserved castle called Rocca di Braccio, Montone is considered one of the most beautiful towns in Italy.

This alleyway leads from the Rocca down to the main piazza in the center

The centro storico is a wonderful place to sit and have a cappuccino, an aperitivo, or even lunch.

The old city wall
Looking into the nearby region Le Marche

From Montone you can quickly reach the historic Roman town of Città di Castello. It is situated on the upper Tiber river and famous for its white truffles. You can find many parking spaces on the outside and along the city wall. From here you can reach the centro storico in a very short time. You will be amazed how Renaissance influenced Città di Castello is.

Shady parking spaces, a sidewalk, the city wall

Even Pliny the Younger praised the elegance and beauty of this city. So many sight to visit here, the Duomo, Palazzo del Podestà, various towers, the Pinacoteca of Palazzo Vitelli alla Cannoniera (they offer good guided tours) with its enchanting garden, the 1799 printing press (Tipografia Grifani Donati) etc.

The cilindric tower, one of the city symbols

You should not miss the two museums set up in old tobacco halls in honor of Alberto Burri (1915-1995). Burri is one of Italy’s greatest contemporary artists and has left a large part of his works to his native town Città di Castello. For more informations please check:

Those interested in small furniture and antiques can visit the town’s Retrò market which takes place every 3rd Sunday of the month. The prices here are much more affordable than the ones at the famous and always very crowded antique market of Arezzo.

Torre del Vescovo (Bishop´s tower)

My personal tip for a lunch in summer is the Trattoria “Il Cacciatore” in Via della Broccina 3 (or is it number 10?) There is room for only 4 tables outside in this cute, very small and shady dead end road, so a reservation is highly recommended: 075 8520882 or 3475727308 (closed on Tuesdays and Wednesdays).

After your visit of Città di Castello, please continue north on the SS3bis (towards Sansepolcro) until you see a sign indicating Lerchi which leads you to the left. Now you are driving on the SS2bis, heading west, towards Arezzo, or Cortona. (You will spot a small road parallel to the Superstrada, which you are driving on, but we recommend not to take this small road, as this section runs through uninteresting woods and you would lose a lot of time.) There is one last highlight waiting for you before reaching Castiglion Fiorentino: Citerna.

Coming from Lerchi, after about 6.5 km you will see the first sign to Citerna on the right. If you miss this turnoff, there are two more to follow. The medieval village of Citerna, much frequented by pilgrims, is one of the most beautiful villages in Tuscany and is listed in the guidebook of the “Borghi più belli d’Italia”. The little detour is worth it!

The working antique clockwork on the village tower in the centre

After visiting Citerna you drive back to the SP221 until you reach Palazzo del Pero, a tiny, completely inconspicuous place. Here you will have to leave the SS2bis Superstrada and turn left onto the winding, small, seemingly never-ending forest road that leads you to Castiglion Fiorentino. It may well be that you won’t meet a soul while driving through these lonely woods.

You enter Castiglion Fiorentino from the north. When it is very crowded I recommend you park your car directly on the huge parking lot, which you will inevitably pass. Otherwise you can find a parking lot a little further down, near the old city gate called Porta Fiorentina.

Porta Fiorentina

Castiglion Fiorentino was founded by the Etruscans as early as the 4th-5th century BC., and parts of the city wall are still very well preserved. Again, so many sights to visit here, the Palazzo Pretorio, the Pinacoteca, which includes the Church of S. Angelo, the Monastery of S. Francesco, the Logge del Vasari, etc.

Looking north-east and to the Church of S. Giuliano

After entering the city gate and climbing up the hill straight ahead, you will reach the Piazza del Municipio with the lovely Antico Caffé La Posta, offering caffé, aperitivo and small dishes. Up here, time really seems to stand still and one enjoys peace and a wonderful view.

From Castiglion Fiorentino the main road ( SR71), which is quite busy and not very attractive, will lead you to Camucia. Now the Via Lauretana will bring you via S. Lorenzo and Centoia back to Petrignano del Lago.

Tour 3 – to the South (approx. 122 km)

Route: Petrignano del Lago – Gioella – Villastrada – Moiano – San Casciano dei Bagni – Sarteano – Querce al Pino – Porto – Petrignano del Lago

Again we start from Petrignano

work in progress