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Tuscany’s Hilltop Treasures

by Alan Gow  |  June 2019  |  Italy

Tuscany evokes alluring images of vineyards, olive trees, good food, picturesque towns and loads of sunshine.  There is a good reason why Tuscany is one of the most visited regions in Italy – it is absolutely gorgeous.

Siena, San Gimignano, Montepulciano, Cortana, Pisa, Lucca…. the list of spectacular historic towns is seemingly endless. Chianti, Brunello di Montalcino and Vino Nobile di Montepulciano… the names of the unique regional wines just roll off the tongue as easily as the wine flows down the throat.


Tuscany’s Hilltop Treasures

We had three weeks, in May 2019, to nosey around this little patch of paradise and visit some of the well-known, and not so well-known beauty spots.  I confess that by the end of this time, seeing yet another ancient walled hilltop town ceased to be the thrill it was at the start.  There was always something however that was unique and made the effort worthwhile.

I’m not going to bore you with a detailed regurgitation of Dr Wikipedia’s facts about each place we visited.  Instead, there will just be a few pictures and maybe a sentence or two to explain the individual specialness (if that’s a word), that we found there.

For a change, we were not staying in our motorhome in Tuscany because Betsy was in for repairs. We stayed in AirBnBs in three towns and used them as bases for exploring others.

We will still give you some likely spots to park up your motorhome for free.  We found most of these, as usual, on Park4Night.  No guarantees but they looked good to us so should work unless the local authorities have an about face and start restricting the parking.

Colle Val D’Elsa

The views from this charming medieval walled hilltop town immediately captivated us.  The sturdy ancient stone walls, the delightful Tuscan countryside and the fresh vibrant spring flowers welcomed us to Tuscany. The low number of tourists visiting this less well-known jewel was delightful.

There is a large car park where you can park overnight near the old town (GPS 43.4226, 11.1140).  Most of the parks are better suited to smaller campers but there are some slots where you can reverse your overhang out over vacant ground (bring your ramps). Park4Night has some other places in the new part of town which may be better for bigger vehicles.

View of Colle from the old Convent

View down the beautiful Val D’Elsa Valley

Old Colle and the Church tower

Typical archways and narrow alleys

Plants anyone?

San Gimignano

The USESCO listed San Gimignano is one of the most well-known of the Tuscany hill towns and as such was brim full of visitors even this early in the tourist season (May).  The 14 tall towers that are a hallmark of the San Gimignano skyline were built by the rich families between the 11th and 14th centuries as a symbol of their power and wealth, and to provide protection from other families.

To watch a UNESCO video click here.

Not far from here we had a great day out at Ulignano truffle hunting, wine tasting and scoffing delicious food.  Great value and a special day out that we thoroughly recommended.

There is an authorised camper parking area at GPS  43.4521, 11.0556  however at €1/hour (€15/day) it is pricy for a longer stay.  You can use the services there without going into the parking and a free alternative parking can be found on the other side of town at GPS 43.4716,11.0285. This place looked like it would be fine for overnight however we stayed just a few hours.

San Gimignano spotted through fresh spring growth

Typical towers of San Gimignano

Busy, narrow streets and arches


Described as one of the most perfect examples of a medieval town, the UNESCO listed historic centre of Siena blends almost seamlessly into the contours of three hills.  For us riding our electric bikes, it also seamed to have the steepest hills of any of the Tuscan towns.

To watch a UNESCO video click here.

A parking area just outside the walls allows an opportunity for campers to park overnight but there is a bit of a gradient involved so ramps recommended (GPS 43.327561, 11.335099).  We didn’t stay here but spoke with other travellers who slept here without problems.

Siena and the Cathedral from the Medici Fortress

Piazza de Campo famous for the annual horse race

Basilica Cateriniana San Domenico

World Class Siena Cathedral


We spent several nights in an AirBnB just outside the medieval town walls and had several opportunities to soak in the sights and feelings.  Of special interest were the underground towns carved out by the winemaking families of the region.  These chambers with interconnecting passageways were (and still are) used for making and storing the famous local red wines and cheeses. 

Panoramic view from the town walls

Wine cellar in the underground city

Montepulciano main piazza

Enter the underground city here

One of the gates into the town

Montepulciano walls and houses


Pienza is a little off the beaten tourist track but also features a historic centre listed by UNESCO due to it being the first example of Renaissance-era town planning.  The pet project of the Pope at the time.  This resulted in a beautiful town square while still preserving the older medieval structure and walls of the town.  Pienza has been referred to as the jewel of Tuscany.

To watch a UNESCO video click here.

There are a couple of potential overnight spots for campers including these authorised camper parking spaces at GPS 43.079949, 11.673309.

Pienza main piazza with the Cathedral

Inside the Pienza Cathedral

Stunning views over the Tuscan countryside

Spring flowers among the ancient buildings

Back streets and cafes

Narrow cobbled streets with few tourists

Frescoed gate in the town wall


Another delightful walled town is Cortana with now-expected imposing walls, narrow streets and medieval buildings.  The unexpected highlight was the gorgeous interior of the Basilica Santa Margherita which was reached after a very long and steep climb up ancient stone roads and paths.  Our bikes could only take us so far.  We love being surprised when we walk into somewhere new and have that ‘blown away’ feeling.  There are some possible overnight parking spots for motorhomes as you drive up the hill. We found a small slot at GPS 43.2733, 11.9860. There was an authorised campervan parking here but that was closed for renovation when we visited and may or may not reopen (GPS 43.272985, 11.987823)

The view from the walls of Cortona 

Steep road by the walls leads to the Cathedral

The Basilica di Santa Margherita is worth the walk

Tuscan cobbled streets and art galleries abound

Old buildings and new flowers

Looking up the hill to the town is like looking at a fairy-tale


Arezzo was one of those pleasant surprises because you don’t read about it being a top tourist attraction.  However, it had everything you would want.  A great spot to park a camper not far from the entrance (GPS 43.4725,11.8831 ), a stunning cathedral, Medici fort and plentiful narrow alleyways, piazzas, old buildings, parks and shops.

The gorgeous Arezzo Cathedral

The Cathedral frescos are mesmersing

Monument of Francesco Petrarca

View from the Medici Fortress over the cemetery and beyond

Bagni San Fillipo

The small town of Bagni San Fillipo is famous for the natural hot springs that flow close by.  These have been left largely undeveloped (thankfully).  A visit here allowed us the rare chance to sit in piping hot thermal water, surrounded by trees and towering structures of thermally deposited minerals including the renowned “Balena Bianca” or White Whale.  The best part is that it was all free of charge (apart from the parking).  It is a popular destination but we arrived later in the day and spotted some English people we had met a few days earlier in Siena.  They invited us to sit in ‘their’ pool, which was the best spot.  Nice having friends in high places.

The massive “Balena Bianco” (White Whale) natural sculpture

Soaking in a warm stream of thermal water


This was another of the less visited Tuscan towns and one that we immediately liked. We stayed high up in sports ground parking area not far from the walls (GPS 43.3976, 10.8616) and close to great views of the surrounding countryside.  The Medici fort here is still used as a penitentiary so we couldn’t visit.  The large weekly market and the fantastic outlook over the partly excavated Roman Theatre were particularly memorable.

Early morning views over misty Tuscan landscape

A well preserved Roman Theatre is a highlight

Baptistery of San Giovanni

The old Etruscan Gate

Where are the tourists?

Volterra views

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