Explore Tuscany by car

Tuscany is one of those magical parts of the world, where you are immersed in magical views of olive trees, grape vines, Cypress trees and villas that all look old, well maintained and so in keeping with their environs. You can never tell if a building is new, old or really, really old, and which part is added or changed, it leaves you with a timeless feeling. It also makes you wonder why we build the way we do in New Zealand.

If exploring Tuscany by car, we would recommend that you have 7 days.  Driving is quite easy in this area, the roads are easy to navigate and a car enables you to get to more remote wee towns and areas.  The distances between towns are surprisingly small.

Following is some info on our favourite villages, if you are based in a villa you will most probably be between Siena and Florence in the Chianti area – this is a great location and most villages are within easy driving distances.

Suggested day excursions:

A full day in Siena.

The small Chianti villages of Castellina in Chianti and Greve are very popular.

Drive to the West and you can visit San Gimignano, Pisa and Lucca.

Drive to the South and you can visit the wine towns of Montepulicano and Montalcino with perhaps a quick visit to the tiny town of Pienza.

Drive to the East and you can visit the famous town of Cortona and Arezzo.

A longer driving day could get you down to Assisi, Spoleto, Todi, Montefalco and perhaps Orvieto in Umbria.

Siena and San Gimignano are two must sees.

Siena – this is an absolute must visit and is a good location for 1-2 nights.   The main sights cluster around the fan-shaped Piazza del Campo (known as Italy’s loveliest piazza).   Do visit the Duomo and admire the beautiful black and white striped marble pillars and the ceiling that is painted to resemble the night sky.   Palazzo Pubblico – the Gothic town hall needs a visit, the bell tower is stunning.  The Siena School of Art is a must visit.  It is next to the Palazzo Communale (Town Hall and Bell Tower) which is worth the climb for the views, but quite steep.  The Museo Civico is a series of rooms by artists of the Sienese School.  This gives a great history and documents the early art of showing how they perfected drawing/painting the human body and the ability to paint in depth (3D), it’s a must visit with some fantastic art.   We recommend that you spend the day up to 3pm in Sienna, then go back to the villa for a swim and then back to Siena (only 5kms) for 5- 7pm when all the Italians are out to socialise and promenade.  Siena is home to the famous Alissi  (Corso de Fiori) shops – great to buy a stove top coffee machine.  Visit Antonio’s Deli for meats, cheeses, Grappa and homemade goodies at Antica Pizzicheria al Palazzo della Chigiana. Via Di Citta, 93/95 23100 Siena.

They don’t do branding and marketing in Italy like we do, Siena is the perfect example where you look down a street and think there’s nothing down there (as in shops).   As apart from Pharmacies there are no signs, not even sandwich boards, the streets look just the same as 100 or 300 years ago.  So you wander down anyway and find shops for tobacco, linen, shoes (oh the shoes), coffee machines, kitchen accessories (lots of Allesi).

San Gimignano – another perfect wee hilltop town that was once home to around 76 towers, just 14 remain today.  Do climb a few, you will get the most magnificent Tuscan scenery shots.  Do visit the 12th Century church Collegiata in Piazza del Duomo – it has magnificent frescoes adorning the walls.  The north aisle frescoes depict 26 episodes of the Old Testament, the opposite wall the Life of Christ whilst the back of the church features scenes from the Last Judgement.  You will also get to admire the beautiful striped marble pillars.  The church is kept in the dark to protect the frescoes, so when you are ready to view the frescoes, pop some coins in the meter and the lights will come for a short time.  (It is worth it).

Opposite the church is the Torture Museum (not for the fainthearted) a fascinating look at what man (in the guise of religion) is capable of.   As with many of these wee towns, bus loads of tourists are trucked in each day so staying overnight allows you to explore the town after hours!  Alternatively we highly recommend an early start so you arrive here by 9am and have time to enjoy it before it gets too busy.

Pisa is very much a drive in, have a good look at the Leaning Tower and the exquisite Duomo and Baptistry and leave – there is little else to tempt you!  (Combines well with a trip to San Gimignano or Lucca). Also is good to drive by Pisa if you are driving between the Cinque Terre and Tuscany.

Viareggio – a coastal town that is a very popular resort area – good if you want a bit of beaching.

Montalcino – you will be awestruck as you wander and look, seeing the locals go about their daily life (your first day sightseeing is often Sunday as villas are rented Saturday to Saturday) so it’s a pleasure to watch all the families, young to old off to Mass (very Catholic). They all smile as you pass, stop for coffee (as you do in Italy) and it’s always exceptional. (It’s cheaper to stand at the bar than to take a table, and a table outside is sometimes dearer but hey the people watching is worth every penny.)

Montalcino is situated in the heart of the Brunello vineyards – so great wine tasting and excellent restaurants.  The 14th C fort has impressive ramparts and has a wonderful Enoteca (wineshop) for tastings.  Buy a bottle of wine and some picnic goodies and enjoy a late afternoon picnic on the ramparts.

Montepulciano  – also located in the wine regions, is a must visit south of Siena, very hilly and remarkable for its wine cellars and town square. A wine tasting is a must.   From here drive to The Abbey of Sant’Antimo – a fabulous old 780 AD Carolingian Church – it sits amidst fields of poppies and cypress trees – very scenic!  This is a highlight as only those with cars or on organised walking tours are going to see it.

Pienza – is a lovely wee village and is referred to as a real renaissance jewel, it is located in the south near Montepulciano and Montalcino and is famous for its Pecorino Cheese.

Arezzo – one of Tuscany’s wealthiest towns – famous for jewellery.

Cortona – is one of the oldest and most scenic Tuscan hill towns and it is where Francis Mayes is based.   Cortona on a Sunday evening is the place to be, it looks like there is some kind of celebration on as so many people driving up the hill and parking to walk the rest of the way to this hillside town. It’s one of those places that really comes to life from 5-7pm and all the people strut up the main street to be seen. Lots of Romans out for a day’s drive, the Italians like no other are proud of who they are, what they wear and they like to be admired, they thrive on the cafe watchers.   It is a great experience and a highlight.

Greve – right in the heart of the Chianti regions, this is a favourite wine area.  It is one of our favourite villa spots.  As it is flat it is a good option if you have mobility issues or a pushing a pram!  Great cafes and easy carparking.  Still feels very much like a local village.