Planning a trip to Tuscany? Well, you’ve come to the right place! Not only is Tuscany one of my favourite destinations in the entire world, it also happens to be one of the most picturesque landscapes, perfect for a leisurely road trip through the iconic Italian countryside. And to make sure that you don’t miss any of the best spots, I’ve compiled a list of 9 photo-worthy locations that you simply cannot miss on your journey through Tuscany.
1 Florence
No Tuscan trip can be complete without a visit to the capital city of the region and the cradle of the Renaissance period – Florence. Home to some of the most famous Renaissance art works, including Michelangelo’s David and Boticelli’s The birth of Venus, this majestic city is a true treasure trove of art, history and culture. The biggest landmark that dominates the city skyline is the cathedral Santa Maria del Fiore, commonly known as the Duomo. The cathedral features the largest masonry dome in the world, which was engineered by the founding father of Renaissance architecture, Filippo Brunelleschi. Other marvels of architecture worth a stop include the Palazzo Vecchio and the neighbouring Uffizi Gallery, Ponte Vecchio with its array of glittering jewellery shops and Palazzo Pitti with its marvellous Boboli gardens. For the perfect postcard picture of the city, head to Piazzale Michelangelo on the southern side of river Arno. From there, you will be able to enjoy stunning panoramic views of the city’s picture-perfect skyline and, in case you didn’t have the chance to see the original sculpture at the Accademia Gallery, marvel at the bronze replica of Michelangelo’s David.
2 San Gimignano
An hour’s drive south of Florence lies San Gimignano, a charming medieval walled town, also known as the city of a thousand towers. This UNESCO World Heritage site is famous for its 14 medieval tower houses which are extremely well preserved. In the past, there were over 58 spires that rose over the town, each commissioned by San Gimignano’s wealthiest families, each wanting to display their power and riches. To properly experience a glimpse of medieval Italy, walk through the Piazza della Cisterna, climb the Torre Grossa for stunning panoramic views and sample the town’s renowned Vernaccia wine at one of the local wineries.
3 Siena
Not far from San Gimignano lies Siena, a gothic masterpiece of architecture and another highlight of any Tuscan road trip. The fan-shaped Piazza del Campo is the heart of the city, where the famous Palio horse race takes place twice a year. The square also connects three hills, where the rest of the city is situated so a stroll through the centre can be quite a hike in some areas. The stunning Siena Cathedral, with its intricate marble floors and impressive library is definitely worth a visit and so is the rest of the city, with its winding streets and charming cafes that exude medieval charm.
4 Montalcino
If you continue south from Siena you will soon enter Val d’Orcia – the rolling countryside that is part of UNESCO world heritage. And right at the beginning of this beautiful region is Montalcino – a fairytale hilltop town set within a full circle of fortified walls and watched over by a mighty castle of medieval perfection. Montalcino is famous for its wineries, especially the ones producing Brunello di Montalcino, one of Italy’s most prestigious wines. The town is small, so it can be easily explored on foot and the surrounding walls offer breathtaking panoramic views of the spectacular countryside dotted with vineyards, olive groves and lonely cypress trees.
5 Montepulciano
A bit further down the road across Val d’Orcia lies Montepulciano, another stunning hillstop town or as I like to call it, Montalcino’s bigger brother. Just like Montalcino, Montepulciano is a medieval town with a rich historic background. The town is full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners and boasts vast panoramas all over the wonderful Val d’Orcia and Val di Chiana valleys that surround it. Montepulciano is a great strategic base to explore this part of Tuscany as you can reach villages and towns on either side in a very short time.
6 Monte Argentario
On the southern tip of Tuscany lies Monte Argentario, a charming coastal resort overlooking the open sea between Italy’s mainland and France’s Corsica. The peninsula is connected to the mainland by three narrow strips of land, creating a unique and picturesque setting. If you are looking for stunning sea views, take the Strada Panoramica and marvel at the rugged coastline, dotted with hidden beaches, marvellous seaside villas and crumbling forts built by the Spanish kings who ruled the area around 400 years ago.
7 Pisa
No Tuscan road trip is complete without a visit to Pisa to see the iconic Leaning Tower. This world-famous structure is part of the Piazza dei Miracoli, which also includes the Pisa Cathedral and Baptistery. Make sure you spend at least a day in this incredible university city and explore not just the Leaning Tower, but also the surrounding streets with plenty of shopping opportunities and some great local restaurants. So why is the Leaning Tower leaning, you wonder? It is because of the soft ground underneath the building which could not properly support its weight. In 1990, the tower was already leaning for 5.5 degrees but has now been stabilised at 3.97 degrees thanks to remedial work between 1993 and 2001.
8 Lucca
Not far from Pisa you will find Lucca, a city renowned for its well-preserved Renaissance walls. Most of the attractions in Lucca today show its ancient history: from the trace of the Roman amphitheatre that can be seen in the shape of the Piazza dell’Anfiteatro to the archeological remains under the 12th century church of Saints Giovanni and Reparata. Lucca is one of the few cities who was able to preserve its outstanding military walls that surround the entire old town. Nowadays, the walls are actually a pedestrian promenade where you can take a stroll, a bike ride or simply rest from sightseeing on one of the many shaded benches that line the main walkway.
9 The occasional village
Although I could easily add another great destination to complete this list, I wanted to leave the last location undefined. As you will wander the rolling hills of Tuscany, I am sure that you will come across many smaller villages that are maybe not significant enough to deserve a mention next to the likes of Florence, Siena and Pisa, yet their charm and character will simply be too appealing for you to not have a peek around. I find that it is always best to leave some room in your itinerary for an occasional hidden gem that will make your Tuscan trip unique and unforgettable.
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