If you're looking for some new destinations and you want to travel surrounded by rolling hills, possibly rent a car and chose Siena as a base for your holidays in Tuscany. Any trip to Tuscany isn’t complete without some day trips to discover the hidden gems along the way. The ideal way to visit these places around Siena is by car, but you can also take advantage of a guided tour or you can check the public transportation’s timetable. The main advantage of visiting Tuscany by car is that when you see a glimpse of a picturesque view you can stop and take a photograph.
It's worth travelling the 70 kilometres that separate the two cities and to abandon the peaceful countryside around Siena for one day to visit the birthplace of the Renaissance, the city of art par excellence. Visiting Tuscany and skipping Florence is a pity. It is easy to reach it from Siena: there are frequent trains and a bus service that connect the two cities, allowing you to stop by for a quick trip. Read more about Florence: What to see and do in Florence and One day in Florence.
Monteriggioni has practically remained the same as it was in the Middle Ages and its distinctive design gives it a uniqueness that is worth exploring. This perfectly preserved medieval village boasts walls, fourteen towers on square bases, a central peculiar square, and charming streets that seem to come from the past. Read more about Monteriggioni.
San Gimignano deserves the fame that it has received worldwide. Be enchanted by the towers that rise up to the sky and get lost in the Manhattan of the Middle Ages. Known as “the city of the 100 towers”, San Gimignano ownes an unforgettable skyline and it’s a UNESCO World Heritage site. Reach it by car or by bus. Read more about San Gimignano.
This evocative part of Tuscany, situated between Arezzo and Siena, is characterized by rolling clay hills (the literal meaning of “Crete Senesi” is Sienese clays) and dotted with villages, cypress and oak trees as well as long-abandoned farmhouses. Around the Crete Senesi area you can also visit Buonconvento, Asciano, Rapolano Terme, San Giovanni d’Asso, and the stunning Monte Oliveto Maggiore Abbey. Read more about Crete Senesi.
Pienza is a living dream. In 1996, it was declared a UNESCO World Heritage Site and it is worth a visit for plenty of reasons: the magnificent views over the Tuscan Val d’Orcia, Piazza Pio II, and the streets with “romantic” names such as Via del Bacio (kiss street) and Via dell’Amore (love street). It also boasts culinary delicacies such as the famous "pecorino" cheese, pici pasta, and Cinta Senese sausages. Read more about Pienza.
The beautiful village of San Quirico d'Orcia sits atop a hill halfway between Pienza and Montalcino. It is located along the Via Francigena and you can visit the beautiful church dating back to 714, stop by a beautiful rose garden and get lost in its ancient, narrow streets. The main street called Via Dante Alighieri cuts trhrough the village. You can enter San Quirico through one of the four entrances along the walls and from there you can enjoy breath-taking views all over the Val d’Orcia, from the Monte Amiata to the beautiful hilltop towns of Pienza and Montalcino. For an itinerary on this area of Tuscany, read this post about San Quirico d'Orcia.
The hill town of Montalcino, completely encircled by fortified walls, is situated in the Val d’Orcia, a few kilometres from Pienza and the Crete Senesi and not far from Mount Amiata. Renowned for its world-famous wine, Brunello di Montalcino, it is also a fairy-tale place to spend a day immersed in Tuscany’s history and countryside. The must-see sights include the fortress, the Duomo, Piazza del Popolo and many other attractions which you can read about in this post.
Nestled between the Val D’Orcia and Val di Chiana, Montepulciano is a quintessential Tuscan medieval village known as “la perla del 1500” (the jewel of fourteenth century). Montepulciano boasts remarkable masterpieces of the Renaissance. It is famous worldwide for its Vino Nobile, but it is worth a visit especially for its splendid Renaissance art and architecture, such as the castle of Montepulciano, Piazza Grande, situated at the highest point of the town, the Cathedral of Santa Maria Assunta and many other things that you can check in this post about Montepulciano.
Monte Amiata is the highest extinct volcano in Italy. It stands 1,736 metres high and is situated in southern Tuscany. This area has it all: history, art, nature and culture, and it's the perfect place to go cycling, relaxing and exploring. Many unique medieval villages are perched on its slopes, close to pristine forests. Read more about Monte Amiata. And to visit many other places in the area surrounding Monte Amiata check out this post.
Chianti covers a large part of Tuscany, one of the most famous places in the world with its green rolling hills and beautiful landscapes. If you are looking for vineyards and olive trees as far as the eye can see, Chianti is the day trip for you. If you want to explore it by motorbike this itinerary is for you!