With silver-screen hits like “Eat Pray Love” and “Under the Tuscan Sun”, it’s no wonder so many Italophiles have been inspired to plot a romantic road trip through the endless vineyards and rolling hills of Tuscany. With world-class wine, sensational cuisine, an impeccable collection of art, and its abundance of charming Medieval villages, the region is an absolute bucket list favourite. In fact, there’s so much to see that one might have trouble narrowing down an itinerary.
Not to worry – leave it to the experts! We’re sharing our Top 6 Tuscan Getaways, and we’re sure you won’t be disappointed.
1. The Magic of Siena Awaits You
Siena’s epic Duomo is but one of the town’s sights that will have you agape in wonder
Just 30 miles south of Florence, the city of Siena makes up a grand UNESCO world heritage site, complete with cobblestone alleys and Medieval monuments. This destination allows very little car traffic, adding to its timeless charm, and is so small that its main sights can easily be visited in just one day’s time.
Follow the winding streets to Piazza del Campo, admire the Torre del Mangia bell tower, savour a moment in the Basilica of San Domenico, and sip the local vino. Aimlessly wander the corridors of the Museo Civico, Pinacoteca Nazionale di Siena and Palazzo Pubblico – or take out all the guessing work and book a Siena Day Trip!
For an extra special experience, visit in summer to attend “Il Palio”, the annual summer horserace, when bareback horse riders race around the city’s main square, religiously on July 2nd and August 16th every year.
2. San Gimignano, Tuscany’s ‘Manhattan’ of the Middle Ages
The spectacular view from the top of the Torre Grossa in San Gimignano
Once you pass the ancient city walls into San Gimignano, you will quickly discover why it is often referred to as the “City of Beautiful Towers”. There are 14 of them, in fact, painting the horizon like medieval skyscrapers. The city center is another of Italy’s incredible UNESCO World Heritage Sites and is renowned as one of the most well-preserved medieval towns in the country.
In the space of a few hours, you can cross off the city’s highlights, including the Museo Etrusco, the Museo Archeologico, and the 12th century Collegiata di Santa Maria Assunta. Don’t forget to try the local specialty, “cinghiale” (wild boar meat) in one of the best pasta dishes you’ll ever taste! Want to skip the planning? How about a guided Day Trip to San Gimignano with us?
3. The Sensible Tuscan Charm of Lucca
The town of Lucca is full of quaint and elegant surprises
Though Lucca doesn’t ring any familiar bells for many, it was actually Tuscany’s capital until the late 10th century. Nowadays, not far from the more famous destination of Pisa, the city walls envelop a gorgeous Renaissance village with many churches and picturesque corners to explore.
Nature goers can opt for a walk or bike ride through the greener pastures while art lovers check out the city’s dazzling duomo and bell tower. Visit between March and November to experience the Annual Festival of Italian composer Giacomo Puccini, who was born here, with concerts taking place every single night.
4. Montepulciano: Gem of Brick & Stone in an Emerald Sea
No trip to Tuscany is complete without exploring the essence of the region in Montepulciano
If “postcard perfection” is what you’re looking for, look no further than Montepulciano. The stunning city of red brick and terracotta tops a towering limestone ridge at a remarkable 600-meter altitude. Once you enter the city walls, endless Tuscan panoramas fade off into the distance in every direction.
Even on a brief visit, you can’t miss the Church of Sant’Agostino, the Church of San Biago, and the beloved Pulcinella Tower. If you’re left longing for more art, head to the Palazzo Nobili-Tarugi or Palazzo Cervini and don’t forget to stop in the Piazza Grande for a glass of Montepulciano’s famous wine. If time permits, consider a tour of a local vineyard, too!
5. If Tuscany Were a Queen then Florence Would Be Its Crown
The dazzling Arno River curves under Ponte Vecchio through the historic center of Florence
What would a trip to Tuscany be without a stop in Florence? It would be incomplete, to say the least. The countryside towns of Tuscany will swoon you with their slow pace and simplicity, but Florence will whisk you into a magnificent adventure, enticing all of your senses.
The city boasts one of the greatest art collections in the world, along with a fantastic array of Renaissance and Gothic churches. It’s the home of gelato and the prime place for an authentic Fiorentina steak! Try some of the local wines and stroll the pedestrian streets – you’re bound to wander into some pleasant surprises. Check out our Florence tours for some idear.
6. No Place in Tuscany Provides New Perspectives Like Pisa
You may well bend your head with curiosity in Pisa, but the simple truth is beauty isn’t perfect!
Everyone knows Pisa is a great destination for a creative selfie with a leaning tower but, the truth is, the city is loaded with typical Italian charm. While the tower is certainly the most obvious highlight, Pisa itself boasts a very relaxed and calm atmosphere. It’s a great destination to take it easy and go with the flow, in true Italian style.
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