Visiting the Tuscany Countryside: A 3-Day Road Trip Guide

Visiting Tuscany for just a few days takes a lot of planning, considering the many sights, natural beauties, and landmarks that are regarded as staples for every visitor. Imposing churches, impressive Renaissance architecture, tiny hillside cities, massive sunflower fields and cypress-lined roads, and Medieval remains reminding the rich history of Tuscany, definitely make choosing an itinerary or road trip a challenge. Indeed, there is something special about each town and each different location in the Tuscany region, be it the countryside or the coastline.

To give you a helping hand, we suggest a 3-day road trip that will tick most of your boxes and enable you to view the unbelievable charms and delights of this adorable part of Italy.  

Florence during a road trip

Day 1: Glorious Florence 

No trip to Tuscany can ever be complete without a stop to enchanting Florence, which is, rightfully, regarded as a prominent cultural hub. Indeed, some of the most recognisable art of all time is found in Florence (I.e., the Birth of Venus and the statue of David).  

Sights such as Il Duomo (the Cathedral), the Uffizi Gallery (home to infamous works by Michelangelo, Da Vinci, Botticelli, and others), the Tower of Palazzo Vecchio, the Ponte Vecchio bridge, Piazzale Michelangelo, Palazzo Vecchio, and the Accademia (houses David of Michelangelo – the world-famous statue) are quintessential additions to any Florence trip. 

And, while strolling through the bewildering Renaissance capital, do consider treating yourself with a delicious gelato or the juicy T-Bone steak known as Bristecca alla Florentina! And, don’t forget that the absolutely ravishing Lake Trasimeno (Lago Trasimeno) is just a short drive from Florence, bordering with Umbria. It’s not only the 4th largest lake in Italy, but also a marvellous natural spectacle full of well-trodden trails, magnificent beauty, and an inviting splash of inky blue against a green background. 

Tip: Staying on the border to Umbria will allow you to have easy access to both Umbria and Tuscany. Here are some of the most stylish Florence luxury rentals to accommodate your needs.  

Assisi Road Trip
Photo by Lachlan Gowen on Unsplash

Day #2: The Medieval Town of Assisi  

Less than a couple of hours from Florence lies one of the most stunning towns in the Tuscany region. Expect to be greeted by huge white walls created to fortify Assisi from invaders back in the Middle Ages, stone alleys, rolling sunflower fields, and a large number of churches and convents with precious religious items and captivating architecture.  

As for the must-stops here, the Basilica of San Francesco d’Assisi is an elegant Papal minor basilica and a significant pilgrimage site not to be missed. Just make sure to have your shoulders and knees covered when entering the basilica, like in all other Italian churches.  

To end the day, you could climb up to Rocca Maggiore, a hill-high fortress, and take in staggering views over the cascading valleys spreading below your feet. This can be before or after you visit one of the popular local wineries and pamper your taste buds with some of the best wines in Italy.  

Let us suggest some lovely properties to stay near Assisi.  

Montepulciano road trip
Photo by Stanley Kustamin on Unsplash

Day #3: Montepulciano  

Within 2-3 hours, you reach Montepulciano after an admittedly scenic drive that grants views including endless fields of vineyards and cypress trees. The name may ring a bell, as this region produces the best Montepulciano wines. Despite its small size, Montepulciano has a lot to offer – from amazing panoramas of the flourishing countryside to a lovely maze of side streets, each hiding a secret treasure to be discovered.

When the time comes for the much-anticipated wine-tasting adventure, you may want to combine the experience with dinner or lunch. That way, you’ll be able to share a romantic time with your loved one or friends and nibble on local delights. In this case, though, ensure you make a reservation or show up before 8pm when the Italians have dinner to avoid the large crowds.  

Feel free to explore these fabulous farmhouses and chic cottages for your overnight stay.  

Yes, chances are you will feel that 3 days is merely enough time to soak up Tuscany’s unsurpassable charms. But, it’s a start! Truth be told, Tuscany will never cease to amaze you,  no matter how many times you have visited it!

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