Spanning the Apennines to the Tyrrhenian sea, Tuscany is home to some of Italy’s finest landscapes and artistic legacy and is an excellent place to enjoy exceptional natural beauty along with incredible cultural sites. There are so many treasures to the region it can be difficult to decide where to base yourself. Whether you prefer culinary delights or art history, here’s a primer to top cities in Tuscany to soak up the best of Italian culture while staying at an exquisite luxury villa nearby.

Photo by Venkat Raman / Flickr


While it enjoys world-wide notoriety for its Leaning Tower, Pisa has more to offer. With the city center about 5 kilometers from the Pisa airport, Pisa makes for a perfect jumping off point to explore Tuscany. Start your day in Piazza dei Miracoli. Home to the Leaning Tower (already leaning when completed in 1372), this UNESCO World Heritage site represents the three major stages of human life: the Baptistry (representing birth), the Romanesque Cathedral of Santa Maria Assunta (representing life), and the cemetery (representing death). Getting hungry? Take a detour to a local restaurant to try cecina. This flat bread is gluten free, and made from a base of chickpea flour, oil, salt, and pepper.

Lucca. Photo Credit: Ștefan Jurcă / Flickr


Situated on a flat plane at the foot of the Apuan Alps, Lucca makes for a mobility-accessible stop without sacrificing charming mountain views. Lucca’s Roman heritage reveals itself in the shape of the Piazza dell’Anfiteatro. This square is now a bustling square filled with local places to drink and dine, but its shape reveals its former use as a gladiatorial amphitheatre. Next, check out the archeological sites below the 12th century churches Saint Giovanni and Saint Reparata. Unlike other medieval cities such as Florence, Lucca maintained its ancient walls as the city expanded. Take in the view while enjoying a leisurely promenade along the parapets of the ancient city walls. Only 35 kilometers from the Pisa Airport, Lucca is easily accessible whether you’re touring multiple cities or just planning a getaway to enjoy Lucca and its surrounding countryside.

Santa Maria del Fiore, Florence by Mark Smith / Flickr


As Tuscany’s leading city, Florence offers visitors its breathtaking landscapes, renowned artworks, and the allure of Italian charm. As the birthplace of the Renaissance, Florence offers several options from the Uffizi to the Galleria dell Accademia to the Pitti Palace to soak up incredible artwork. Take a break from hanging out with Michelangelo’s David and stroll across the Ponte Vecchio to admire the Arno River. Stop for a coffee in Piazza della Signorina and try Cantucci, Florence’s almond biscotti. At just 11 kilometers from the Florence airport to the city center and with train links to all major Italian cities, Florence’s Roman roots to art by Da Vinci and Michelangelo are easy and accessible. Try to visit in spring or autumn to avoid the summertime heat and crowds. Piazza del Campo, by Philip Capper / Flickr


One of Tuscany’s most alluring medieval cities, Siena is situated across three hills. The heart of the city lies in Piazza del Campo, the site of the former Roman forum. Rebuilt between 1287 and 1355 during the reign of the Council of Nine, this red brick square features nine sections representing the Council, as well as symbolizing Madonna’s cloak, which is said to protect the city. Climbing the 500 steps to the top of the Torre del Mangia is worth it for a breathtaking view of the city and the surrounding landscape, while the adjoining Civic Museum offers some of Siena’s best artworks. The town also plays host to the bi-annual Palio horse race, a must-see recommendation of our experts at the Borgo Finocchieto, an exceptional luxury medieval hamlet rental located nearby Siena. For wine enthusiasts, Siena is also paradise. Pause in one of Siena’s wine cellars to taste the region’s Chianti Classico, Vernaccia di San Gimignano, Vino Nobile di Montepulciano, or Brunello di Montalcino. Equidistant from both the Pisa and Florence airports, Siena makes for an ideal base for exploring the various areas of Tuscany. 

Piazza di Arezzo. Photo Credit: Eduard Díaz i Puig / Flickr


Known for its goldsmiths and the backdrop of many films, Arezzo is one of Tuscany’s most affluent cities. Built by the Etruscans in the 9th century BC at the crossroads of four valleys, Arezzo later became one of a significant stop along the Roman Via Cassia. Though its medieval city center was destroyed during WWII, many of Arezzo’s churches and monuments remain. Don’t miss the Church of San Francesco, home to the remarkable early Renaissance fresco cycle by Piero della Francesca depicting the Legend of the True Cross. Next, visit the remains of the Roman amphitheater to bask in the city’s Roman roots. About an hour from the Florence, the oft-overlooked Arezzo should not be missed!



Pienza was declared an UNESCO World Heritage site in 1996, considered as the “touchstone of Renaissance Urbanism.” In 1469, Pope Pius II decided to shape Pienza as the ideal city: picturesque piazzas and artfully arranged streets, alongside elegant palaces and churches. Though he died before his concept could be fully realized, Pienza remains a perfect example of harmony between Renaissance construction and the breathtaking landscapes that make the Tuscan region so pleasant. Its warm, honey-toned buildings, surrounding vineyards, and specialty shops make the city one of rural Tuscany’s finest. Be sure to try Pienza’s Peccorino, a sheep’s milk cheese packing a sharp flavor perfect for grating over your pasta. No trip to Pienza could be complete without a visit to the stunning Val d’Orcia to the south of the city, one of the most beautiful natural settings in all of Tuscany. An hour and a half from Florence, Pienza makes for a delightful detour into the countryside.

Where to stay in Tuscany

Our local Tuscany villa experts represent the absolute finest luxury accommodation in the region whether you are looking for a medieval castle set on a vineyard with a divine pool or an elegant city apartment with views over the rooftops and rolling hills, reach out to one of specialists listed here to start designing your dream Tuscan vacation.