Italy is one of the most popular destinations for American tourists and, whether you’ve been once, twelve times or not at all, there’s always somewhere new to see in the boot-shaped country.
I studied in Siena, Italy while in college and it was my first experience living with a host family. They welcomed me into their home and into their family, so this place will always hold a special part of my heart. The medieval town of Siena is right in the heart of Tuscany. The rolling hills, the wine, the food… for me, this region is Italy.
Another quaint Tuscan town I love is Lucca. Famous for its city walls that completely encircle the town, it’s also relatively hill-free (a rarity in Tuscany), so bike rides are very popular. One of my favorite parts is the Piazza dell’Anfiteatro, which is a public square that was the base of a former amphitheater that once housed up to 10,000 spectators.
Another less-famous nearby village is Radda in Chianti, right in the heart of the Tuscan vineyards. This tiny little village is barely accessible by car (it takes lots of bumpy, dirt roads to get there), but totally worth it when you arrive. We enjoyed an Aperol Spritz and (of course) a glass of Chianti as we watched the sun go down over the surrounding hills.
Pisa is obviously well-known for its Leaning Tower – and it’s also a very affordable Ryan Air hub for the region. It can be a bit gritty, but we found our most recent visit, where we explored the less touristy areas of the city to be very enjoyable. We had delicious gelato, to boot.
One of my very, very favorite small Tuscan towns is San Gimignano, a small, medieval town with plenty of towers and arguably the best gelato in the country. Nicknamed the “Manhattan of Italy” for its preservation of 14 of its medieval “tower houses” — some of which you can climb to see the views of the rolling hills.
Finally, you can’t talk about Tuscany without at least mentioning its largest and most famous city: Florence (Firenze). It’s a must-see in Italy but, truth be told, I like to get out quickly for more time to explore the true heart of Tuscany: its rolling hills and smaller villages. Florence has world-class museums and history, but it is always crawling with a bit too many tourists for my taste.
And, as Giuseppe Verdi famously said, “you may have the universe if I may have Italy.”
