Discovering Tuscany from Rome to Florence

Recently, I had the privilege of escorting a group of my awesome clients on a curated adventure from Amalfi through the Eternal City of Rome and the serene beauty of Tuscany, concluding in the Renaissance city of Florence. If you missed the previous 2 blogs about the Amalfi Coast and Rome, click on the hyperlinks  👈🏻.

After our time in Rome, we headed out into the countryside toward Tuscany. Tuscany is famous for its tall Cypress trees and delicious wines like Vino Nobile di Montepulciano and Brunello di Montalcino.

Our first stop was Pienza, a charming little town in Val d’Orcia known for its picturesque Cypress tree-lined streets and amazing pecorino cheese. We had the chance to visit a local cheese maker and sample a range of freshly made cheeses. Tasting the freshly made pecorino cheese in the heart of Pienza was an authentic experience that really let us savor the flavors of the region.

After visiting Pienza, we headed to Montepulciano and ended up exploring a really cool underground winery. Going down into the cellar was such an awesome experience, and we learned so much about how Tuscan wine is made. The wine tasting was just average, though, but it allowed us to try out some of the local wines from Montepulciano.

Castel Monastero was originally a medieval monastery dating back to the 11th century, later transformed into a luxurious retreat that still preserves its historic charm and rich cultural heritage. This was our home for our three-night stay, with beautiful views of the surrounding vineyards and olive groves.

After that, we spent some time exploring the medieval walled cities of Siena and San Gimignano. Siena is famous for its beautiful medieval architecture, especially the iconic Duomo di Siena cathedral with its unique black and white striped façade.

There is also the Palio horse race in Siena! It’s a really cool tradition that’s been going on for centuries. They hold it twice a year in the Piazza del Campo, and all the historic neighborhoods, called “contrade,” compete against each other.

San Gimignano is often referred to as “Medieval Manhattan” due to its impressive skyline of historic towers. Of the original 72 towers, 14 are still standing today. You’ll get one of the most impressive views of Tuscany from the city walls.

We finished our time in Tuscany with an amazing lunch at an exquisite winery in Chianti before heading to Florence. Florence is known as the birthplace of the Renaissance and has some incredible art and architecture from that time. The Duomo is just stunning with its famous dome by Brunelleschi, and the Uffizi Gallery has some breathtaking paintings by Botticelli, Raphael, and Michelangelo. At the Accademia Gallery, we were awestruck by the magnificence of Michelangelo’s David. Florence is basically a gold mine of Renaissance masterpieces.

Florence is famous for its amazing food, deeply rooted in Tuscan tradition. We enjoyed classic Florentine dishes like the famous Bistecca alla Fiorentina (a thick, grilled T-bone steak), hand-crafted pasta (my favorite is cacio e pepe using pici pasta), and the region’s renowned Chianti wines.

Florence has always been a place where talented artisans thrive, known for their expertise in crafting leather goods, jewelry, ceramics, and textiles. If you have the chance, you should definitely check out the city’s old workshops and watch these master craftsmen at work. It’s pretty cool to see them using techniques that have been handed down for generations.

As we were wrapping up our trip, two couples headed to Venice while the rest of us started our journey back to the United States. We all felt a bit nostalgic for our trip as soon as we left.

This adventure was a testament to the elegance of travel—a harmonious blend of discovery, culture, and gastronomy. Crafting such bespoke adventures for my valued clients is very rewarding. Until next time, keep exploring, savoring, and cherishing the joy of travel!  And click here to start your next getaway with us!