Siena is more than just a postcard-perfect medieval hilltown. The UNESCO-listed gem is also the ideal base for exploring Chianti, the Val d’Orcia, and the Crete Senesi—a quintessential Tuscan landscapes dotted with tiny villages and rolling vineyards. Here are a few ways to take in Siena and the surrounding countryside in three days.
Day 1: Explore the Town
Delve into the rich culture and history of this time-capsule town by devoting the day to exploring Siena’s delights, large and small. Begin your visit with skip-the-line access to the soaring Gothic Siena Duomo. Early morning tickets leave you time to linger in the magnificent church and savor works by Donatello, Michelangelo, and Bernini (and help you avoid the tour-bus crowds that flock to the complex later in the day).
Afterwards, get to know the medieval center of the city with a walking or Segway tour that touches on its architectural treasures, such as the Piazza del Campo, Palazzo Pubblico, Mangia Tower (Torre del Mangia), and Basilica of San Domenico. Some tours also provide insight into the town’s famous Palio festival with a stroll through the contrade districts, and most pause in the Piazza del Mercato for photo ops from the scenic overlook and a chance to explore the quiet artisan-lined back streets.
Day 2: Outside the Walls
Located just outside Siena’s imposing medieval city walls, the undulating Crete Senesi region offers some of the most striking views in Tuscany. Admire this landscape from the air on a hot-air balloon flight or from the ground with a guided hike through the hills. Foodies can combine countryside and cuisine by joining a truffle hunt or a cooking class, and wine lovers can visit the local wineries on a tuk-tuk, all-terrain vehicle, or e-bike winery tour.
True oenophiles may want to head a bit further afield to sample prestigious Chianti or Brunello di Montalcino wines where they are produced. Opt for a day trip that provides transportation, and you can imbibe with peace of mind. Most wine-tasting tours include stops at a winery or two for tastings as well as free time in the scenic hill towns like Radda, Castellina, or Montalcino and an informal Tuscan lunch.
Day 3: Adventures Across the Border
After exploring the city and its surroundings, take advantage of Siena’s strategic location in the center of Tuscany, and take a day trip to the furthest reaches of the region—or even across the border into Umbria, Liguria, or Emilia-Romagna. Unforgettable Tuscan destinations include the hill towns of San Gimignano, Volterra, and Montepulciano and the scenic streets of Pienza.
You can also make a break for the Ligurian coast with a guided tour of the fishing villages of Porto Venere and the Cinque Terre and or double-down on art and culture by taking in the frescoed museums and churches of Cortona and Assisi, located on the border between Tuscany and Umbria. Alternatively, you can rev your engines with a guided tour of the Ferrari Museum near Modena and enjoy tastings of local balsamic vinegar and Parmigiano-Reggiano cheese. Then head back to Siena for one last night enjoying the city’s enotecas and wine bars.