Itineraries for Your Trip to Siena
3 Days in Siena for First Timers
There is no better base to explore Tuscany than Siena, the UNESCO-listed medieval gem that sits within striking distance of three iconic Tuscan landscapes—Chianti, the Val d’Orcia, and the Crete Senesi. Siena’s old town is one of the best-preserved in Italy, with a soaring Gothic cathedral, maze of winding shop-lined lanes, and a sweeping central square that hosts the historic Palio horse race each summer.
It was this raucous race that first drew me to Siena as a fresh-faced backpacker, but I have discovered the town’s quieter charms during my countless subsequent visits. Take in the best of Siena and its surrounding hills in three days with these tips.
The summer sun can be relentless in Siena, especially in its largely shadeless Piazza del Campo. Protect yourself with a hat and sunblock.
If you only have time for one thing, make it the magnificent Duomo, where you can admire works by Donatello, Michelangelo, and Bernini.
Spend today exploring Siena’s rich culture and history, starting with the soaring Gothic Duomo. Head out early in the morning to 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 tour that includes architectural treasures such as the Piazza del Campo, Palazzo Pubblico, Torre del Mangia, and Basilica of San Domenico.
The lunar landscape of the Crete Senesi extends out from Siena’s hilltop perch, offering some of the most dramatic scenery in Tuscany. Admire these rolling hills from above with a sunrise hot air balloon ride this morning. Drift over terra cotta-hued fields, then toast to your flight with a prosecco breakfast once you’ve landed.
Now that you’ve marveled at the Crete Senesi from the air, explore the unique countryside by land with a hike, horseback excursion, or ATV adventure. Wine enthusiasts can break up the day with a stop at one of the area’s many cellars for a tour and tasting.
Siena sits just outside the southern border of Chianti, making it an ideal jumping-off point for a day of village-hopping. Take a scenic drive, hike, or bike ride between hilltop gems like Greve, Castellina, and Radda, with a break at a local farm or winery for a Tuscan lunch.
Alternatively, turn your sights south to the UNESCO-listed Val d’Orcia. Explore the Renaissance hill town of Pienza, and the Montepulciano, and Montalcino wine countries for a day of spectacular architecture, scenery, and food.
