Itineraries for Your Trip to Siena
2 Days in Siena for First Timers
Siena has long been my favorite base when visiting Tuscany, with its vibrant hilltop old town and ideal location for dipping into the medieval villages and scenic valleys scattered through the outlying countryside. Its UNESCO-listed historic center is a medieval set piece with a spectacular cathedral, a perfectly preserved main square, and endless opportunities for shopping and dining. Just outside of town, the hills of Chianti, the Val d’Orcia, and Crete Senesi offer scenic backdrops for day trips and wine tours.
I first visited Siena decades ago on a backpacking trip through Italy, drawn by guidebook descriptions of its annual Palio festival and easy train connection from Florence. In the years following that introduction, I’ve been able to experience the city outside of its festival revelry to take in its authentic small-town vibe. Here’s how to plan two days in Siena for the first time.
Most sightseeing in Siena and its environs is outdoors under the unforgiving Tuscan sun, so pack protective sunscreen and a hat.
If you only have time for one thing, make it a stroll through Piazza del Campo, one of the most unique squares in Italy.
Siena’s Duomo is more than just an exquisite Gothic cathedral; it's an entire complex that merits a morning’s attention. Begin here while the bus tour crowds are focused on the rest of the old town, with skip-the-line tickets to the Gothic church with its crypt and baptistery, plus the adjacent museum and Piccolomini Library. Admire works by Michelangelo, Donatello, and Bernini as you take your time inside.
After lunch, take in the highlights and hidden gems of one of Italy’s most intact medieval cityscapes with a walking tour of Siena’s historic center. Learn about the history and lore of Piazza del Campo, lined by gems such as Palazzo Pubblico and Mangia Tower; plus, visit the Basilica of San Domenico and Santa Maria della Scala. You can cover the headliners in just a few hours, leaving time to explore the Civic Museum and National Art Museum on your own.
Cap off your day by savoring the flavors of Tuscany with a food-focused evening. Siena sits at the crossroads of the region’s top culinary areas, and the town’s culinary scene is second to none. Grab a table at one of the restaurants lining Piazza del Campo for dinner with a view or unveil the secrets to preparing some of Siena’s most beloved dishes with a cooking class and dinner at a local home.
Strike out beyond Siena’s city walls to explore Chianti this morning, which unfurls across the hills north of Siena. Village hop between Radda, Greve, and Castellina in Chianti with a scenic hike or an e-bike tour, or sit back and take in the views with a driving tour. End at a local winery around midday for a guided visit and tasting.
Head west this afternoon to San Gimignano, famous for its medieval towers jutting into the sky above the old town. Compact and easy to cover in just a couple of hours, this charming spot is quieter in the afternoon when many of the bus tours have left. See the highlights with a walking tour, then cool off with gelato at the award-winning Gelateria Dondoli.
The return drive from San Gimignano to Siena takes you directly past Monteriggione, one of the most charming walled hamlets in all of Tuscany. Stop here to enjoy your final stroll of the day before continuing on to Siena for an evening wine tasting. The wine-producing areas of Chianti, Val d’Orcia, and the Sienese hills stretch out on all sides, making the town a premium destination for wine lovers.
