Begin your day by getting to know the Siena Cathedral (Duomo di Siena) from top to bottom. Beat the crowds by booking skip-the-line tickets so you don’t have to wait to enter the complex and can take your time exploring the Gothic church, crypt, baptistry, museum, and Piccolomini Library.

From Siena’s soaring cathedral, move on to its medieval historic center, centered around the Piazza del Campo. Join a private walking tour to take in all the town highlights in just a few hours, from the imposing Palazzo Pubblico and Torre del Mangia to the cobbled lanes lined with shops.

After a day of art and architecture, it’s time to unwind with an evening of food and wine. An informal cooking class or wine tasting workshop offers a hands-on way to learn about—and sample—Tuscany’s regional cuisine and cap off your first day in Siena.

You’ve seen the sights in town, now head for the hills. Join a wine-tasting day trip to Montalcino or San Gimignano, or travel by Vespa scooter or vintage Fiat 500 to the wineries just outside Siena. Outdoor enthusiasts can join a hiking or e-bike wine tour with tastings and lunch.

Siena is famous for its prestigious wine, traditional crafts, and fairytale scenery. You’ve crossed wine off the list, so devote the afternoon to learning the history of majolica production with a ceramics workshop, or join a guided photography tour to capture choice shots of the town and its views.

Make your final evening memorable by watching the sun set over the medieval old town and rolling countryside beyond. Head to the panoramic Piazza del Mercato with a night tour, or climb to the top of the Torre del Mangia for sweeping views across the Sienese hills.