Consider the old town of Siena as an open-air museum centered around the Piazza del Campo and Siena Cathedral (Duomo di Siena), a Gothic masterpiece and one of Siena’s most impressive sights. The historic center, a UNESCO World Heritage Site, is compact and easily visited in a few hours. Put the city’s important urban landmarks, such as the Palazzo Pubblico and Torre del Mangia, into context by joining a small-group or private walking, bike, or Segway tour. Many tours offer a skip-the-line entrance to the Duomo to maximize your time. And, some guided tours include a stop at the Contrada Museum to learn about Siena’s famed Palio horse race, as well as a gelato break.

Set deep in the Tuscan hills, Siena is the perfect spot to discover this region’s traditional cuisine. Spend your afternoon taking a food tour in the city center that samples some of the area’s best cheeses and salami, local truffles, and the city’s famed panforte and ricciarelli sweets. Oenophiles can opt for a wine tour to learn about the prestigious varietals produced in the vineyards of nearby Chianti, and those who want a more hands-on experience can join an informal cooking class to learn how to prepare Tuscan classics.

The beauty of Siena’s historic center is matched by that of the surrounding rolling landscape, perhaps most striking at dusk. As the setting sun casts a golden light over the countryside, strike out for a scenic driving tour through the vineyard-covered hills of Chianti, with stops for wine tastings and dinner at a tiny hilltop village. Alternatively, saddle up and explore the environs on horseback, an option if traveling with older kids and an unforgettable way to top off your day of culture and cuisine in Siena.