How to Spend 2 Days in Tuscany

Land of jewel-like medieval towns, rolling vineyards, and a wealth of UNESCO-listed architectural sites, Tuscany is one of the most famous regions in the world. With two days, you’ll have time to dip into its charm before moving on its capital city of Florence or the rest of Italy. Here are your best options for spending two days in Tuscany.

Day 1: Chianti

**Morning:**If Tuscany is Italy’s most famous region, Chianti is its scenic crown jewel. Your first day, focus on this paradise of food, wine, and views. Start by joining a driving or Vespa tour along the scenic SS222, which passes some of the most picturesque hilltowns, like Greve in Chianti, Panzano in Chianti, Radda in Chianti, and Castellina in Chianti.

**Afternoon:**No jaunt through Chianti is complete without sampling the area’s food and wine. Visit some of the small family-run cellars hidden in the hills on a wine tour, or explore the wine country by horseback or on bike, stopping for tastings. Foodies can opt for a farmhouse cooking class to learn how to prepare classic Tuscan dishes.

**Night:**End your day in San Gimignano, a spectacularly preserved medieval hilltown that is particularly beautiful in the evening, after the bus-tour crowds depart. Stroll through the old town to take in its 14 soaring towers, Collegiate Church of Santa Maria Assunta, and Piazza Duomo, before relaxing over dinner at a local trattoria.

Day 2: Pisa and Lucca

**Morning:**The Leaning Tower of Pisa is on everyone’s must-see list, but resist the urge to head straight to the Duomo and its famous bell tower in the morning, when these popular attractions are overflowing with bus-tour crowds. Instead, join a guided walking, Segway, or bike tour of Pisa’s handsome historic center, the Piazza dei Cavalieri, and Santa Maria della Spina. 

**Afternoon:**Once the morning crowds have gone, head to Pisa’s famed cathedral complex on a guided tour that includes skip-the-line tickets. This glorious UNESCO World Heritage Site includes the gothic Duomo and baptistry, the iconic Leaning Tower, the Opera del Duomo Museum, and the Camposanto cemetery.

**Night:**From Pisa, continue on to Lucca, a lovely walled town that has a refreshing un-touristed feel. Take a walking or biking tour through the old town to visit the Duomo, Guinigi Tower, the Church of San Michele in Foro, and other highlights. End your two-day Tuscan adventure by joining the locals in the evening passeggiata (stroll) along Via Fillungo.