How to Spend 3 Days in Tuscany

With three days to explore Tuscany, you’ll be able to savor picture-perfect hill towns, scenic vineyards, and world-class art and architecture while also visiting the iconic Leaning Tower of Pisa. Here’s how to make the most of three days in Tuscany. 

Day 1: Siena, the Crete Senesi, and the Val d’Orcia

Begin by visiting one of the most beautifully intact historic towns in Tuscany: Siena. With a historic center rich in architectural masterpieces and views across the rolling landscape of Crete Senesi and the woodlands of Val d’Orcia, Siena offers both culture and scenery. Start the day with a skip-the-line tour of the city’s exquisite Gothic cathedral to admire works by Donatello, Michelangelo, and Bernini before moving on to the crypt, baptistry, museum, and Piccolomini Library. Then take a deep dive into the city’s medieval center with a tour of the Piazza del Campo, home to the Palazzo Pubblico and Torre del Mangia, and the Basilica di San Domenico. 

In the afternoon, strike out through the surrounding countryside by vintage Fiat 500, bike, or horseback to savor some of the most unforgettable vistas in Tuscany and stop at picturesque towns like Pienza, Montepulciano, and Montalcino.

Day 2: Chianti and San Gimignano

Head to Tuscany’s Chianti countryside and take a driving or Vespa tour through the sleepy hilltowns of Greve in Chianti, Panzano, Radda in Chianti, and Castellina in Chianti. In the afternoon, focus on the region’s beloved cuisine: Wine tours by car, bike, or horseback are all great options for exploring the vineyard-covered hills dotted with tiny cellars where you can sample some of the area’s best wines. This is also an ideal area to join a hands-on cooking class in the countryside and learn to prepare classic Tuscan dishes.

From Chianti, continue on to San Gimignano to take in its delightful medieval old town in the quieter hours of the evening. Tour highlights like the city’s 14 historic towers, the Collegiate Church of Santa Maria Assunta, and Piazza Duomo on foot before tucking into a Tuscan dinner.

Day 3: Pisa and Lucca

On your final day, make your way to one of Tuscany’s headliners: the Leaning Tower of Pisa. Topping Italy’s list of highlights, this bell tower can be uncomfortably crowded in the morning, so begin your day with a guided tour of Pisa’s historic center on foot or via Segway or bike. In the afternoon, join a tour that includes skip-the-line tickets to take in the spectacular UNESCO-listed Piazza dei Miracoli. Follow your guide through the gothic Duomo and adjacent baptistry, the Leaning Tower, the Opera del Duomo Museum, and the Camposanto cemetery to fully appreciate these architectural masterpieces. 

End your three days in the exquisite (and much less crowded) town of Lucca. Take a walking or biking tour of the highlights in the historic center before capping off the day with an evening “passeggiata” (stroll) along Via Fillungo.