Itineraries for Your Trip to Tuscany
2 Days in Tuscany for First Timers
Tuscany is one of the most picture-perfect areas in Italy, with its iconic hills covered in vineyards and olive groves and topped by pocket-sized medieval villages. Most first-time visitors don’t realize how large the region is, however. This central Italian superstar stretches from the coastline far into the Apennines, encompassing dozens of historic towns and wine-growing areas.
On my first visit, I thought I could cover the entire region of Tuscany in just a few days—but I quickly realized that I had vastly underestimated its size. Over many return trips, I learned that it pays to focus on a few highlights to savor the history, views, and cuisine without feeling overwhelmed. Here’s how to plan two perfectly paced days in Tuscany on your first visit.
If you only have time for one thing, make it a walk through a postcard-ready hilltown in Chianti.
Tuscany is a four-season region, with hot summers, chilly winters, and wet stretches in between.
Chianti is the most famous—and some would argue the most scenic—area of Tuscany, home to rolling hills, historic vineyards, and groves of olive trees and truffle woods. Focus on this crowd-pleaser on your first day with a scenic Chianti sightseeing tour by car, Vespa scooter, or e-bike with stops in charming hill towns like Greve in Chianti, Panzano in Chianti, Radda in Chianti, and Castellina in Chianti.
Chianti is synonymous with its bold red wines, so you’ll want to taste them at the source while in Tuscany. This afternoon, sip the area’s iconic vintages with a wine tour or tasting that takes you to blockbuster landmark cellars or small boutique producers. You can opt for an experience that stops at just one or several Tuscan wineries.
End your first Tuscany day with some time exploring San Gimignano. This medieval hill town is one of the most atmospheric in Chianti but can get crowded during the day. Choose to visit in the evening after the bus-tour crowds depart to admire its 14 historic towers, Collegiate Church of Santa Maria Assunta, and Piazza Duomo. End with a Tuscan dinner at one of the town’s authentic trattorias.
Head west on your second day, beginning with a morning in Pisa. The Leaning Tower of Pisa is the headliner here, so you’ll want to visit this iconic sight along with the other highlights in Pisa’s Piazza dei Miracoli. Many tours also take in Pisa’s handsome historic center including, Knights’ Square (Piazza dei Cavalieri), and the Church of Santa Maria della Spina
After taking in the sights in Pisa, move on to Lucca. This historic walled town has a refreshingly authentic feel and relatively few tourists. Visit the Lucca Cathedral (Duomo di Lucca), Guinigi Tower (Torre Guinigi), and the Church of San Michele in Foro with a walking or biking tour through the old town, and end with a stroll along the top of the city’s medieval walls.
End your time in Tuscany by taking a deep dive into the region’s beloved cuisine. Join a cooking class in Lucca’s historic center or surrounding countryside to learn how to prepare classic dishes with a professional chef or home cook. Alternatively, relax over a home-cooked meal and savor a dining experience with local hosts.
