Day 1: Arrival in Pisa and Explore
Pisa is often the starting point for Tuscan road trips, especially since it has an international airport. So whether you’re arriving by plane or driving in from a nearby country, let’s kick off our Tuscan adventure with Pisa!
Morning: Start your day with the must-visit Leaning Tower of Pisa in the Piazza dei Miracoli (Square of Miracles). This UNESCO World Heritage Site isn’t just about the tower—the square also includes the impressive Cathedral of Santa Maria Assunta, the round, marble-clad Baptistery, and the Camposanto Monumentale, a beautiful cemetery said to contain soil from Jerusalem. Snap your obligatory cheesy tower photos (we know you want to!) and continue a stroll through Pisa. If you are hungry you can grab food here: I Porci Comodi.
Afternoon: After capturing the perfect tourist shot with the Leaning Tower, explore the Natural Park Migliarino San Rossore. This beautiful park, stretching to the sea, is a local favourite for morning runs and horseback rides. It’s also a haven for wildlife—keep an eye out for the friendly animals like wild dear, foxes, rabbits, who aren’t shy around people!
Where to Eat in Pisa:
Evening: Drive to Lucca (about 30 minutes) and settle in for the night.
Where to Eat in Lucca: pick any restaurant at Piazza dell’Anfiteatro where you can enjoy a georgeus view, but here are a few recommendations:
Day 2: Day 2: Discover Lucca and Drive to Florence
Morning: Start your day by exploring Lucca’s well-preserved Renaissance walls. Walk or run, whichever you prefer, along these ancient walls and enjoy the stunning views of the city below. Don’t miss a visit to Piazza dell’Anfiteatro (where we had dinner yesterday), uniquely shaped like a Roman amphitheater.
You can grab a panini at Ciacco.
Afternoon: After lunch, continue to Florence (about a 1.5-hour drive). Arrive in Florence and take some time to relax before heading out to explore the city.
Evening: Enjoy a meal with a view of the Duomo or in one of Florence’s lively piazzas.
Where to Eat in Florence:
Day 3: Florence Highlights
Morning: Florence is a city that feels like an open-air museum, so prepare comfortable shoes! Begin your day by visiting the Cathedral of Santa Maria del Fiore (Duomo). Climb to the Dome for a breathtaking view of the city. This is one of Florence’s most iconic landmarks, so make sure to give yourself plenty of time to take it all in.
Where to grab a quick bite or refreshment in Florence:
Afternoon: After lunch, explore Piazza della Signoria, Palazzo Vecchio, and the historic Ponte Vecchio. Each of these sites offers a glimpse into Florence’s rich history, you’ve all heard about Medici’s! For more tips on how to make the most of your time in Florence, visit Top Things to do in Florence.
Evening: Head to Piazzale Michelangelo for a stunning sunset view over Florence. This is a perfect spot to relax and just enjoy the view.
Day 4: Art and Culture in Florence
Morning: Spend the morning at the Uffizi Gallery, home to masterpieces by Botticelli, Leonardo da Vinci, and Michelangelo. Art lovers will find themselves in paradise here, or even if you are not a art fan, you just can’t miss this! It is outstanding what have peple created hundreds of years ago.
Afternoon: Visit the Galleria dell’Accademia to see Michelangelo’s iconic David statue. This museum also houses other important works of art, making it a must-see in Florence.
Evening: Relax in the Boboli Gardens, a beautiful green space filled with statues, fountains, and stunning views of the city.
Day 5: San Gimignano and Monteriggioni
Morning: Drive to San Gimignano (about 1.5 hours) and explore the “City of Beautiful Towers.” This medieval town is famous for its tall towers. While you’re there, don’t miss out on a visit to Boboli1909 for what might be the best panini you’ll ever have!
Where to Eat in San Gimignano:
Afternoon: Drive to Monteriggioni (about 30 minutes) and walk the ancient walls. Monteriggioni is a small but charming medieval fortress town, perfect for a quick stop on your way to Siena.
Evening: Arrive in Siena (about 20 minutes drive) and enjoy dinner in the city.
Where to Eat in Siena:
Day 6: Siena and Montalcino
Morning: Start your day in Siena by exploring Piazza del Campo and the Siena Cathedral. The city’s medieval architecture and rich history make it a must-visit in Tuscany.
Grab breakfast or snack at II Bocconcino, they have, hands down, the best panini! If you want something sweet, at Pasticceria Nannini Conca D’Oro try traditional Siena cookies.
Afternoon: After lunch, drive to Montalcino (about 1 hour) and enjoy a wine tasting of the world-renowned Brunello di Montalcino. Montalcino is not only famous for its wine but also for its charming atmosphere and beautiful views of the surrounding countryside.
Evening: Stay overnight in Montalcino or nearby to fully enjoy the peaceful atmosphere of the Tuscan countryside.
Day 7: Pienza, San Quirico d’Orcia, and Val d’Orcia
Morning: Drive to Pienza (about 40 minutes), the “perfect postcard town” of Tuscany. Explore the town, visit a pecorino cheese farm, and take in the breathtaking views of the Val d’Orcia.
Pienza: Dairy Farm Tour with Pecorino Cheese Tasting
Visit a dairy farm in the hills of Val d’Orcia to observe the techniques of cheesemaking.
Book NowWhere to Eat in Pienza:: Enjoy lunch at Trattoria Latte di Luna in Pienza—highly recommended for its delicious, authentic Tuscan cuisine! We ate there at least 4 times and we always return! The family working there is so kind and welcoming, just visit them and thank us later.
Afternoon: Visit San Quirico d’Orcia and explore Horti Leonini, a bautifull Renaissance garden. Afterward, drive through the iconic Val d’Orcia to Montepulciano (about 30 minutes) and explore the town’s film locations and stunning views. If you want to explore more of Val d’Orcia, check our blog Top Things to Do in Val d’Orcia.
Evening: Settle in for the night in Montepulciano or nearby to conclude your Tuscan adventure. We have an amazing accommodation to recommend:
Sleep in a castle in the heart of Tuscany
Spend the night in a real 12th-century castle and wake up surrounded by history, charm, and countryside views.
Book NowIf you have more time and want to explore more (which we know you do—you’re in Tuscany, after all!), be sure to check out our other blogs:
- The Ultimate Tuscany Road Trip Guide
- Tuscany’s Hidden Gems: Best Photo Spots for Photographers
- Top Things to Do in Val d’Orcia
We hope you enjoyed our 7-day itinerary for Tuscany! Feel free to shorten it or, even better, stay longer if you can—trust us, once you’re here, you’ll never want to leave. Tuscany is a place we return to every year, and we’ve packed this guide with all the tips and info we think will help you. Happy travels, and don’t be surprised if you start planning your next visit before you’ve even unpacked (as I’m writing this I’m already planning Tuscany for the 5th 6th time)!