Day Trip to San Gimignano & Monteriggioni in Tuscany


Enjoy a day exploring the scenic countryside and picturesque villages north of Siena. Start with a leisurely walk around San Gimignano, a quintessentially Tuscan town comprised of medieval buildings perched atop one of the region’s iconic hills. Located in the Elsa Valley, San Gimignano is most famous for the 13th-century plazas, churches, and stone towers dominating the skyline. It's for these reasons that the entire town is a UNESCO World Heritage Site.

Walk along the ancient Via Francigena (the ancient pilgrimage road connecting to Rome). Your route will lead you through the town from Porta San Giovanni to Porta San Matteo, passing through Piazza della Cisterna, a grand square surrounded by the Palace of the Podestà, the Salvucci towers, and Piazza Duomo. Eventually, you'll reach the top of the town and enjoy amazing panoramic views from the Church of Saint Augustine.

You can also visit local craft shops and one of San Gimignano's famous gelaterias, which have rightly earned a reputation for producing some of the best gelato flavors in the world. Finally, climb the Torre Grossa and admire the amazing views across the vineyards and medieval city center.

The secret to a day trip to San Gimignano is arriving before or after the tour buses! San Gimignano is so much more than the one touristy main street, but most people don't have the time to really explore. 

After leaving San Gimignano, make your way to the impressive medieval fortress of Monteriggioni. The intact castle walls surround this town perched on a hillside and are a sight to behold! Take in the views, have a coffee, and enjoy wandering around the porticos and piazzas in the charming historic center.

Read more about unique and interesting experiences in Tuscany.

Itineraries with Day Trip to San Gimignano & Monteriggioni in Tuscany

Family Road Trip: Northern Lakes, Tuscany & Italian Riviera - 14 Days

Spend two weeks exploring northern Italy at your own speed with this self-drive itinerary that allows you to choose the stops. You'll start off in the northern lakes, with Lake Como and Lake Garda offering boat tours past villas and amusement parks alike. Then make your way into Tuscany, where you'll ride a horse-drawn wagon through the countryside and explore the medieval walled city of Siena and famous art of Florence. Finish your trip in the Italian Riviera and colorful five villages of Cinque Terre.

Explore Liguria & Tuscany: Cinque Terre, Florence, Pisa & Val D'Orcia - 13 Days

Explore Mediterranean beaches, Renaissance capitals, and medieval hill towns on this delightful 13-day tour through the Italian regions of Liguria and Tuscany. Start your adventure on the west coast, where you'll discover the quaint villages, rugged shorelines, and breathtaking scenery of the Cinque Terre. Head inland to spend a day wandering through history in Pisa, before journeying west to soak up the Renaissance splendor of Florence. The final five days take you deep into the Tuscan countryside, where you'll stay at a rural agriturismo villa and immerse yourself in the culture and landscape of the Val d'Orcia—wine tasting and truffle hunting around picturesque hill towns.

Highlights of Rome and Florence - 7 Days

Your trip to Rome and Florence starts with guided tours through Rome's historical core, Vatican City, and the Roman Forum, with walks through the Colosseum and to the top of Palatine Hill. Head to Florence to experience its historic squares, cathedrals, and museums, plus an Italian cooking class to learn how to make traditional pasta and dessert. End your trip in the Tuscan countryside with visits to Siena and San Gimignano, complete with walking tours and a wine tasting.

Explore Tuscany: Florence, Siena, & Montepulciano - 10 Days

This road trip around Tuscany is perfect for those looking to delve into Italian wine culture. Start in Florence, the birthplace of the Renaissance, stroll around its medieval plazas and cathedrals and see for yourself the history that permeates the city. Visit picturesque Tuscan villages and local wineries, getting a taste for local life and in some incredible surroundings.

Rome, Orvieto, Florence, & Verona - 14 Days

This route takes you through the highlights of Italy while exploring more of each region. Start in Rome, visiting the Vatican and Colosseum before making your way up to the lesser-known Umbria region for a stopover in Orvieto. Enjoy your time away from the big city and delight in the local life. Continue up to the birthplace of the Renaissance, Florence. This city's incredible plazas and cathedrals never disappoint. Finish off your trip in the Veneto region, staying in the lovely and romantic Verona and visiting its neighboring city, Venice.