Your Ultimate Guide to Getting from San Gimignano to Florence

Traveling from San Gimignano to Florence is one of the most rewarding routes in Tuscany, blending medieval charm with Renaissance elegance. In just under 1.5 hours, you can go from strolling cobbled lanes lined with towers to exploring iconic landmarks like the Duomo and Ponte Vecchio. The journey is easy to plan by car, bus, or private transfer, with flexible options depending on your pace. Along the way, consider adding a stop at one of the many wineries offering Tuscany wine tours, the rolling vineyards between San Gimignano and Florence are home to some of the region’s most celebrated wines, making this short trip a feast for the senses.

Best things to do from San Gimignano to Florence

Wander through the historic center of San Gimignano

The town of San Gimignano stands as one of Tuscany’s most iconic medieval gems. Wandering through its UNESCO-listed historic center feels like stepping into a living museum. Towering stone spires, once symbols of family power, line the skyline, while cobbled alleys lead you past artisan boutiques and quiet courtyards. At the heart of it all lies Piazza della Cisterna, a sun-drenched square filled with gelato shops, leather artisans, and the timeless rhythm of Italian village life.

Climb before leaving

Kick off your San Gimignano to Florence adventure with a climb up Torre Grossa, the tallest tower in town. From the top, you’ll get sweeping views over vineyards, olive groves, and cypress-lined hills, a postcard-perfect start to the day. On your way back down, step inside the Palazzo Comunale to explore the Civic Museum, where centuries-old frescoes and local artifacts bring Tuscany’s medieval history to life.

How to get from San Gimignano to Florence

Getting from San Gimignano to Florence is simple with a bit of planning. While there’s no direct train line from San Gimignano, you can hop on a local bus to Poggibonsi (about 25 minutes), then catch a regional train straight to Firenze Santa Maria Novella. The total journey takes around 1.5 to 2 hours. Prefer more freedom? Renting a car lets you explore the Tuscan countryside at your own pace, with the added bonus of stopping at local wineries along the way. Private transfers and guided tours are also available for those looking for a stress-free experience.

Explore Monteriggioni’s medieval walls

A quick detour from the main route brings you to Monteriggioni, one of Tuscany’s best-preserved medieval gems. Encircled by striking 13th-century stone walls and towers, this hilltop village feels frozen in time. Wander along the ancient ramparts, step inside the simple yet charming Romanesque church, and enjoy an espresso in the tranquil central piazza. It’s a serene, scenic pause that adds a touch of old-world magic to your journey from San Gimignano to Florence.

Dive into the Renaissance in Florence

As you reach Florence, the landscape shifts from hilltop serenity to Renaissance grandeur. Start with a stroll to the Florence Cathedral and Brunelleschi’s dome, then dive into the Uffizi or the Accademia for world-class art. Florence wine tours also await, from historic enotecas to stylish wine bars, you’ll find Tuscan tasting experiences right in the city center, many just steps from the Duomo.

Looking for unforgettable moments? Here are the best things to do Florence, all within walking distance.

Catch the sunset from Piazzale Michelangelo

Cap your journey with a view. Cross the Arno River to Piazzale Michelangelo, where Florence unfolds beneath you in all its glory. As the sun dips low, golden domes, stone bridges, and terracotta rooftops glow in the fading light, the perfect finale to a day that began among medieval towers and Tuscan vines.

Sip wine with a view over the Ponte Vecchio

Firstglass is a fresh take on wine tasting, right in the beating heart of Florence. It offers single-glass 100 ml pours (no need to share a full bottle), served in front of the Ponte Vecchio, so you’re sipping with one of the city’s best views. The tasting lasts about an hour, ideal if you’re fitting wine in between museums or before dinner. It’s approachable, elegant, and just the right amount of indulgence for a day in Florence.

San Gimignano to Florence: What to do outside the city?

Escape to Fiesole

Just 5 miles from Florence, the charming town of Fiesole offers a peaceful contrast to the bustling Renaissance capital. Perched on a hill overlooking the Arno Valley, it’s the perfect half-day escape for panoramic views, Roman ruins, and elegant villas. You can reach Fiesole in just 20 minutes by bus from Florence’s city center. Once there, stroll through its archaeological site with a Roman amphitheater, visit the 14th-century cathedral, or enjoy an espresso with sweeping vistas. It’s a relaxing stop that lets you experience Tuscany’s quieter side, without straying far from Florence.

Explore the vineyards of Chianti Classico

Just a short drive from San Gimignano toward Florence, the Chianti region delivers everything you’d expect from the Tuscan countryside, rolling hills, stone villas, and rows of vineyards stretching toward the horizon. Planning a scenic journey from San Gimignano to Florence? Make time for a stop in Chianti. Known for its world-famous wines and postcard-perfect landscapes, the area is ideal for private wine tastings with lunch, guided cellar tours, or a visit to a historic villa. Some wineries near San Gimignano are reachable by local bus, but renting a car gives you more freedom to explore. Try local truffle dishes, aged pecorino, and of course, a glass of Chianti Classico, all while soaking in sweeping views of olive groves and sunlit vineyards.

Visit Siena’s timeless streets

Siena is one of the most charming and historic cities in Tuscany, only about 50 minutes south of San Gimignano. You can take the bus or drive in around an hour to reach its UNESCO-listed historic center. Known for its large shell-shaped piazza, Piazza del Campo, and its stunning Duomo, Siena makes for a perfect day trip from Florence. You may even want to start your Florence to Siena itinerary with a detour to explore both Siena and Pisa before heading north. For those relying on public transport, check the schedule for the bus from Florence or board the train from Florence to Poggibonsi and then connect to Siena.

While you’re there, explore the heart of Tuscany through curated Siena wine tours, offering tastings in historic estates and sweeping vineyard views.

Good to know before your trip from San Gimignano to Florence