Day Trip from Rome to Tuscany by high speed train: Medieval Towns & Chianti Wine Tasting

Board a high-speed train at Rome Termini and, in just 90 minutes, you’re enveloped by the gentle curves of Tuscany’s vineyards. This carefully curated day trip from Rome to Tuscany lets you trade cobblestones of the Eternal City for medieval villages and world-renowned wines—all within a single, unforgettable day.

A Perfect Day Trip from Rome to Tuscany

Immerse yourself in Tuscany’s medieval charm and rolling vineyards on an all-by-train Rome to Tuscany day tour—no overnight stay required.

Morning in Monteriggioni: Start Your Day Trip to Tuscany from Rome

Step off the train and head straight to Monteriggioni, a jewel among Tuscan hill towns. Here, the perfectly preserved circular walls invite a leisurely stroll along ancient ramparts. From this vantage point, gaze across the Chianti hills where cypress trees punctuate fields of grapevines. The hushed atmosphere feels suspended in time, making it the ideal kickoff to your day trip from Rome to Tuscany.

Midday in Siena: Savor History on Your Rome to Tuscany day tour

Next, continue into Siena’s UNESCO-listed historic centre. Wander through narrow alleyways until you emerge in the shell-shaped Piazza del Campo, famed for its summer Palio horse races. Pause to admire the façade of the Palazzo Pubblico and its soaring Torre dei Mangia before sampling lunch in a nearby osteria—perhaps a hearty bowl of pici pasta with Tuscan ragù. This slice of medieval splendor is a highlight of any Day Trip to Tuscany from Rome.

Afternoon in San Gimignano: Medieval Towers on Your Day Trip from Rome to Tuscany

As the sun climbs higher, make your way to San Gimignano, aptly nicknamed the “City of Towers.” Walk beneath slim stone giants that once symbolized family wealth and power. Browse local workshops for saffron, Vernaccia wines, and handcrafted pottery. Every corner here feels lifted from a storybook—proof that Tuscany’s history is alive and well on this day trip from Rome to Tuscany.

Chianti Wine Tasting: The Perfect Finale to Your Rome to Tuscany day tour

Late afternoon brings you into the heart of Chianti country, where gently rolling vineyards spread beneath a glowing sky. Gather at an intimate winery for a tutored tasting of Chianti Classico, paired with bruschetta topped with tangy pecorino and artisanal salumi. Between sips, learn about the Sangiovese grape and family-run wine traditions that have endured for generations—an authentic ending to your day trip from Rome to Tuscany.

Tips for Your Day Trip from Rome to Tuscany

• Departure: Rome Termini, early morning high-speed service

• What to Pack: Comfortable walking shoes, sun protection, a light jacket

• Inclusions: Round-trip train tickets, expert English-speaking guides, wine tasting fees

• Group Size: Small groups for a personalized experience

Reserve your spot on this ultimate day trip from Rome to Tuscany and discover why Tuscany’s medieval towns and Chianti wines are celebrated around the world.

Looking for More Tuscan Adventures?

If you’re craving even more of Tuscany’s treasures, check out our Florence and Pisa day trip from Rome, which includes a visit to the Leaning Tower of Pisa. You’ll explore Florence’s Duomo, Ponte Vecchio, and Renaissance highlights with an expert guide, then continue on to Pisa to marvel at its famous Leaning Tower, baptistery, and cathedral. Return to Rome by evening with memories of both medieval villages and Renaissance masterpieces—all in one spectacular getaway.

Reserve both experiences today and craft the ultimate Tuscan journey from the heart of the Eternal City.