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Tuscany Day Trip: Siena, San Gimignano, Pisa & Winery Lunch

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Duration12h

GroupUp to 40

LanguagesEN

Mobile ticketAccepted

Medieval towns wine lunch rolling hills and the lean of pisa

You’ll wander Siena’s medieval alleys with a local guide, share laughter over farmhouse lunch and wine overlooking Tuscan hills, explore San Gimignano’s towers (and maybe get lost), then end your day marveling at Pisa’s Leaning Tower as evening falls. It’s not just sights—it’s stories, flavors, small surprises along winding roads.

12h

Step-by-step itinerary

Meet at Santa Maria Novella station
Drive to Siena (1h 15m)
Guided walking tour of Siena (1h)
See Monte dei Paschi bank
Explore Siena's contrade districts
Visit Piazza del Campo
Tour Siena Cathedral interior
Free time in Siena city center
Drive to winery (45m)
Wine tasting and Tuscan lunch
Drive to San Gimignano (15m)
Explore San Gimignano independently
Visit Piazza della Cisterna and gelato
Visit Piazza del Duomo and cathedral
View from La Rocca garden
Drive to Pisa (1h 30m)
Visit Square of Miracles in Pisa
Optional climb of Leaning Tower
Drive back to Florence (1h)

The Experience

I almost missed the group at Santa Maria Novella because I got distracted by a guy arguing with his coffee—Florence mornings, you know? Our guide Elena waved me over with a grin, no judgment. The coach ride out of Florence was quiet at first, everyone still waking up. I remember the sound of rain tapping the windows as we crossed into the hills toward Siena. Elena started telling us about old banking families and how Siena’s wealth was built on pilgrims passing through. I didn’t expect to care about medieval banks before 9am but her stories made it feel alive—plus she slipped in some local gossip about the Palio horse race that had everyone laughing.

Siena’s streets felt like walking through a painting—slick stone underfoot, laundry flapping above us between ochre walls. Our city guide Paolo showed us the Duomo and pointed out details in the marble floor I’d have missed alone (there’s a wolf carved near the altar—he said it’s lucky). He explained how each contrada has its own animal mascot and rivalries get wild during Palio season. Afterward, I sat in Piazza del Campo with an espresso watching two old men argue over soccer scores. There was this smell of rain on warm stone and pastry drifting from somewhere nearby—I wish I’d found that bakery.

The drive to the winery was short but somehow my stomach was already ready for lunch. Fattoria Poggio Alloro sits on a hill with views that don’t even look real—vineyards stretching forever, San Gimignano’s towers poking up in the haze. Lunch was loud and messy in the best way: homemade pasta (the sauce tasted like someone’s grandma made it), salty prosciutto, sharp cheese, and wine that kept appearing before my glass was empty. We tried four wines; I liked the white best but couldn’t pronounce its name (Elena tried to teach me but gave up). Met a couple from Melbourne who swapped travel mishaps with me while we watched clouds chase shadows across the fields.

San Gimignano was smaller than I expected—almost toy-like with its towers and narrow lanes. Elena handed out maps but mostly let us wander on our own. I got lost trying to find “the best gelato in the world” (her words) and ended up sharing a bench with an old woman who asked if I’d come for “the towers or the sweets.” Both, honestly. The gelato did live up to its reputation—creamy saffron flavor that still pops into my head sometimes when I’m daydreaming at work.

Pisa came last, just as golden light started hitting those famous white stones in Piazza dei Miracoli. The Leaning Tower really does look stranger in person—like it’s daring you not to laugh at it. Some people climbed it (I chickened out after seeing those dizzy stairs). Instead I sat on the grass listening to kids run around while our group traded photos and stories from earlier stops. By then my feet were tired but my head felt full—in a good way.

What’s included

Your day includes meeting your guide outside Santa Maria Novella station in Florence before traveling by air-conditioned coach to Siena for a guided walk with cathedral entry.
plenty of free time in both Siena and San Gimignano.
hearty farmhouse lunch with four local wines at an organic estate.
all transport between towns.
plus time to explore Pisa's monuments before returning to Florence in the evening.

Good to know

Moderate physical levelStroller friendlyPublic transport nearbyInfants must sit on laps

Operated by Walkabout Florence Tours