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

Summary

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.

What’s the experience like?

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.

Step-by-step itinerary

Day 1 — Tuscany day trip: Siena, winery, San Gimignano, Pisa

• 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)

Top questions

How long is the Tuscany day trip from Florence?

The tour lasts a full day, starting around 8:00am from Florence and returning after visiting Siena, San Gimignano, Pisa, plus lunch at a winery.

Is lunch included on this Tuscany day tour?

Yes, lunch is included at an organic family-run winery near San Gimignano with homemade pasta, cured meats, cheeses, salad and wine tasting.

Can you climb the Leaning Tower of Pisa on this tour?

You can upgrade to include skip-the-line tickets for climbing Pisa's Leaning Tower; otherwise you have free time to explore outside.

Are there vegetarian or gluten-free options for lunch?

Vegetarian options are available for lunch; gluten-free or other special diets cannot be accommodated except vegetarian.

How much free time do you get in each town?

You’ll have guided tours plus some free time in Siena and San Gimignano to explore or shop independently before meeting your group again.

Is pickup included for this Tuscany day trip?

No hotel pickup; you meet your guide outside Santa Maria Novella train station in Florence for departure by coach.

Are children allowed on this tour?

Children can join but must be at least 8 years old to climb Pisa's Leaning Tower; younger kids can join other parts of the tour.

What should I wear or bring for this tour?

Dress comfortably for walking on uneven surfaces; bring layers for changing weather and maybe an umbrella if rain is forecasted.

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.