Siena & San Gimignano Day Trip with Tuscan Lunch & Wine

Summary

Walk Siena’s medieval lanes then sip wine in sunlit vineyards

You’ll stroll Siena’s legendary piazza with a local guide, taste home-cooked Tuscan food paired with estate wines near Monteriggioni, and lose yourself among San Gimignano’s medieval towers (and probably some melting gelato). This small-group day trip from Florence isn’t rushed — there’s space for quiet moments and real conversation along the way.

What’s the experience like?

The day started early in Florence — not too early, thankfully, but enough that the city still felt half-asleep when we climbed into the minivan. Our guide, Giulia, had this way of mixing stories about Siena with little details about her own childhood trips there. I remember her laughing about how locals argue over which contrada has the best Palio horse (she swears it’s Onda, but who knows). The drive out was all rolling hills and those weirdly perfect rows of cypress trees — I kept trying to snap photos but the window glare got me every time.

Walking into Siena’s Piazza del Campo was a bit surreal. It’s bigger than I’d pictured, almost sloping like a shallow bowl, and there were already a few groups clustered around guides waving little flags. Ours just pointed up at the Palazzo Pubblico and said quietly, “This is where centuries of drama happened.” The cathedral — Duomo di Siena — was even more intricate up close; stripes of marble everywhere and this faint incense smell inside that made me pause for a second. We had some free time to wander after that. I grabbed a coffee at a tiny bar where an old man nodded at me like we were both in on some secret.

Lunch was at a winery near Monteriggioni. I didn’t expect much (sometimes “winery lunch” means dry bread and cheese), but they brought out these plates of pappa al pomodoro and wild boar ragu that honestly tasted like someone’s grandmother had cooked them. The wine was bold — Chianti, obviously — and our host explained how each bottle came from vines we could see out the window. There was this moment where everyone just went quiet for a second, looking at the hills through dusty glass. Sunlight on olive leaves is its own kind of magic.

San Gimignano was our last stop. The towers really do look like something out of an old storybook, but what stuck with me more was wandering down Via San Giovanni with gelato dripping onto my hand (hazelnut and saffron — weird combo but good). People were chatting in doorways or just sitting on steps watching tourists go by. I found myself slowing down without meaning to; maybe it was the wine or just that late afternoon Tuscan light making everything feel softer. Anyway, if you go: don’t skip the gelato place with all the certificates in the window — Li laughed when I tried to say “grazie mille” with my mouth full.

Step-by-step itinerary

Day 1 — Tour Siena, lunch, and San Gimignano

• Depart from Florence
• Visit Piazza del Campo in Siena
• See Siena Cathedral
• Pass by Monteriggioni
• Enjoy light lunch with Tuscan wines
• Explore San Gimignano independently

Top questions

How long does the Siena & San Gimignano day trip take?

The tour departs from Florence in the morning and returns around 6:00pm.

Is lunch included on this small group tour?

Yes, lunch is included at a Tuscan winery along with wine tasting.

Do you get free time in San Gimignano?

Yes, there is free time to explore San Gimignano on your own during the tour.

Are entrance fees for Siena Cathedral included?

No, entrance fees for Siena Cathedral are optional and can be paid directly to your guide (€15 per person).

Is transportation provided from Florence?

Yes, roundtrip transportation by air-conditioned minibus or minivan is included.

Can dietary needs be accommodated for lunch?

Vegetarian and gluten-free options are available if requested when booking.

How big is the group on this tour?

This is a small-group tour for more personalized attention.

Is pickup from my hotel in Florence included?

The tour includes pickup from a central meeting point in Florence; hotel pickup is not specified.

What’s included

Your day includes roundtrip transportation from Florence by comfortable minivan or minibus (with Wi-Fi), guided walks through Siena’s highlights plus free time to explore both Siena and San Gimignano at your own pace. Lunch comes at a Tuscan winery near Monteriggioni — expect seasonal dishes paired with their own red wines before heading back in the evening.