Florence to Chianti & Siena Day Trip with Wine Tasting

Summary

Medieval Siena, Chianti wines & San Gimignano in a day from Florence

You’ll wind through Tuscany from Florence to Siena’s winding alleys and grand piazza, taste Chianti wines at a local estate with lunch included, then stroll among San Gimignano’s towers as afternoon light fades. Expect laughter with your guide, real stories from locals, and small sensory moments that linger long after you return.

What’s the experience like?

We rolled out of Florence just after sunrise, the city still rubbing its eyes. Our driver, Marco, pointed out the window as we curved up into the hills—there’s that classic view of Florence everyone wants, but honestly, it’s even better when you’re not expecting it. The air smelled like wet stone and coffee from someone’s thermos. I kept thinking I’d nap on the drive but ended up wide awake, watching olive groves flicker past.

Siena came up around a bend—those brick towers look like they’re leaning in for a secret. Our guide Francesca led us through alleys where laundry hung above our heads and old men argued softly outside tiny bars (she called them “bar sport”). She told us about the Palio horse race right in Piazza del Campo; I tried to imagine horses thundering over those ancient stones. We paused by the Siena Cathedral—didn’t go inside, but even standing outside you get this feeling of something grand and strange. The marble stripes almost look unreal up close.

By midday my stomach was making itself known (loudly). The drive into Chianti was all green waves and cypress shadows. We landed at this family-run winery—can’t remember their last name now, but their dog greeted us before anyone else did. They showed us barrels stacked in cool cellars and poured glasses that tasted like summer heat and earth. Lunch was simple: bread with olive oil so peppery it made me cough, pasta with wild boar ragù, tomatoes that actually tasted like tomatoes. I probably ate too much but nobody cared.

San Gimignano was our last stop—those medieval towers just pop out of nowhere against the sky. We wandered on our own for a bit; I bought some saffron gelato because why not? It melted faster than I could eat it. There was this one moment where everything went quiet except for church bells somewhere far off—I still think about that sometimes when things get noisy back home.

Step-by-step itinerary

Day 1 — Tuscany day trip: Chianti, Siena, San Gimignano

• Pick up in Florence by driver and guide
• Drive through Tuscan hills, stop for photos
• Explore medieval Siena streets
• Visit exterior of Siena Cathedral
• Pause at Piazza del Campo square
• Tour Chianti vineyard and winery
• Enjoy all-inclusive Tuscan lunch with wine
• Visit San Gimignano, explore town freely
• Return to Florence by private coach

Top questions

How long is the Florence to Chianti & Siena day trip?

The tour lasts a full day, departing from central Florence in the morning and returning in the evening.

Is lunch included on the Chianti wine tasting tour?

Yes, a gourmet lunch featuring local Tuscan specialties is included at a family-run estate in Chianti.

Are entry tickets to Siena Cathedral included?

No, entry tickets are not included but your guide can assist if you wish to visit; note it may be closed on Sundays or holy days.

Is pickup included for this day trip from Florence?

The tour includes pickup from a central Florence meeting point via air-conditioned transport.

Can dietary restrictions be accommodated during lunch?

Diets can be accommodated if notified after booking; however, vegan or celiac diets cannot be provided for on this tour.

How much walking is involved in Siena and San Gimignano?

This is a walking tour at a moderate pace; guests should be able to walk without difficulty.

Will there be free time in San Gimignano?

Yes, especially on private tours where guests have extended free time to explore San Gimignano independently.

What’s included

Your day includes pickup by air-conditioned minivan from central Florence with an expert English-speaking guide and professional driver leading the way. You’ll enjoy guided walks through Siena (and San Gimignano for group tours), an all-inclusive Tuscan lunch with wine tasting at a family-run Chianti estate, plus plenty of time to wander medieval streets before heading back to Florence in comfort.