Tuscany Day Trip: Siena, San Gimignano & Chianti Wine Tasting

Summary

Siena’s Piazza, San Gimignano towers and Chianti vineyards in one day

You’ll wander ancient streets in Monteriggioni, stand in Siena’s famous piazza with your guide sharing stories, taste traditional Tuscan pastries over lunch, then stroll San Gimignano’s towered skyline before ending your day sipping Chianti wines at a rustic estate. It’s not just sightseeing—it actually feels like you’re living inside Tuscany for a day.

What’s the experience like?

The first thing I noticed in Monteriggioni was the sound—my shoes crunching on old stones, and a group of locals laughing near the gate. It felt like we’d slipped into another century. Our guide, Lucia, pointed up at the ring of towers and told us Dante once wrote about this place. I tried to picture soldiers watching from those walls, but mostly I just smelled rosemary on the breeze and watched a cat sunning itself by a doorway. Not how I pictured starting a Tuscany day trip from Florence, but honestly it set the mood.

In Siena, Lucia led us through tangled lanes until suddenly we were standing in Piazza del Campo. The square really does feel like an open-air bowl—sunlight bouncing off pale stone, people sitting right on the bricks eating pastries. She explained how the Palio horse race takes over the whole city twice a year (I can’t imagine that chaos). Inside the cathedral, it was quieter than I expected—just footsteps echoing and that faint waxy smell you get in old churches. We had lunch tucked away in a tiny spot where I tried ricciarelli for dessert. Still thinking about those almond cookies.

San Gimignano came next—those towers really do look like medieval skyscrapers. We wandered at our own pace; I ended up buying gelato from a guy who insisted his pistachio was “the best in Italy.” He might be right. After that it was all rolling hills and olive trees as we drove to a Chianti winery. The tasting wasn’t rushed—just sitting outside with glasses of red and slices of salami while someone’s dog begged at our feet. Lucia told stories about her grandmother making olive oil by hand (she laughed when I tried to say “olio extravergine” properly). We left just before sunset, everyone quiet for once, watching golden light slide over vineyards. That view stuck with me longer than any photo.

Step-by-step itinerary

Day 1 — Explore Medieval Tuscany and Wine Tasting

• Depart from Florence
• Visit Monteriggioni hilltop castle
• Explore Siena's Piazza del Campo
• Visit Siena Cathedral at Piazza del Duomo
• Enjoy light lunch with Tuscan products
• Stroll in San Gimignano medieval town
• Taste ice cream in San Gimignano
• Visit Chianti wine estate
• Taste wines and local products

Top questions

How long is the Tuscany day trip from Florence?

The tour lasts a full day, including stops at Monteriggioni, Siena (with guided tour), San Gimignano, and a Chianti winery before returning to Florence.

Is lunch included during the Siena tour?

Yes, you’ll have a light lunch with traditional Tuscan products and pastries in Siena as part of the tour.

Do you get free time in San Gimignano?

Yes, there is free time to explore San Gimignano at your own pace after arriving with the group.

Are wine tastings included on this Tuscany tour?

The tour includes wine tasting at a Chianti estate along with samples of olive oil and local products.

Is there hotel pickup for this day trip?

No hotel pickup is mentioned; departure is from Florence by GT coach equipped with WiFi.

Are guides multilingual?

Yes, expert multilingual guides lead the tour; language availability varies by season and group size.

What should I wear to visit Siena Cathedral?

A dress code applies: knees and shoulders must be covered for both men and women to enter places of worship like Siena Cathedral.

Is this Tuscany tour suitable for children or infants?

Infants can join if seated on an adult’s lap or in a stroller; specialized infant seats are available upon request.

What’s included

Your day includes travel by comfortable coach from Florence with free WiFi onboard, guided walking tours (with headsets) through Siena’s historic center and cathedral entry (where dress code applies), free time to explore Monteriggioni and San Gimignano on your own terms, a light Tuscan lunch with pastries in Siena, plus wine tasting with olive oil sampling at an authentic Chianti estate before heading back home in the evening.