Tuscany Day Trip: Wine Tasting, 2 Wineries & San Gimignano

Summary

Chianti wines, olive groves and medieval towers in one day

You’ll ride out from Florence into classic Tuscan countryside, taste eight different wines at two family-run estates near San Gimignano, sample fresh olive oil and snacks, and have free time to wander medieval streets. Expect laughter over glasses of Chianti—and maybe a new favorite view you can’t quite capture on camera.

What’s the experience like?

I still remember how the air changed as we left Florence. City sounds faded and there was this soft, earthy smell through the van window—kind of grassy but also like old stone. Our guide, Paolo (purple shirt, big smile), started telling us stories about Tuscan families and vineyards before we’d even left the city limits. I wasn’t expecting to feel so awake that early; maybe it was the light or just knowing there’d be wine soon.

The first winery was tucked into a hill near San Gimignano—honestly, I almost missed it because I was staring at the cypress trees lining the road. The owner’s daughter poured our first glass of Vernaccia and handed around bruschetta with tomatoes that tasted like actual sunshine. She laughed when I tried to say “grazie mille” with my mouth full (not my best Italian moment). We tasted eight wines total between both stops—Chianti, Super Tuscans, even a rosé that surprised me. Olive oil and balsamic on bread felt like an extra course every time.

San Gimignano itself is wild—like someone dropped a medieval movie set in the middle of vineyards. The towers really do look like something out of a storybook. We wandered cobblestone streets for an hour or so; I ended up buying saffron from a tiny shop where the owner told me her grandmother still picks crocus flowers by hand. It’s funny what sticks with you from these trips—the taste of cold white wine outside under fig trees, or just watching Paolo chat with local winemakers in rapid-fire Italian while we tried to keep up.

Step-by-step itinerary

Day 1 — Tuscany wineries and San Gimignano visit

• Meet at Piazza della Calza at 9:45am
• Drive to first winery in Ulignano
• Taste wines and local delicacies at first winery
• Visit second winery near San Gimignano
• Taste wines including Vernaccia and rosé
• Explore San Gimignano medieval town
• Return to Florence by 5:00pm

Top questions

How long is the Tuscany wine tour from Florence?

The tour starts at 10:00am and returns around 5:00pm, so it lasts about 7 hours.

Are lunch or snacks included during the Tuscany wine tasting day trip?

You’ll get Tuscan snacks like bruschetta with tomatoes plus tastings of olive oil and balsamic vinegar at the wineries.

Is hotel pickup included for this Tuscany day trip?

No hotel pickup; you meet at Piazza della Calza by Porta Romana for departure.

How many wineries do you visit on this tour?

You visit two different wineries in the Chianti region near San Gimignano.

What types of wine are tasted during the Tuscany wine tour?

You’ll try eight wines including Chianti, Super Tuscans, Vernaccia di San Gimignano, and a rosé.

Is there free time in San Gimignano on this day trip?

Yes, you have time to explore San Gimignano’s medieval streets and shops on your own.

Is this Tuscany wine tour suitable for solo travelers?

Yes—it’s small-group style and a good way to meet other travelers along the way.

Are children allowed on this Tuscany wine tasting tour?

No—the minimum age is 18 years old; no kids allowed.

What’s included

Your day includes transport from Florence by air-conditioned minivan or coach, guided tastings at two different wineries (with eight wines plus local olive oils and balsamic), Tuscan snacks like bruschetta with tomatoes, plenty of time in San Gimignano’s medieval center—and an expert local guide who knows all the best stories behind every glass poured.