San Gimignano: Horseback Ride, Chianti Lunch & Wine Tasting

Summary

Horse ride through vineyards medieval streets and Chianti flavors

You’ll ride horses through Tuscan vineyards near San Gimignano, wander medieval streets with a local guide, sample world-class gelato, then share a rustic Chianti lunch and wine tasting at a family-run winery. Expect laughter, new tastes—and maybe a little dust on your shoes by the end.

Step-by-step itinerary

Day 1 — Horseback ride, San Gimignano visit, lunch

• Horseback ride through Tuscan countryside
• Guided visit to San Gimignano village
• Free time for shopping and gelato
• Tuscan lunch with guided wine tasting

Top questions

Is this horseback tour near San Gimignano suitable for beginners?

Yes, no prior riding experience is needed and guides provide orientation before starting.

Does the day trip include transportation from Florence?

Yes, roundtrip transportation by air-conditioned minivan from Florence is included.

Can I join if I don’t want to ride horses?

Yes, you can skip the horseback ride for a discount and enjoy farm walks or other activities instead.

Is lunch included on this private wine tour in Chianti?

Yes, an authentic Tuscan light lunch with wine pairing at a local winery is included.

Are vegetarian or gluten-free meals available?

Yes, vegetarian, vegan and gluten-free options are available upon request.

How long is the horseback ride?

The horseback ride lasts about one hour through olive groves and countryside.

Is San Gimignano accessible for wheelchairs or strollers?

The tour is wheelchair accessible and infants can join in prams or strollers.

What languages does the guide speak?

The guide speaks English, Spanish, and Italian.

What’s included

Your day includes comfortable roundtrip transport from Florence by AC minivan, pre-ride orientation with helmet and insurance for your horseback adventure through Tuscan hills, guided visit to San Gimignano’s medieval streets (with time for gelato), an authentic light lunch paired with Chianti wines at a local winery—including tastings of their own olive oil—and plenty of chances to buy or ship local products before heading back.

What’s the experience like?

By the time we were halfway down that dusty path outside San Gimignano, my horse—Nocciola—had already figured out I was a total beginner. The guide, Marco, just grinned and told me to relax (“She knows the way better than I do,” he said). The air smelled like wild herbs and something sweet from the olive trees. We passed rows of vines so close you could reach out and touch them—somehow it felt quieter out there than anywhere I’d been in Italy. I kept hearing birds I couldn’t name. My legs were a bit wobbly but honestly, I didn’t care; it was kind of freeing not knowing what came next.

After the ride (and a lot of nervous laughter), we wandered into San Gimignano’s stone streets. Our guide pointed out where locals still hang their laundry between windows—like postcards come to life. There was this tiny gelato shop, Dondoli, that Marco insisted we try (“World champion!” he said with a wink). I ordered pistachio and nearly dropped it when someone’s Vespa backfired nearby. The town itself felt ancient but lived-in—kids running around the main square, older men arguing softly about football under the towers’ shadows.

The best part? Lunch at a Chianti winery just outside town. Long wooden tables set with mismatched plates, sun spilling in through open doors. We tasted three wines (I liked the second one best but forgot its name—too busy dipping bread in olive oil they pressed right there). Our host explained each glass without any snobbery; just stories about his grandfather’s harvests and how rain changes everything. By then I’d stopped worrying about how dusty my shoes were or if my Italian sounded ridiculous. Sometimes you just sit back and let Tuscany do its thing, you know?