San Gimignano: Horseback Ride, Chianti Lunch & Wine Tasting

4.89

(454 reviews)

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?