Florence: Horseback Ride San Gimignano & Chianti Wine Tasting

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Free cancellationTravelers' pick

1/35

Duration7h

GroupUp to 16

LanguagesEN · IT +1

Mobile ticketAccepted

You've Never Ridden Before—and That's Exactly Who This Day Is Built For

You ride through vineyards and hills for just over an hour with no experience required, visit the medieval town of San Gimignano with free time to explore, and finish with an authentic Tuscan lunch and guided wine tasting at a local winery. Pickup and drop-off in Florence are included, along with your helmet, insurance, and a multilingual guide who handles all the logistics so you just show up.

Step-by-step itinerary

Horseback ride, San Gimignano visit, lunch

Meet at 9 am in Florence
Horseback ride through vineyards and hills
Enjoy coffee, drinks, and honey tasting
Guided visit to medieval San Gimignano
Free time for shopping and gelato
Authentic Tuscan lunch with wine tasting
Taste olive oil and balsamic vinegar

The Experience

The moment you realize you're about to sit on a horse for the first time, something shifts. You're standing at the farm outside Florence at 9 am, helmet in hand, and your guide is already laughing at the question you haven't even asked yet. But here's the thing: this horseback ride through the Tuscan countryside requires absolutely no prior experience. You get a pre-ride orientation, the horse knows what it's doing far better than you do, and within twenty minutes of leaving the farm you're riding through vineyards and olive groves like you've been doing this for years. The first hour takes you across rolling hills and native woods, past the kind of views that make you understand why people move to Tuscany and never leave. There's honey tasting back at the farm too—locally produced, the real thing—and coffee before you head out.

Then comes San Gimignano, the medieval town that looks like it was built yesterday by someone who'd only read about the Middle Ages in a storybook. Narrow streets, towers everywhere, and the main squares are genuinely stunning. Your guide walks you through the highlights, but you get free time to wander, find the gelato place that's won world championships (yes, really), and just sit on a stone wall if you want to. The town fills up with tourists by midday, but you're there early enough that it still feels like a place where people actually live.

Lunch happens at a Chianti winery, and it's not a rushed thing. You get an authentic Tuscan meal—vegetarian, vegan, and gluten-free options are available if you need them—paired with a guided wine tasting. The winery walks you through their selection, shows you the olive oil and balsamic vinegar they make, and you understand why this region tastes the way it does. The whole experience is about eight hours from pickup to drop-off, and you're back in Florence by late afternoon.

If someone in your group doesn't want to ride, they still come along. They get a €20 discount, skip the horse part, and instead walk around the farm, learn about beekeeping and honey production, watch how saffron is harvested, see the olive oil process in action, and have drinks while everyone else is in the saddle. So nobody gets left behind, and nobody feels like they're missing out.

What’s included

Roundtrip transportation by air-conditioned minivan from Florence, pre-ride orientation with helmet and insurance, just over one hour of horseback riding through vineyards and countryside, guided visit to San Gimignano with free time to explore, authentic Tuscan lunch with wine pairing at a Chianti winery, guided tasting of wines and extra virgin olive oil produced by the winery, honey tasting at the farm, and the option to purchase and ship local products. If you skip the horse ride, you get farm activities including beekeeping, saffron cultivation, and olive oil production instead.

Good to know

Easy physical levelWheelchair accessibleAccessible transportStroller friendlyInfant seats availablePublic transport nearbyNot for pregnant travelers

Operated by Chianti Wine Tour

Is this one for you?Book this if you want to ride through the Tuscan countryside without worrying about experience, logistics, or arranging your own transport to San Gimignano and a winery—the fixed itinerary and included lunch mean you show up at 9 am and everything else is handled.