Siena & San Gimignano: Chianti Wine Tasting & Tuscan Lunch

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Free cancellationExcellent quality

1/19

Duration9h

GroupUp to 8

LanguagesEN

Mobile ticketAccepted

Four Medieval Towns & a Winery in One Day From Florence

You travel by minivan through four medieval towns — Monteriggioni, Siena, San Gimignano — with a guided walk in Siena and free time to explore each village. Lunch and wine tasting happen at a working Chianti winery, where you taste seven wines, oils, and vinegars alongside a traditional Tuscan meal. Hotel pickup is not included, but you meet at Porta Romana in Florence at 8:45am and return by 6pm the same day.

Step-by-step itinerary

Tuscany tour: villages, wine, and sights

Meet guide near Porta Romana
Travel to Monteriggioni village
Explore Monteriggioni fortress city
Visit Siena and orientation walk
Free time in Siena city
Visit Chianti winery and taste wines
Travel to San Gimignano
Explore San Gimignano freely
Return to Porta Romana

The Experience

There's something about standing in Piazza del Campo in Siena knowing you've got the whole afternoon to wander it — no rushing, no schedule pulling you away. That's the feeling this day trip builds in. You start at 8:45am near Porta Romana in Florence, climb into an 8-seat minivan with maybe seven other people (never a full bus), and your guide starts talking about Tuscany the moment you leave the city. The drive itself is part of it: rolling hills, cypress trees, the light changing as you head south toward wine country.

Monteriggioni comes first — a fortress village so perfectly preserved it's been used for filming Gladiator and Assassin's Creed, and you'll see why the moment you walk through the gate. It's small enough that twenty minutes gets you the whole thing, but long enough that you're not just passing through. Then Siena, where your guide walks you through the artisan quarter and points out the Cathedral before letting you loose for a couple of hours. Most people sit in a café somewhere near Piazza del Campo, the famous Palio race venue, and just sit. You don't have to do anything.

The Chianti region comes next, and this is where the day shifts. You pull up to a local winery — not a tourist trap, a working place — and taste seven different wines alongside extra virgin olive oil and balsamic vinegar. Then lunch: antipasti with Tuscan cured meat and pecorino, lasagna with truffle oil, ribollita soup, cantuccini for dessert. It's not fancy plating; it's the food people actually eat here, and you eat it in the winery with a glass in your other hand. Vegetarian, vegan, and gluten-free versions are available if you need them.

San Gimignano, the last stop, sits on a hilltop with fourteen medieval towers still standing — they call it the Manhattan of Tuscany, and once you're in the cobblestone streets you understand the nickname. You get an hour to walk around, take photos, duck into a shop, sit on a step somewhere. The drive back to Florence takes about an hour, and you're back at Porta Romana by 6pm. The whole day is structured so tightly that you never feel rushed, but you also never feel like you're wasting time waiting for the group.

What’s included

Transport in an 8-seat minivan, scenic drive through the Chianti region, a short visit to Monteriggioni, an orientation walk of Siena with your guide followed by free time to explore, one hour in San Gimignano to wander at your own pace, wine and olive oil tasting at a local winery with seven wines, and a traditional Tuscan meal including antipasti, lasagna with truffle oil, ribollita soup, and cantuccini. Vegetarian, vegan, and gluten-free options are available on request.

Good to know

Easy physical levelPublic transport nearby

Operated by Italy on a Budget tours

Is this one for you?Book this if you want to see the best of Tuscany in a single day without arranging transport, tickets, or timing yourself — the small-group format and fixed schedule mean you move through four towns and a winery without the chaos of a large tour bus.