Siena & San Gimignano: Chianti Wine Tasting & Tuscan Lunch

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.

Options for this experience

2 options

Classic tour from FlorenceGuide in English · 09:00Minivan: an intimate small-group experience, with no more than 8 guests at any time

Private tour from FlorenceGuide in English · 09:00Private 8-seat minivan: a comfortable round-trip journey in an air-conditioned vehicle

You'll see the exact price of each option when you check availability.See dates and prices

Before you book

Days and timesMonday to SaturdayDeparts at 09:00

Book up to4h before

AgesAdult (15 to 79 years) · Under 15: can't be booked

GroupUp to 8

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated today

Good to know

Low physical effortPublic 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.

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Top questions

Do I need to book hotel pickup separately?

No. You meet the group at Porta Romana in Florence at 8:45am. Public transportation to that point is available nearby.

What if I'm vegetarian or have dietary restrictions?

Vegetarian, vegan, and gluten-free versions of the Tuscan meal are available on request when you book.

How many people are usually on the tour?

The minivan holds 8 seats. Groups are kept small: no large buses, and the tour requires a minimum of 4 participants to run.

Is there time to visit the Cathedral in Siena?

Yes. Your guide points it out during the orientation walk, and you have a couple of hours of free time in Siena to visit it if you choose.

What's included in the wine tasting?

Seven different wines, extra virgin olive oil, and balsamic vinegar tasting at a local Chianti winery, plus the traditional Tuscan lunch.

How long is the drive back to Florence?

About one hour. You return to Porta Romana by 6pm.

Is this tour suitable if I have mobility issues?

The tour involves walking through medieval villages on cobblestone streets and is not recommended for travelers with walking disabilities.