Siena & San Gimignano: Medieval Towns, Chianti Wine & Lunch

Four Medieval Towns & a Winery in One Day From Florence

You visit four medieval towns (San Gimignano, Monteriggioni, Siena), and a Chianti winery, all in one day with transport, a three-course lunch, wine tasting, and an English-speaking guide included. The pace is set. You just show up at the Florence meeting point and let the coach and the escort handle the logistics.

Step-by-step itinerary

Stops and time spent at each3 stops

1. Basilica of Santa Maria Assunta2h
2. Siena Cathedral15m
3. Pubblico Palace30m

Tuscany tour: San Gimignano to Siena

• Explore San Gimignano historic center
• Visit Monteriggioni fortress village
• Drive scenic Chiantigiana road
• Wine tasting and lunch at winery
• Free time to explore Siena city
• See Siena Cathedral exterior and interior
• Visit Piazza del Campo and relax

The experience

The coach pulls away from Florence before dawn, and by the time you reach San Gimignano, the towers are catching first light: fourteen of them, medieval and narrow, rising above the Val d'Elsa like a skyline that stopped changing five hundred years ago. You have time to wander the UNESCO-listed center on your own, past the Basilica di Santa Maria Assunta and down lanes so quiet you hear your footsteps. Artisan shops line the streets, and there's always a gelateria if you need one. The town doesn't feel like a museum. It feels like you've stepped into something that's still lived in, just slowly.

Then Monteriggioni appears: a perfect circle of 13th-century walls wrapped around a tiny piazza, so intact it looks like someone built it last year and then forgot to add anything else. You walk the ramparts, take photos from the gates, and leave. It's quick, but it stays with you. After that, the coach follows the Chiantigiana road, the scenic route through Chianti, past vineyards and olive groves and stone farmhouses that seem to have grown out of the hillside. At a cozy winery, a guide walks you through three Chianti tastings. The wines change depending on the vintage, but they're always paired with a three-course lunch made from zero-mile ingredients: pasta, local cheese, vegetables from the property. It ends with cantucci and vin santo, the almond biscuits softened in sweet wine, the way it's done here.

Siena gets the afternoon. You have free time to find your own rhythm: narrow Gothic lanes, noble palaces, enotecas where locals sit over wine and conversation. The Duomo is striped marble and ornate, worth a quick look inside. Piazza del Campo, the shell-shaped square where the Palio horse race happens every summer, is where you'll end up eventually, sitting at a café, watching the light change on the terracotta buildings. The tour escort is with you the whole day, but the stops in Siena are yours to shape.

The 11-hour day includes round-trip transport from Florence in an air-conditioned coach, the winery visit with three wines and lunch, and an English-speaking guide or driver-guide depending on group size. Vegetarian and gluten-free options are available at the winery. You need to bring your original ID, arrive on time at the Florence meeting point, and wear comfortable walking shoes. The medieval streets are stone, and you'll be on your feet more than you expect. From November through March, Monteriggioni is skipped and you return to Florence about thirty minutes earlier.

What’s included

Your day includes hotel or meeting-point pickup in Florence, round-trip transport by air-conditioned coach, an English-speaking tour escort or driver-guide, entry to San Gimignano and Monteriggioni, a guided winery visit with cellars and vineyards, a three-course traditional Tuscan lunch with local ingredients, tastings of three Chianti wines plus extra virgin olive oil, balsamic vinegar, and vin santo, and free time to explore Siena independently. Vegetarian and gluten-free options are available at the winery upon request.

Before you book

Lasts 11h, runs every day at 08:00, from € 79 per person, with a live guide in English and with free cancellation up to 24 h before.

Days and timesEvery dayDeparts at 08:00

Book up toStart time

AgesAdult (13 and older) · Child (4 to 12 years) · Infant (under 4): free

GroupUp to 60 · max 8 per booking

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.It may be canceled if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated today

Good to know

Moderate physical effortStroller-friendlyInfant seats availablePublic transport nearby

Operated by CAF Tour and Travel - Gray Line Florence

Is this one for you?Choose this tour if you want the main Chianti and medieval Siena highlights in a single day without arranging transport, winery bookings, or timing yourself: the fixed schedule and English-speaking guide mean you arrive at Florence, get on the coach, and everything else is handled.

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Top questions

Can children come?

Yes. Ticket types: Child (4 to 12 years); Infant (under 4): free.

How long is the tour?

11 hours total, departing from Florence in the morning and returning in the evening.

What's included in the winery lunch?

A guided tasting of three Chianti wines, a three-course traditional Tuscan lunch made from local ingredients, and vin santo with cantucci at the end.

Is Monteriggioni always on the itinerary?

No. From November to March, the stop at Monteriggioni is removed, and the return to Florence is about 30 minutes earlier.

Do I need to book the stops in Siena in advance?

No. Your free time in Siena is unscheduled. You explore at your own pace and rejoin the group at a set time for the return to Florence.

Are vegetarian or gluten-free meals available?

Yes, both are available at the winery, though cross-contamination cannot be fully excluded.

What should I bring?

Your original ID is mandatory. Comfortable walking shoes are strongly recommended, as the medieval towns have stone streets and uneven terrain.

What if I'm late to the meeting point?

You won't be able to join the tour or receive a refund or reschedule. Arriving on time at the check-in is mandatory.

Is the tour guide the same person all day?

Yes. An English-speaking tour escort accompanies the group throughout. For small groups of up to 8 people, this may be a driver-guide instead, but the itinerary remains the same.