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

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1/16

Duration11h

GroupUp to 60

LanguagesEN

Mobile ticketAccepted

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.

11h

Step-by-step itinerary

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.

Good to know

Moderate physical levelStroller 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.