San Gimignano Siena Chianti Day Trip: Wine Tasting Lunch

Options for this experience

3 options

Guide in English or Spanish08:00

Guide in English or Spanish08:00

Guide in English or Spanish08:00

You pick the guide language when booking. Options with the same name differ in details you'll see when you pick a date.

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

Medieval towers, rolling vineyards, and a winery lunch built into one morning-to-evening route

A full-day tour from Florence visits the UNESCO hilltop town of San Gimignano, the walled village of Monteriggioni (April–October), and Siena, with a guided Chianti winery stop for wine tasting and three-course farm-to-table lunch included. A licensed guide in English or Spanish leads the route. The Cathedral and Piccolomini Library are optional add-ons. From November to March, Monteriggioni is skipped and the day ends about 30 minutes earlier. Comfortable walking shoes and covered shoulders and knees are required for entry to religious sites.

Step-by-step itinerary

Stops and time at each

1. Pubblico Palace15m
2. Siena Cathedral30m · entry included
3. Piccolomini Library15m · entry included

Tuscany day trip from Florence

• Explore San Gimignano town and towers
• Visit Piazza della Cisterna square
• Walk along San Gimignano medieval walls
• Free time in Monteriggioni village (seasonal)
• Wine tasting and three-course lunch in Chianti
• Guided walking tour of Siena city
• Visit Piazza del Campo and Palazzo Pubblico
• See Siena Cathedral interior (if option selected)
• Free time in Siena before return

The Experience

The day starts with roughly two hours in San Gimignano, the medieval "town of towers" perched on a hilltop with panoramic views across the Tuscan countryside. The town's 13th-century walls and narrow lanes lined with artisan shops and award-winning gelato stands are yours to wander at your own pace. Piazza della Cisterna, the heart of the town, sits surrounded by well-preserved towers and medieval stone paving: the kind of square filmmakers and photographers return to. You'll have time to climb a tower, browse boutiques, or simply stand still and look.

From April through October, the route includes Monteriggioni, a perfectly preserved fortress village encircled by intact ramparts where you can stroll the piazza and browse craft shops before heading into the Chianti hills. The winery stop is the anchor of the afternoon: a guided cellar visit followed by a three-course lunch built from farm ingredients, paired with three Chianti wines and finished with cantucci. Vegetarian and gluten-intolerant options are available if you request them at booking. A licensed multilingual guide leads you through the whole day. For groups of eight or fewer, a driver-guide may replace the separate escort, though the itinerary stays the same.

Siena comes in the late afternoon as a guided walking tour through the city's Gothic heart: Piazza del Campo, the Palazzo Pubblico, and the Cathedral if you've chosen that option. Earphones are provided so you can hear the guide over the crowds. The Cathedral entrance and the Piccolomini Library, a Renaissance gem inside the Duomo adorned with frescoes by Pinturicchio, are optional. If you skip them, you'll have free time to sip an espresso, browse the city's boutiques, or continue exploring on your own before the return to Florence. The entire day runs about 11 hours from pickup to drop-off.

What’s included

• The tour includes comfortable air-conditioned coach transport from Florence with a licensed multilingual guide.
• entry and a guided walking tour of Siena with earphones provided.
• the Chianti winery experience with a guided cellar visit, three wines tasted, and a three-course farm-to-table lunch.
• and staff assistance at the meeting point. The Cathedral entrance and Piccolomini Library visit are included only if you select that option at checkout.

Days and timesDaily · 08:00

AgesAges 13+ · 4 to 12 years · Under 4 — Free

Meeting point and pickupNo pickup · ends where it startsMeeting point, per the operator: “Check in time: 07:45am - Montelungo Square, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing…”

Cancellation and refundsFree cancellation up to 24h 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 levelStroller friendlyInfant seats availablePublic transport nearby

Operated by CAF Tour and Travel - Gray Line Florence

Is this one for you?Choose the guided tour with Cathedral if you want the interior of the Duomo and the Piccolomini Library's frescoes included. Pick the semi-independent option if you prefer to explore Siena on your own after the winery lunch. The bilingual Siena visit (November–March) works well if you travel with both English and Spanish speakers. The monolingual option (April–October) keeps the pace steady for single-language groups.

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Top questions

What languages is the guide in?

Live guide in English and Spanish.

Can children come?

4 to 12 years; under 4, free.

What is San Gimignano like when you get there?

San Gimignano is a UNESCO-listed medieval hilltop town famous for its towers and panoramic views across the Tuscan countryside. The town's narrow lanes, well-preserved medieval architecture, and artisan shops line the streets. Piazza della Cisterna at its center is paved with medieval stones and surrounded by historic buildings and towers. You'll have about two hours of free time to explore at your own pace.

Does the tour include the Siena Cathedral?

The Cathedral entrance is optional. You choose it at checkout. If you select it, a guided visit to the Cathedral of Santa Maria Assunta is included, along with entry to the Piccolomini Library inside the Duomo, which houses Renaissance frescoes by Pinturicchio. Without that option, you'll have free time in Siena to explore on your own.

What does the winery experience include?

The winery stop includes a guided cellar visit, a tasting of three Chianti wines, and a three-course farm-to-table lunch with local ingredients, ending with cantucci. Vegetarian and gluten-intolerant options are available. Request them when you book.

Does the tour visit Monteriggioni?

Monteriggioni, a walled fortress village, is included April through October. From November to March, the itinerary skips Monteriggioni and returns to Florence about 30 minutes earlier.

What should I wear?

Comfortable walking shoes are recommended for the day. A dress code is strictly enforced for entry to the Cathedral and other religious sites: knees and shoulders must be covered for both men and women. No shorts or sleeveless tops. Failure to comply will result in refused entry.