Pisa, San Gimignano & Siena: Chianti Wine Tasting Day Trip

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6 options

Guide in English, Spanish or Italian07:30

Guide in 4 languages07:30

Guide in 4 languages07:30

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Guide in FrenchFrom 30 Oct · 07:30

Guide in 6 languages07:30

Guide in FrenchFrom 30 Oct · 07:30

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

Three Tuscan Towns & a Chianti Lunch in One Morning-to-Evening Loop

You leave Florence at dawn, spend the morning exploring Pisa's cathedral complex and Leaning Tower, then drive through Chianti vineyards to a working winery for lunch and wine tasting. Afternoon takes you through the medieval streets of San Gimignano, followed by a guided walk through Siena's most important squares and the Cathedral. You return to Florence in the evening with a professional guide, air-conditioned bus, and all transport included.

Step-by-step itinerary

Stops and time at each

1. Leaning Tower of Pisa40m
2. Pisa Cathedralpass by
3. Monumental Cemetery of Pisapass by
4. Piazza dei Miracolipass by
5. Pisa Baptisterypass by
6. Pubblico Palacepass by
7. Siena Cathedralpass by

Visit Pisa, San Gimignano, and Siena

• Depart from Florence city centre
• Tour Pisa cathedral and baptistery
• Visit Monumental Cemetery of Pisa
• Admire Piazza dei Miracoli
• Optional climb Leaning Tower of Pisa
• Drive through Chianti countryside
• Wine tasting and light lunch at Chianti winery
• Explore San Gimignano cobbled streets and shops
• View Piazza del Duomo and Piazza della Cisterna
• Panoramic Chianti countryside view
• Guided tour of Siena squares and Contrade
• Free time for coffee, Pan Forte, and shopping
• Return to Florence city centre

The Experience

You're driving out of Florence before eight, heading northwest toward Pisa with the Chianti hills rising ahead. The bus moves through the countryside for about an hour, and then the Piazza dei Miracoli appears: the cathedral, baptistry, and that tilted tower all standing in one pale-stone plaza. You get time to walk around, climb the Leaning Tower if you've added that ticket, or just stand in the grass and look at how the whole thing leans without falling. The Monumental Cemetery is there too, a quieter corner where the legend says bodies used to decompose in a single day because of the soil.

After Pisa, the drive swings south into the Chianti region, and the landscape changes: rolling vineyards, cypress trees, stone farmhouses on hillsides. You pull into a rustic winery on the slopes near San Gimignano, where lunch happens: local cheeses, cold cuts, bruschetta, and three wines you taste through. It's not rushed. Then you're loose in San Gimignano itself, the medieval town with its famous towers and narrow cobbled streets. Piazza della Cisterna and Piazza del Duomo are the two main squares, both lined with craft shops and small cafés. You can wander as long as you want before heading to the final stop.

Siena comes last, in the late afternoon. The professional guide (if you've booked the guided option) walks you through Piazza del Campo (that shell-shaped square that hosts the Palio horse race twice a year), and past the Cathedral, pointing out the Contrade, the neighborhood districts that define the city's identity. After the tour, you have free time for coffee, a slice of Pan Forte if you want it, or more shopping. The bus collects everyone from the city center and heads back to Florence, arriving in the evening. The whole day runs from early morning to dusk, and you see four major Tuscan destinations without arranging transport, tickets, or timing yourself.

What’s included

Your day includes hotel pickup (if booked separately), air-conditioned bus transport with Wi-Fi, entry to Pisa's cathedral complex and Monumental Cemetery, lunch at a Chianti winery with three wines and local specialties, free time in San Gimignano's medieval squares, a professional multilingual guide in Siena (if selected), and return to Florence city center in the evening. Leaning Tower tickets and the Siena guided tour are optional add-ons.

Days and timesDaily · 07:30

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

Meeting point and pickupNo pickup · ends where it startsMeeting point, per the operator: “Meeting point: 20 minutes before the start of the tour at our Sightseeing Experience Visitor Center located inside the Santa Maria Novella train station in the …”

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

Prices and times updated today

Good to know

Easy physical levelStroller friendlyPublic transport nearbyInfants must sit on laps

Operated by Sightseeing Experience

Is this one for you?This works well if you want to see four major Tuscan destinations in a single day without renting a car or coordinating your own schedule: the fixed itinerary and included transport are what make it possible to move between Pisa, the Chianti hills, San Gimignano, and Siena all in one morning-to-evening loop.

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Top questions

What languages is the guide in?

Live guide in English, Spanish, French, German, Italian and Portuguese.

Can children come?

4 to 12 years; under 4, free.

What time does the tour leave Florence?

Early morning departure from Sightseeing Experience Visitor Center at Florence's Santa Maria Novella train station. The bus returns to the same point in the evening.

Is the Leaning Tower climb included?

No. Leaning Tower entry is an optional add-on you can select when booking. Children under 8 cannot enter the tower.

What's included in the winery lunch?

Light lunch with local specialties (bruschetta, pecorino cheese, cold cuts) plus a tasting of three Chianti wines.

Do I need to book the Siena guided tour?

The professional guide in Siena is optional. You can choose a version without the guide, though the tour still includes transport and free time in all three towns.

How long do I spend in each town?

Pisa gets the morning, San Gimignano gets mid-afternoon free time after lunch, and Siena gets the late afternoon with either a guided tour or independent exploration.

Are there vegetarian or dietary options?

Yes. Notify the operator by email after booking if you need a vegetarian menu or have food intolerances, and they'll arrange an alternative lunch at the winery.

What if I'm late to the meeting point?

The tour departs on schedule with no waiting time for late arrivals. Maximum punctuality is required at all meeting points during the day.