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

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Free cancellationTravelers' pick

1/22

Duration11h 30m

GroupUp to 60

LanguagesEN · DE +4

Mobile ticketAccepted

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.

11h 30m

Step-by-step itinerary

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.

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.