Tuscany: Siena, San Gimignano & Chianti Private Day Trip

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Free cancellationExcellent quality

1/16

Duration8h

GroupPrivate

LanguagesEN · ES

PickupAt your hotel

Siena’s marble cathedral, San Gimignano’s towers, Chianti’s rolling vineyards

You’ll wander Siena’s medieval streets with time to explore at your own pace before tasting real gelato under San Gimignano’s ancient towers. Enjoy flexible photo stops across Chianti’s vineyards and—if you want—sip local reds at a small winery before heading back to Florence with sunset views lingering behind you.

Step-by-step itinerary

Explore Siena, San Gimignano, and Chianti

Pickup from Florence accommodation
Drive to Siena through rolling hills
Explore Siena independently for two hours
Visit Piazza del Campo and enjoy cappuccino
Tour Siena Cathedral and Piccolomini Library
Drive to San Gimignano and view medieval towers
Explore San Gimignano and Piazza della Cisterna
Drive through Chianti region with photo stops
Optional Chianti wine tasting and vineyard tour
Buy Chianti wine souvenirs
Return to Florence accommodation

The Experience

Hands gripping a warm cappuccino, I watched a group of Sienese teens sprawl across the sloping Piazza del Campo — just chatting and laughing like it was any other Tuesday. Our driver had dropped us right by the Siena Cathedral (I still can’t get over how close you get on a private tour), so we’d wandered through those shadowy stone lanes first. The Duomo’s marble stripes looked almost unreal up close — pinks and greens and blacks all swirled together. Inside, I caught this faint scent of candle wax and old paper in the Piccolomini Library. Didn’t expect that to stick with me.

We had two hours to roam Siena on our own — enough time to get lost in side streets and peek into little shops selling wild boar salami (I chickened out). The local barista grinned when I tried to order in Italian; she corrected my accent but handed over a perfect espresso anyway. After that, we piled back into the Mercedes van — air conditioning humming softly — and headed for San Gimignano. Our driver pointed out those “medieval skyscrapers” as we got closer. It really does look like a tiny Manhattan from a distance, but quieter. I remember leaning against the old city wall, just breathing in olive trees and distant woodsmoke.

San Gimignano felt smaller than I expected, but every alley twisted into another postcard view. We found gelato in Piazza della Cisterna (the pistachio was actually salty — weirdly good), then just sat on the steps people-watching for a while. There was this older couple arguing gently about directions in French; made me smile. One hour there went fast.

The drive through Chianti after that—honestly, it’s hard not to stare out the window the whole way. Vineyards rolling forever, little stone villages popping up between cypress trees. We stopped for photos whenever someone spotted something pretty (which was often). If you add the wine tasting option, they’ll take you right to a family-run estate—our guide chatted with the winemaker about last year’s harvest while we sipped Chianti Classico and nibbled pecorino cheese. The sun started dipping behind the hills as we drove back toward Florence; everyone got quiet for a bit. Sometimes I still think about that light.

What’s included

Your day includes hotel pickup and drop-off from Florence by private Mercedes vehicle with air conditioning and WiFi onboard.
an expert driver who shares stories as you go.
plenty of independent sightseeing time in Siena, San Gimignano and across the Chianti wine region.
flexible photo stops whenever something catches your eye.
plus an optional local wine tasting experience if selected during booking before returning comfortably to your accommodation.

Good to know

Easy physical levelStroller friendlyInfant seats availablePets welcomePublic transport nearbyNot for heart conditionsInfants must sit on laps

Operated by Ciao Florence Tours Srl