Tuscany Day Trip: Siena, Pisa & San Gimignano Private Tour

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Free cancellationExcellent quality

1/16

Duration10h

GroupPrivate

LanguagesEN · ES

PickupAt your hotel

Medieval towers, winding streets and Tuscan hills in one day

You’ll cross Tuscany in comfort with your own driver, wandering Siena’s medieval lanes and marveling at its cathedral mosaics before tasting gelato in San Gimignano’s quiet squares. End your day beneath Pisa’s famous tower as sunset colors sweep across ancient stone — it’s less about checking boxes than soaking up moments you’ll replay long after you’re home.

10h

Step-by-step itinerary

Private tour of Siena, San Gimignano, Pisa

Pickup from Florence hotel
Drive to Siena through Tuscan countryside
Explore Siena near Cathedral
Visit Piazza del Campo and cafes
See Torre del Mangia (optional climb)
Tour Siena Cathedral interior
Drive to San Gimignano with photo stops
Explore San Gimignano town and viewpoint
Visit Piazza della Cisterna and Duomo
Enter San Gimignano Cathedral
Drive to Pisa
Visit Leaning Tower of Pisa (optional climb)
Tour Pisa Cathedral
Shop for souvenirs in Pisa
Return drive to Florence hotel

The Experience

I didn’t expect to start my morning in Florence watching the city fade behind tinted windows, but there we were — me, my partner, and our driver Marco (who had a playlist of old Italian songs that made the drive feel like a movie). The air outside was already warming up but inside the Mercedes it was cool, with bottled water and that faint new-car smell. I caught glimpses of vineyards rolling by, olive trees twisting in the sun. Marco pointed out a hilltop village — “That’s where my grandmother makes olive oil,” he said. It made me wish I could stay longer in every place.

Siena came at us suddenly: narrow lanes opening into Piazza del Campo, locals chatting over tiny coffees. I tried to order a cappuccino and managed to make the barista laugh — apparently you don’t order those after breakfast here. The marble stripes of Siena Cathedral looked almost unreal up close; inside it was hushed except for footsteps echoing on the mosaic floor. Our guide told us about Michelangelo working here when he was young — I touched one of the cold stone columns just because he might have too. We wandered past shops selling panforte (I bought some and immediately regretted not buying more).

The drive to San Gimignano felt like slipping back in time. Those towers really do look like something out of a storybook — or maybe a medieval Manhattan if you squint. We had an hour to roam; I got lost twice but found myself in front of a gelateria both times (not complaining). There’s this spot overlooking the countryside where everything goes quiet except for church bells and distant voices. That view sticks with me more than any photo.

Pisa was last — late afternoon light making the Leaning Tower glow almost gold. There were crowds but somehow it didn’t matter; everyone seemed happy just being there, taking silly photos or lying on the grass near the cathedral. I climbed halfway up before chickening out (the stairs are steeper than they look) but even from below, seeing all those centuries stacked up is wild. We grabbed souvenirs, then back into the car as dusk settled over Tuscany.

What’s included

Your day includes hotel pickup and drop-off from Florence by luxury Mercedes vehicle with air conditioning and WiFi onboard.
flexible sightseeing time in Siena, San Gimignano, and Pisa.
entry to Siena Cathedral.
optional access to climb Pisa’s Leaning Tower if selected.
bottled water throughout.
commentary from your professional driver along scenic routes.
plus support from a dedicated office team before and during your trip so you can tweak plans as you go.

Good to know

Moderate physical levelStroller friendlyInfant seats availablePublic transport nearbyNot for heart conditionsNot for back problemsInfants must sit on laps

Operated by Ciao Florence Tours Srl