Tuscany · Siena & San Gimignano · Hotel pickup
Siena and San Gimignano Day Trip from Florence.
A Siena and San Gimignano day trip from Florence — two medieval Tuscan jewels in one private day. Piazza del Campo, the Duomo of Siena, and the famous city of towers, with hotel pickup in a comfortable MPV.
DURATION
Approx. 8 hours
GROUP
2 to 6 people
LANGUAGES
English · IT · PT/ES on request
PACE
Private MPV · two cities
Starting at
€860
total · 2 people
About this journey
Two medieval jewels in one day.
A Siena and San Gimignano day trip from Florence is an unforgettable Tuscan experience — a private tour with exclusive transfer from your hotel that delivers two of Italy’s most beloved medieval cities in a single, well-paced day.
Our first destination is Siena, a city of unique charm and rich medieval tradition. Explore its UNESCO World Heritage historic centre, admire the imposing Piazza del Campo — the shell-shaped square where the famous Palio horse race still runs twice a year — and be enchanted by the magnificent Duomo of Siena, considered one of the most beautiful cathedrals in Italy.
We then continue to San Gimignano, the famous ‘city of towers’ where time seems to have stopped. Walk through its medieval alleyways, admire the skyline punctuated by historic stone towers, and try the award-winning gelato that has made the city known worldwide. A tour that combines art, history and unforgettable Tuscan flavours.
What you’ll experience
Medieval Siena, and the city of towers.
Hotel pickup in private MPV
We collect you directly from your hotel in Florence in a comfortable air-conditioned MPV. Chauffeur service — no train, no logistics, no rushing.
Piazza del Campo, Siena
The most famous square in Tuscany, shell-shaped and sloping toward the Palazzo Pubblico. Where the Palio horse race runs twice a year, and Sienese life happens daily.
The Duomo of Siena
One of Italy's most beautiful cathedrals — black and white striped marble, a façade of intricate sculpture, and an interior with floors and pulpits by Nicola Pisano and Donatello.
San Gimignano's medieval towers
The 'medieval Manhattan' — 14 surviving stone towers (out of 72 originally) marking the skyline of a town that time forgot. UNESCO World Heritage.
Award-winning gelato
San Gimignano is home to Gelateria Dondoli, multiple-time world gelato champion. We give you time to taste it properly — saffron, vernaccia wine, traditional flavours done perfectly.
Italian driver who speaks English
Your driver is Italian, fluent in English. Portuguese or Spanish-speaking driver available subject to availability — please request in advance.
The tour, step by step
How the tour unfolds.
A natural rhythm of the journey, adapted to the season, the weather and your interests.
Start
Hotel pickup in Florence
Your driver collects you directly from your hotel in central Florence at 9am (or another agreed time) in a private air-conditioned MPV.
+ 1 h
Drive south through Tuscany
The hour-long drive south through the Chianti hills. Cypress-lined roads, vineyards, medieval castles. The Tuscany you imagined, scrolling past your window.
+ 1.5 h
Arrival in Siena
We park near the historic centre. A walking introduction to one of Italy’s most atmospheric medieval cities — narrow streets, terracotta walls, the soft sound of Sienese dialect.
+ 2 h
Piazza del Campo & the Duomo
Time at Piazza del Campo, then to the Duomo with its striped marble façade. Your driver explains the Palio, the Sienese contradas (neighbourhoods), and the soul of the city.
+ 4 h
Free time for lunch in Siena
Time to wander the alleys, find a trattoria for a proper Sienese lunch — pici pasta, wild boar ragù, panforte. Your driver recommends where the locals eat, not the tourist traps.
+ 5 h
Drive to San Gimignano
The scenic 45-minute drive through Tuscan vineyards to San Gimignano. The first sight of the stone towers rising from the hills is unforgettable.
+ 6 h
Exploring San Gimignano
Walk through the medieval alleys, the main piazza, the views from the city walls. Time for the world-champion gelato at Gelateria Dondoli (yes, it’s worth the queue).
+ 8 h
Return to Florence
The drive back to Florence as the afternoon light turns golden over the Tuscan hills. Your driver returns you to your hotel — comfortable, unhurried, with two cities lived properly.
The details
What's included, what isn't.
Included
- Approximately 8 hours private day trip
- Hotel pickup and drop-off in Florence
- Private MPV with Italian driver (fluent in English)
- Visit to Siena (Piazza del Campo, Duomo, historic centre)
- Visit to San Gimignano (medieval towers, historic centre)
- Group size of 2 to 6 people (fully private)
- Full booking support
Not included
- Entry tickets to monuments (Duomo interior, museums)
- Meals and drinks (gelato in San Gimignano is essential, though)
- Personal expenses and gratuities
- Portuguese/Spanish-speaking driver (subject to availability)
- Travel insurance
Investment
A price for every group size.
2 people
€860
Total tour fee
Most intimate · fully private
4 people
€910
Total tour fee
Best value per person · perfect for couples or families
6 people
€970
Total tour fee
Maximum group size · private experience
Prices include the qualified English-speaking guide and curated route.
When we go
Upcoming dates.
Send us your preferred dates and we’ll confirm availability within a day.
Spring
Mar · Apr · May — daily
Available
Summer
Jun · Jul · Aug — daily
Available
Autumn
Sep · Oct · Nov — daily
Available
Winter
Dec · Jan · Feb — daily
Available
Group rates
Starting at €860 for 2 people
See notes
Custom
Private group, your dates
Inquire
Good to know
Travel notes.
Pricing by group size
€860 for 2 people · €910 for 4 people · €970 for 6 people. Total tour fee, not per person. Includes the MPV, driver, fuel and visits to both cities.
Portuguese/Spanish driver
Available subject to driver availability — please request in advance when booking and we’ll confirm. Additional fees may apply.
The Palio of Siena
If you travel on July 2nd or August 16th, the Palio horse race runs in Piazza del Campo. Magical but the city becomes very crowded — let us know if you’d like to plan around it.
Meeting point
Your hotel lobby in central Florence. Pickup outside the historic centre may incur additional fees — let us know your hotel when booking.
Why combine Siena and San Gimignano
Both are UNESCO sites and 45 minutes apart by road. Visiting them together makes for one of the most complete Tuscan days possible — a city, a medieval village, and the landscape in between.
What to wear
Comfortable walking shoes (cobblestones throughout). Light layers in spring and autumn. Sun protection essential in summer (Tuscan sun is intense).
Reserve your tour
Ready for medieval Tuscany?
Send us a note with your dates, group size and hotel name. We’ll reply within a day with your driver’s details and pickup time.
You might also love
