Private tour to Montalcino, Pienza and Montepulciano
Turn the postcard views into reality! Dive into Tuscany's countryside and explore 3 medieval villages: Montalcino, Pienza and Montepulciano!
from €700≈ $812 · £600Other currencies at today’s rate — you are charged in euro
- Location:
- Florence
- Duration:
- 10 hours
- Language:
- English
- Tour type:
- Private tour
- Group:
- Your party only
- Free cancellation:
- Up to 24 hrs
- Ticket:
- E-ticket on your phone
- We collect you where you are staying
Why you will remember it
- Private is just for you! Top safety, comfort, privacy and flexibility
- Admire unique scenarios of the stunning Tuscan countryside , visit 3 medieval villages
- Visit the charming medieval town of Montalcino
- Visit Pienza, touchstone of Renaissance urbanism and Unesco site
- Visit the hilltop village of Montepulciano
- Fall in love with Tuscany driving through postcard views
The itinerary
Explore 3 medieval Tuscan towns: Montalcino, Pienza and Montepulciano
Turn the postcard views into reality! A whole day to discover the stunning Tuscan countryside South of Siena. Dive into the picturesque landscape and beautiful medieval villages.
MONTALCINO
After passing Siena, continue through the ‘Crete Senesi’ beautiful area to reach the famous wine town Montalcino. The scenery is breathtaking here – cypress trees, fields and livestock with extraordinary combinations of green, gray and brown landscapes.
Brunello wine
The famous Brunello wine is produced here using the local Sangiovese grapes. Every activity in this town revolves around wine production and rightly so. Brunello is one of the finest and most prestigious wines produced in the whole world!
Inside Montalcino’s imposing fortress, visit ‘Enoteca La Fortezza’, a unique wine shop with a large variety of local Brunello wine.
Wander in Montalcino
Have a walk in the beautiful village, admire Piazza del Popolo, Palazzo dei Priori. Visit the churches of Sant’Agostino and Sant’Egidio and the beautiful Cathedral.
PIENZA
Stop in Pienza, a charming Tuscan town recognized by UNESCO as a worldwide cultural and natural patrimony site.
Birthplace of a pope
The history of Pienza is tied to that of Pope Pio II, born in Pienza on the 18th of October 1405 with the name of Enea Silvio Piccolomini. He was a great Humanist and wanted to transform his birth town from a small medieval hamlet into a Renaissance-style papal residence. Many of the palaces you see today in Pienza are from that time.
Walk in the Street of Love!
Get to the top of its hilltop location, admire the unforgettable view over the most picturesque valley, Val D’Orcia and the surrounding countryside. The streets in Pienza have curious names such as ‘Via dell’Amore, del Bacio, della Fortuna’ (the Street of Love, of Kiss, of Luck!).
Artisan shops and pecorino cheese
Shop here, the streets are lined with small shops selling local crafts and regional specialties such as delicious ‘pecorino di Pienza’ wine and many shops are willing to give out some samples of their fare to taste.
MONTEPULCIANO
Last stop of your Tuscan day: Montepulciano, located in one of the most breathtaking areas in Tuscany.
Culture and wine
This interesting wine town was entirely built on volcanic rock and stands about 600 meters above sea level. Today Montepulciano is known for its very impressive Renaissance buildings, its beautiful churches and especially for its ‘Vino Nobile’ (noble wine), one of the most distinguished Italian wines in the world.
Discover Montepulciano
The town developed on a steep hill between the gates of Porta al Prato and Piazza Grande and is crisscrossed by short and narrow streets and alleys. There is plenty of sightseeing here and the Cathedral is worth a visit.
Don’t miss Palazzo Comunale, the temple of Madonna of San Biagio and the church dedicated to Saint Augustine.
A relaxing drive back to your accommodation in Florence concludes your private day in Montalcino, Pienza and Montepulciano.
Private tour — everything you need to know
Included:
- Private service: your party will be the only one in the vehicle
- Free Cancellation up to 24 hours prior departure
- Pick up and drop off directly at your accommodation in Florence
- Knowledgeable English-speaking driver to lead you through the experience
- Transport with fully equipped Mercedes vehicle, free Wi-Fi and fresh bottled water
- Free time to visit Montalcino at your own pace
- Free time to visit Pienza at your own pace
- Free time to visit Montepulciano at your own pace
- All taxes, tolls and gasoline
- No hidden costs
Not Included:
- Entrance fees (if applicable)
- Meals
Optional:
- Gratuities
- Extra hours to extend your day (Euro 90.00 per hour, per party)
Prices below are per party (not per person), vary depending on group size and are valid for pick up/drop off in Florence.
- Euro 700.00 – party of 1 person
- Euro 750.00 – party of 2 people
- Euro 800.00 – party of 3 people
- Euro 850.00 – party of 4 people
- Euro 900.00 – party of 5 people
- Euro 950.00 – party of 6 people
- Euro 1000.00 – party of 7 people
- Euro 1100.00 – party of 8 people
For different pick up/drop off locations, larger parties (9 or more people) or customized itineraries, please Contact us for alternative options for an estimate.
Tour type: private, your party will be the only one in the vehicle
Language: the driver is English-speaking
Vehicle: Mercedes sedan or van, depending on your party size
Activity level: easy
Accessibility: the experience can accommodate people with reduced mobility and foldable wheelchair/scooters users, if advised at the time of booking
Friendly cancellation policy: full refund for cancellations up to 24 hours prior to the departure time
Book With Confidence & Travel Safe: this tour is covered by our special Book with confidence and travel safe policy
Departure/Return point: your accommodation in Florence
Departure time: customize it to suit your travel needs
Service duration: The price includes up to 8 hours (i.e. 9:00am pick up – 6:00pm drop off). If you’d like to extend your day you can check availability directly with your driver.
Meeting instructions:
Hotel: your driver will look for you in the lobby of your hotel.
Private apartment: meet your driver close to the main door, in the street.
Any different meeting instructions will be notified on your confirmation voucher.
- 9:00am – Depart from your accommodation in Florence
- 10:45am – Arrive in Montalcino
- 10:45am to 12:00pm – free time to visit Montalcino, at your own pace
- 12:30pm to 2:30pm – free time to visit Pienza, at your own pace with time for lunch (if desired)
- 2:45pm to 4:45pm – free time to visit Montepulciano, at your own pace
- 7:00pm – Arrive at your accommodation in Florence
Please note: the schedule is to give an idea about distances, driving and sightseeing time.
This tour can be completely customized to suit your travel needs! You may be an expert wine lover and want to spend more time tasting wines. Or you may not drink alcohol and want to admire the amazing Tuscan landscapes.
Whatever your interests are we can build the perfect itinerary. Let us simply know your preferences at the time of booking or tell your driver at the beginning of the day.
What our guests actually say
Every review below is public on the platform it came from.
My father and I had a wonderful day with Donatello who showed us so many beautiful places in the countryside of Tuscany. We had the best time and appreciated Donatello's knowledge of the places we visited. I would fully recommend this tour! Everything was perfect!
Still not sure?
Ask us anything
A date that is not there, a pickup somewhere else, six people and a pushchair — if something does not fit, tell us and we will work it out. A person answers, usually within a few hours.
Have questions? Let’s chat!
Meet our native English-speaking experts, Violeta and Carrie. A different pick-up time, a second vehicle for a larger family, a licensed guide, a winery to add, a wheelchair to fit in the boot, a drop-off at the airport on your last day — tell them what your day needs to look like and they will build it.
Not sure yet?
Tell us what your day should look like
Private tours are built, not booked from a calendar. Send us the details and a real person answers — usually within a few hours.