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Montepulciano, Pienza & Montalcino Day Tour From Rome

City Tours

From the Port of Rome To Tuscany Day Trips
Montepulciano, Pienza & Montalcino Day Tour From Rome
Code : RM19
Type : Private

Duration : 11 Hours

Price tag Starting From:
*81.25 €
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Adults (15 - 64)
Kids (4 - 14)
Senior > 64
Infant (0 - 3)


Get ready for a wine and cheese extravaganza in Montepulciano, Pienza and Montalcino that will make your day trip from Rome truly delectable!  

Features of this day trip to Montepulciano, Pienza & Montalcino from Rome:

  • Pickup/drop-off at your Rome lodgings
  • Air-conditioned vehicle
  • Medieval architecture
  • Handsome churches, public buildings, and piazzas
  • Picturesque countryside, spectacular views
  • Fantastic local food products
  • Wine tastings in Montepulciano and Montalcino
  • Cheese tasting in Pienza
  • Great shopping

Our excursion begins with a scenic drive through Lazio and the Tuscan countryside with your private driver.


Nestled in one of the most beautiful parts of Tuscany, between the Val d’Orcia and the Val di Chiana, is the hilltop town of MontepulcianoA perfect Medieval village and “16th Century jewel”, it is surrounded by vineyards, rolling landscapes and thermal springs.

Stroll the narrow streets lined with elegant palazzi that surround the visitor with a warm glow of brick and chestnut tones.  If it’s near the hour head towards the Torre del Pulcinella, and you’ll get to see the puppet a character from 17th century Neapolitan commedia dell'arte striking the bell to mark the time on top of the clock tower.

Like Montalcino, Montepulciano is known for its red wine, Vino Nobile being the most acclaimed.


A small farming community until the beginning of the 15th century, Pienza’s future changed dramatically thanks to the birth of Aeneas Sylvius Piccolomini, who became a great humanist scholar and, later, Pope Pius II.  Piccolomini was the first to implement the humanist concept of urban design, basically brilliant town-planning techniques that turned his hometown into a little jewel of the Renaissance.

Today Pienza is best known for its cheese, especially pecorino (sheep’s milk) cheese.  If you aren’t hungry when you arrive you will be when you get a whiff of the marvelous cheesy smells wafting from the shops.


After driving across enchanting hills dotted with vineyards and cypress, you’ll arrive in Montalcino. This lovely Medieval town owes its wealth and fame to the wisdom of winegrowers who have created and promoted one of the most famous Italian wines in the world: Brunello di Montalcino.

Even though Montalcino’s wine is famous, it is the fortress that immediately catches the attention of the tourist upon arriving. This beautiful and imposing structure, constructed in 1361, will make you exclaim, “Now that’s a castle!”  The Rocca is wonderfully preserved and you can walk around the interior (for free even). 

As you stroll around the streets that haven’t changed in many centuries, you’ll enjoy the many architectural points of interest, mostly churches in a variety of styles:

  • The Cathedral (Neoclassical style),
  • The church of St. Egidio (simple Romanesque facade)
  • St. Agostino (14th-century frescoes)
  • St. Francis (beautiful cloisters)

Priori Palace, with its skinny clock tower and decorated with coats of arms is another good place to get some great Kodak moments.

As you tour the town why not taste some wine?  Eat, drink and be merry; you have a driver!


  • Private vehicle
  • English speaking driver-guide at your service for 11 hours
  • Pick-up and drop off right at your accommodation in Rome.
  • Personalized itinerary customizable with your driver whenever possible
  • Live commentaries and explanations on board
  • Gas, toll and parking fees


  • Tickets and guides, if not specified to be part of the tour package, are an extra cost to be arranged with the office.
  • Lunch
  • Gratuities


  • Entrance fees are not included.
  • The cost of wine and cheese tastings is not included.

Meeting Point

  • Your driver will be ready to wait for you at the lobby of your hotel or outside your apartment in Rome. Please look for your driver and if you are not able to find him, please don’t leave but call the office ASAP. If you think you will be late for any reason, we kindly ask you to contact the office ASAP.


1. Is this tour private?

The tour is private, just for your party.

2. Is the driver also a guide?

Our English-speaking drivers are NOT licensed guides. In order to provide you with the best-in-class service, our English speaking driving guides have been trained to offer our clients a nice overview with information regarding the major highlights avoiding the expensive charges of hiring a private guide. Due to strict Italian laws & regulations that protect officially licensed guides, our driving guides can comment and explain the sights only from inside the vehicle but are not allowed to do so once they are outside the vehicle. They are regularly licensed instead to chauffeur the public. We highly recommend that you never book with any touring company that does not make this clear.

3. Does the driver go with us inside the monuments?

No, only a licensed guide is authorized to accompany you during the visit of sights. Our driver will drop you off close to the sights but will stay with the vehicle for the duration of your visit.

4. Does this tour include lunch and admission fees to sites? Can we do wine & cheese tasting?

Tickets and lunch are not included in the rate. On request, we can make arrangements for wine and cheese tasting at an extra cost. Please contact our office for pricing and reservations.

5. What is the duration of the tour?

The duration of this service is 11 hours including pick up and drop off at your hotel in Rome.

6. Is the itinerary flexible?

Our itineraries are completely flexible, and we will be happy to operate any changes to the original itinerary (within reason). Please contact our office with all the requests you may have so that we can better organize your day.

7. Is gratuity included in the price?

Tips are never included in our quotes. We think that a tip shouldn’t be included in the rate otherwise it would be a tax!!! Once in Italy do not feel as though you have to tip everyone because someone told you to. Tip only if you really liked the service. Tips are generally: 10% not bad 15 % great 20 % best tour in my life. Please report any abuse.

Cancellation Policy

There will be a full charge for bookings canceled with less than 72-hour notice for any service required. In this case, a full charge will be made on your credit card. If you miss your flight or if your airline decides to cancel the flight due to bad weather or if your flight is directed to another airport on arrival, please advise us on time (as soon as you know) or a full charge will be made.

Please give us enough time so we can accept other reservations and allocate them to our chauffeurs. If the ship does not make it to the pier for bad weather, you will not be considered responsible so NO CHARGE will be made to your credit card. A full charge will be made for a no-show-up.

Only pre-purchased skip-the-line tickets (if requested) are not refundable under the circumstance and will be charged to your card.

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