Nancy Aiello exclusive heart of Tuscany day trip blends art, history and amazing landscapes with delicious food and wines. Travel the heart of Tuscany dotted with cypress trees, and vineyards, fortified castles and hilltop towns each telling a fascinating history. Experience the most scenic Tuscan routes and the quaintest villages which remain as they were in the Middle age. Visit vineyards and wine cellars. Taste exquisite Tuscan wines. Meet the local producers and learn about the passion that goes into making their wine. This exclusive heart of Tuscany day trip captures the sights, sounds and tastes of Val d’Orcia. Avenues of cypresses, rows of vineyards, olive groves, golden wheat fields, charming farmhouses and monasteries that have withstood the test of time are just some of the elements of the harmonious landscapes of Val d’Orcia which inspired famous painters. Enjoy privileged, personalized attention from your expert driver/guide. Your personable driver/guide introduces you to the Val d’Orcia and the ageless atmosphere of the historical little towns of Montalcino, Pienza and Montepulciano with insider knowledge and enlightening anecdotes. This exclusive heart of Tuscany day trip ensures a personalized experience based on your interests with the utmost flexibility to explore at your own pace.

Montalcino located on the outskirts of Siena is a strikingly fortified medieval town with an imposing 14th century fortress. Montalcino is home to Tuscany most celebrated vineyards featuring diverse landscapes and world-renown Super Tuscan wines such as the famous red wine Brunello di Montalcino. The fortified medieval hilltop town of Montepulciano is home of the Vino Nobile obtained from the surrounding vineyards. Wine connoisseurs consider its Vino Nobile among Italy best. The small town of Pienza is a rare example of a Renaissance ideal town created by Pope Pius II who turned it into his papal summer court and now is listed by UNESCO as World Heritage Site. Piazza Pio II is the heart of Pienza lined with Renaissance buildings and home to the impressive Cathedral and Palazzo Piccolomini, which used to be the Pope residence. This square is also lined with shop where local artisans sell their savory truffles, fresh gelato, and Pienza most famous product, pecorino cheese! Contact us to experience Val D’Orcia and the remarkable historic towns of Montalcino, Pienza and Montepulciano with this exclusive heart of Tuscany day trip.

* Family Friendly
* Private Full-Day Chauffeured Trip
* Private Licensed Professional Driver/Guide
* Full Day Private Deluxe Vehicle
* Florence Hotel Pick Up and Drop Off
* Scenic Drive
* Val d’Orcia Top Attractions and Hidden Gems
* Best Photo Ops

Optional Upgrades to Enhance Your Private Excursion

Travel Tuscany in Comfort and Style by Mercedes Benz GL Class 4×4 Luxury SUV

ADD ON Private Mercedes Benz GL Class 4×4 Luxury SUV


This private guided Tuscany trip can departure from any Tuscan town.

For our guests comfort we only operate private tours by private cars and/or minivans which can get closer to the main points of interest than larger buses. According to Italian traffic regulations licensed minivans up to 8 passengers are considered equivalent to taxis therefore, can access all the restricted areas of each city center. Private cars and/or minivans can go and stop in front of sites and so the walking distance to be covered is minimum which allows us to maximize your precious holiday time reducing to zero the walking time otherwise required to go from the bus pick up/drop off point to the city centers and vice versa during the visit. This is a HUGE advantage especially when you visit Tuscany countryside where by using a bus passengers would be forced to walk long distances to just reach the city center from the drop off point and back for the pick up. This means a lot of saved time therefore, more sightseeing at relaxed pace within the same number of tour hours.

Baby seats are mandatory for infants, please request at time of booking.

Can I join a group tour?

Unfortunately this is not a service we offer. Nancy Aiello Tours specializes in individual and family private tours. Our private tours are exclusive to one booking party and we do not combine separate reservations to form small groups. Our private tours mean that you do not share your tour with anyone else. Your private tour is tailored to your individual needs and interests so everyone can ask questions and get the most from a new experience.

Which wineries will we visit?

There is no set schedule of wineries. Because the wine estates require reservations for a set time we take advantage of the best winery experiences available on that day.

Are tastings included in your private Tuscany day trip?

Tastings are NOT included in the price of this tour as they vary according to your interests. Each touring experience is unique which is why our private tours are personalized and not standard tours therefore, the cost of tastings, meals and drinks are not included. Prices will depend on your choice and requirements. You will pay the tastings on the day of your visit.

Do we stop for lunch during our private Tuscany excursion?

Yes. The duration of the tour includes time for breaks to grab a quick snack and/or lunch. Your private driver/guide would be happy to provide with suggestions for lunch to suit your tastes and budgets. The cost of the meal is NOT included in the price. Some people like to grab a quick pizza or a snack, and some people like to sit down for a nice relaxing Italian meal. You may take a break at any time during the tour upon request. Otherwise, breaks will be at our discretion.

Are your private vehicles licensed and insured?

Yes. All of our vehicles are officially licensed and insured.

Are your private vehicles non-smoking? Air conditioned?

Yes. All of our vehicles are non-smoking and air-conditioned.

Are tips included?

Tips are optional. Gratuity is not included and is left to individual discretion.


Private Tuscany Trips


Experience Tuscany your way. Our private guided Tuscany trips delve into art, history in an educational and fun way.

Private Florence Tours


Experience Florence your way. Our private guided Florence tours delve into art, history in an educational and fun way.

Private Rome Tours


Experience Rome your way. Our private guided Rome tours delve into art, history in an educational and fun way.


Private Vatican City Tours


Experience the Vatican your way. Our private guided Vatican City tours delve into art, history in an educational and fun way.

Private Venice City Tours


Experience Venice your way. Our private guided Venice tours delve into art, history in an educational and fun way.

Private Southern Italy Tours


Experience Naples and beyond your way. Our private guided Naples tours delve into Southern Italy art, history in an educational and fun way.


Experts in Inspired Tuscany Luxury Trips!


  • Tour Venice in 1 Day

    Ms Elisabetta was a fabulous guide and we all had a great time with her.

    Sally Rorke
  • Ancient Rome Wheelchair Accessible Tour

    Our experience with Nancy Aiello Tours was  easy to book, customer focused and well guided and we certainly would like to recommend the guide that we had. He lived up to our expectations and would like you to bring our special regards to him because of the excellent way he guided us.

    Frank van Asten
  • Family Tours in Italy

    I would be happy to put a review on TripAdvisor. Our overall experience couldn’t have been better. Ann was very helpful through the booking process, and very prompt in her response to my queries both before booking and before the first tour. We couldn’t have asked for a better tour guide in Cinzia. She was wonderfully engaging with our boys and was really able to capture their interest, especially in the more difficult Vatican Tour. My husband and I really learned a lot as well! It was especially great to have her for both tours, the continuity really helped. I would have no hesitation at all in recommending Nancy Aiello to my friends. I found you quite by accident when I was researching family tours in Italy. I believe you have a link on a website Ciaobambino? Thank you again for a delightful experience for my family.

    Reemah Sen
    New York, USA

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