When in Florence enjoy the best Siena San Gimignano day trip. Venture into the heart of Tuscany and travel back to the Middle Ages. Explore the medieval towns of Siena and San Gimignano UNESCO World Heritage Sites. Enjoy privileged, personalized attention from your expert driver/guide who shares inspiring and insightful stories that bring your destinations to life. This exclusive Siena San Gimignano trip offers discerning travelers and families with kids the chance to experience the essence of these historic towns in comfort and style. Start your exclusive Siena San Gimignano trip from Florence with an approx. 30 minute drive (traffic pending) in the comfort of a private deluxe vehicle. Enjoy the rolling Tuscan landscape of vineyards and cypresses en route to San Gimignano, the medieval Manhattan in the heart of Tuscany. During the scenic journey your personable driver/guide provides a comprehensive introduction to the city wonders and its haunting medieval history. San Gimignano, a tiny fortified hill town known as the City of Beautiful Towers looks frozen in medieval time. Children will adore the fairytale like towers, 13 only remain of the original 72 which reflect the power and prosperity of the city families. San Gimignano, Italy best preserved medieval town features Roman ruins and medieval architecture. You can feel history in the smooth cobblestones under your feet. The cobbled streets, the thick protective city walls and the remaining 13 towers are a fantastic experience for adults and children alike!

Proceed to Siena renowned for its striking architecture. Surrounded by olive groves and vineyards Sienna is an open air living museum brimming with some of Italy finest Gothic architecture. Siena was the richest city in Italy during the Middle Ages. Its architectural legacy is a testament to its former greatness. Siena, which competed with Florence was crushed by Florence and it took centuries for the city to recover. As a result much of the character of the old city remains including the original walls and the twisty streets. Curiosities and singular stories will let you experience the story of Siena and the way in which buildings were made. Learn how Siena rivalry with Florence shaped the city. Stroll through mysterious streets and narrow lanes where time seems to have stopped; it is here where history and legend meet! Discover the famous Cathedral. Explore Piazza del Campo site of the annual Palio Horse Race. Exclusive Siena San Gimignano trip is an informative yet engaging experience for adults and children alike. At the end of your exclusive Siena San Gimignano trip your personal driver/guide transfers you back to Florence. Contact us for an exclusive Siena San Gimignano 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
* Siena Top Attractions and Hidden Gems
* San Gimignano Top Attractions and Hidden Gems
* Best Photo Ops

Optional Upgrades to Enhance Your Private Day Trip

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 a smooth operation this itinerary may operate in reverse.

The tour sequence may vary. The time spent at certain venues may be expanded/reduced, and other brief stops may be added.

Siena Duomo closes on Sundays.

When entering churches always ensure that you dress appropriately, no shorts or sleeveless dresses. By not being properly attired you run into the risk of being denied entry.

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.

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 Journeys!


  • Private Rome Shore Excursion Rome Vatican City Day Tour

    All I can say is Thank You. The experience we had was nothing short of excellent.  It started with Rachel and her responding to all my needs.  As for our driver, Fabio, if this is the kind of drivers you employ, you’ll continue to have great success.  He was by far the best driver I’ve ever experienced and with all my travel, I’ve experienced many. Great job with Fabio. As for our tour guide, everyone and I mean everyone should be so lucky.  Her name was Lucia and all four of us felt not only did she possess unbelievable knowledge, we felt like she was family.  Her ability to manage us, the time we had and that we wanted to see was fantastic. We HIGHLY recommend Lucia to everyone. As I close, I feel these words fall short of what we experienced. To say we would recommend Nancy Aiello Tours would be an understatement, in fact, I’ve already recommended Nancy Aiello Tours, Fabio and Lucia to several friends planning a trip in the coming months.
    Thank you again, and feel free to use me as an endorsement at any time.

  • Under the Tuscan Sun Tour

    Andrea was waiting for us outside our BnB in Rome and took us on the most relaxing tour to Tuscany for our first day in Italy. The Wine vineyard was wonderful and very mom and pop. We requested to do a stop overs at a small town art site and Aiello Tours was very accommodating.
    Andrea spoke perfect english and noted to us on sites as we drove around. He gave us some history of the area during the day. He is an exceptional employee of Aiello Tours. We enjoyed every moment with him. Fantastico!! Thank you so much for a wonderful first day in Italy.

    Karen Valckx
    Calgary, Alberta Canada
  • Rome Vatican City Tour

    Dear Nancy Aiello Team,
    I had received very positive feed back from Mr Zhang Zhan Bo and his Chinese delegation, he is quite happy with everything except the price is on the high side.

    Eric Cheng

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