Explore Medici’s Tuscany
What a great opportunity to discover unique Medici sites, learn more about the family, and enjoy the best of Tuscany in a 3-day guided tour from Florence.


Rulers of Tuscany for three centuries, the Medici Family changed history and shaped the region of Tuscany as we see it today, making our Medici tour a must for anyone looking to explore Tuscany off the beaten track.
This 3-day tour will follow their footsteps and decipher the legacy that this powerful family has left in Tuscany.
This 3-day tour will also give you the opportunity to enjoy Tuscany with delicious wine tastings, interesting activities and amazing villages to visit.
- Pick up and drop off from Florence.
- Small intimate groups.
- Guaranteed departure every day.
- Fully escorted tour with a local professional driver.
Day one: Villa di Poggio a Caiano and Chianti
Your local expert and driver will pick you up directly from your hotel in Florence and take you to the Medici Villa in Poggio a Caiano as the first stop.
The Villa Medici in Poggio a Caiano, a little town in the province of Prato, is just one of the palaces and villas scattered across the land, and you can almost hear in its rooms and halls the ghostly footsteps of the dukes, duchesses, painters and courtesans who lived there centuries ago.
After the visit to the Medici Villa, the driver will take you to Greve in Chianti where you can enjoy a beautiful lunch on your own at the famous "piazza" before moving to one of the local wineries and taste some delicious Chianti Classico wine.
The day will finish at your new home - the local, cosy accommodation where you will stay for the next 2 nights.
Check your accommodation here
Day two: Montepulciano and Pienza

We will start the day with a visit to Montepulciano, a medieval village of Tuscany where the Medici family certainly left their mark.
In the 14th and 15th centuries, there was incredible power and wealth in Montepulciano from the noble families that lived there. It was in the 16th century, however, that the town reached its highest point of splendor under the rule of the extremely powerful Medici dynasty.
There are two main gates into the town - Porta al Prato and Porta delle Farine. Once you have passed through these you can instantly start exploring the little nooks and crannies of this place on your walking tour.
The Church of Sant' Agostino was designed by the artist Michelozzo who was working for the Medici family. There is also a fantastic Tower Clock and the home of the poet Poliziano who was under the patronage of Lorenzo de Medici.
In the afternoon, we will visit Pienza. Visitors should not miss the tiny hilltop village of Pienza, nestled in the Val d'Orcia between Montalcino to the east and the Montepulciano hills to the west.
Some of southern Tuscany's most beautiful landscapes unfold along this route, culminating in the view from Pienza itself.
On a less exalted note, it is also the home of a pecorino (sheep's milk) cheese known as cacio, whose flavour can range from extremely delicate to thumpingly strong and sometimes has peppercorns inserted into it for extra crunch. Cacio is sold in many of the town's small shops, alongside local wines, pici (the local pasta) and, best of all, and our particular recommendation for visitors a mixture of all three - pici con cacio e pepe (pasta with cheese and pepper) washed down with a glass of Montepulciano vino.
Day three: Livorno and Pisa
On the last day of the Medici tour, the local expert and driver will take you to Livorno where you can enjoy a lovely cruise tour through the city and visit the famous port of Livorno.
Dominating the Ligurian Sea, it has been a gateway to Italy for many centuries and one of the country's most important ports.
In the afternoon we will visit Pisa before coming back to Florence and finishing the walking tour. Here, some of the amazing location you can explore on your guided tour:
- Statue of Cosimo I dei Medici: The statue of Cosimo I dei Medici, commissioned by his son and successor Ferdinando I, stands in the Piazza dei Cavalieri in Pisa and is a lasting reminder of the Medici family's domination of Tuscany.
- Palazzo Vecchio dei Medici: The grand building built to house the Medici family in Pisa is now the headquarters of the town's prefettura (local authority)
- University of Pisa: It was under Lorenzo the Magnificent that the Palazzo della Sapienza ('The Palace of Wisdom') was begun in 1486, extending the existing 'Pisan Studium', or old university.
PRICES, DEPOSITS, AND PAYMENTS:
Price for this tour is $1590 USD per person. Single supplement: $150 USD.
Once we have checked your documentation (including your travel insurance), a 25% deposit of the overall tour cost is required.
No booking will be reserved until the deposit is received.
Balance of the payment will be due 30 days before starting the tour.
Deposits and balance of payments are accepted by bank transfer or credit card via PayPal (5% surcharge).
Payment of the deposit indicates an acceptance of all the conditions.
ARRIVAL AND DEPARTURE TIMES:
Departures-Guaranteed every day with a minimum of 2 guests
Starts/Ends in Florence.
Max 8 people.
Pick up at your hotel in Florence or train station– Click here for more information www.trenitalia.com.
Contact us if you need advice on reaching the pickup point.
TOUR GROUPS:
Our tour groups have been designed for a group of no more than 8 people per week to ensure that client needs and enjoyment are always our top priority.
INCLUDED IN TOUR COST:
- Private room in a 4-star Tuscan accommodation.
- Two continental breakfasts and two dinners at the farmhouse with a set menu
- Pick-up and drop off from your accommodation in Florence.
- Daily transfer with a comfortable vehicle from the farmhouse accommodation to the different locations of the tour and back (9 hours/day tour service).
- Professional local expert and driver (no licenced "tour guide")
- 3 days touring to itinerary locations.
- On arrival at each location: remain as a group with tour leaders or explore independently and re-group at a pre-arranged time and location.
- Wine tasting at each winery location with a visit to the cellars at selected vineyards/establishments.
WHAT IS NOT INCLUDED IN TOUR COST
All items not detailed in inclusions
Personal spending
All transfers other than to the local train station
- Airfares
- Airport taxes
- Travel insurance
- Entry fees to museums/galleries and other places wherever entry fees apply
- All lunches and meals not specifically listed above
- All personal expenditure
- Refer to the specific tour
- Licensed tour guided
OPTIONAL EXTRAS: Activities beyond the specified tours listed on this website are subject to additional costs.
HISTORICAL TOUR GUIDE. If you are interested to learn more about art and history of any city we can engage a professional local tour guide who can explain you deeply the history and the culture of this area. The price is $95,00 USD per person (min 2 people). Max 3 hours service. If you want to include the tour guide, please, let us know at least two weeks before the starting of the tour.
DINNER OUT WITH THE LOCAL: After each day tour, you can choose between having dinner at the farmhouse (included on the package) or going out to a family-run trattoria near the accommodation for a different traditional Tuscany food experience with the local guide. You can organize the dinner out directly to your local guide during the tour. The price for this extra service (pick-up and drop off) is $58,00 USD per person (minimum 2 pax). The price doesn't include the dinner out.