Castello delle Serre

Living The Dream Tour


Day 1

The journey will take us to San Gimignano. Famous for its towers, San Gimignano is one of the best-preserved medieval towns in Tuscany. When seen from a distance it actually has a skyline to admire. The wealth that saffron cultivation brought to this area in the medieval ages contributed to the urban development of over 70 towers, only 16 of which still stand today. You may decide to climb up one to admire the view or indulge in some shopping in one of the many fine ceramic shops or art galleries the village is filled with. Afterwards, we will depart for a tour, lunch and wine tasting will be at our first winery. We will then continue to the luxurious Castello delle Serre, our home for the next five nights. Enjoy your welcome dinner prepared by the owners.

Day 2

The Best of Siena.  Siena has not changed much since its heyday during the medieval ages. In complete contrast with its arch-rival Florence, Siena is a maze of brickwork and narrow, romantic alleyways. Here we will meet with an authorized local guide to tour the Duomo, Piazza del Campo, San Domenico and much more. Next, lunch at a one of our favorite local restaurants and then free time in the afternoon to shop or just wander around on your own.  Return in time for a historic tour of the castle before enjoying a casual dinner here in our village.

Day 3

Depart for the Chianti. Visit the charming village(s) and pass through a land enchanted by castles and monasteries. We will then proceed to a very special winery, and learn about one man’s quest to make internationally renowned wines in the Chianti Classico. Lunch and tasting with a tour of the estate and cellars. Today’s tour will be led by Castello delle Serre. We will have an afternoon pit stop at the Castello to freshen up before departing for a special dinner at a friend’s restaurant.

Day 4

In the morning, we will depart for Assisi and enjoy a guided tour of the Basilica of Saint Francis with its beautiful frescos by Cimabue, Giotto and Lorenzini. Lunch will follow. In the afternoon, we will visit Cortona, a town of Etruscan origin, which clings to a hill just beyond Lago Trasimeno. This is the setting for Frances Mayes’ novel (later made into a movie) “Under the Tuscan Sun”. The road leading up to the town is spotted with olive groves, monumental churches, monasteries, convents, while the town itself is filled with steep alleyways, artsy shops, and open-air cafés. Today’s tour will be led by a special guest tour director and local guides. Finally, enjoy dinner back at the Castello.

Day 5

In the morning, we will depart for Pienza, Italy’s finest example of Renaissance architecture and now known mostly for the best Pecorino on earth. Pecorino is a pungent sheep’s cheese that is Pienza’s specialty. After walking through the village, a Unesco World Heritage site, we will then proceed to Montalcino, home of the famous Brunello di Montalcino wine, in time for lunch. Brunello winery visit in the afternoon.  Today’s tour will be led by Castello delle Serre. We will then go to a local farm to table restaurant for a farewell dinner.

Day 6

Return transportation to Florence in the morning. All departures at the same time.



  • Accommodations at Castello delle Serre 5 night stay.  If wishing to extend your stay beyond the tour a discounted room rate will be provided.
  • Bus transportation to/from Florence (with the group as a whole) and including the entire itinerary including all toll roads, entry permits, and parking fees
  • 5 breakfasts, 4 lunches & 5 dinners
  • Wine included in all the meals provided
  • Tour escort throughout the trip
  • Admission fees for city sight seeing, winery tours, wine tastings and cheese tasting.

** We reserve the right to make some alterations or changes to this itinerary. **

Subject to minimum of 12 participants, maximum 18 participants. Subject to availabilty, direct bookings only. Please email for rates and room categories available.

To reserve your place on our tour, please send an email to: