Tuscany, time of olives in October

  • Max Group: 8 people
  • Duration: 9 days/8 nights
  • Starting Point: Florence Airport or train station
  • Payment Method: Major credit cards are accepted


  • Olive harvest and tasting with the Tuscan Family in the field
  • Relax in ancient residences completely restored and managed by local families
  • Guided tours in Siena and Florence
  • Amazing landscapes outside mass tourism
  • Meet the Tuscan families and cook pasta altogether
  • Have your Appetizer on the top of the Florence roofs

What to bring

  • Comfortable clothes
  • Comfortable shoes
  • A jacket for the night
  • Swimsuit (for thermal baths)
  • Space for your souvenirs
  • A little umbrella (optional)


  • Van at your disposal for the whole trip
  • Tour leader for the whole trip
  • All breakfasts
  • 6 dinners
  • 1 lunch in the field during the olive harvest with the family
  • 8 nights in hotels and country estates
  • All described activities

Not Included

  • 2 dinners
  • 7 lunches
  • Souvenirs


Day 1
Arrive in Florence (Airport or train station) and transfer to the Countryside Estate Orgiaglia, in the middle of the olives fields. In the afternoon, we will have a cooking lesson with Umberta where we will learn how to cook homemade pasta and we will get to know each other...and then, if you are good cooks, we will eat your pasta for the first welcome dinner!
  • Orgiaglia
  • Included: Dinner in Orgiaglia
Day 2
We will visit the historical town, Volterra, with our favorite guide, Claudia, and we will learn why this amazing town was so important during the Roman era. In the afternoon, we will do a beautiful bike ride inside the Natural Park near Franco’s estate and we will discover a hidden castle. In the evening, we will have a good dinner with Franco and Umberta.
  • Orgiaglia
  • Included: Breakfast and Dinner in Orgiaglia
Day 3
We will visit Siena. Our favorite guide, Agnese, will explain to us this important town at the top of the hill. We will enter inside Siena's Cathedral, the most beautiful one that I have ever seen! During this period of the year, they will show us the floors (normally covered to preserve them) and we will enter a special part of the cathedral where few people can go: the inside roof. From the top we will have a unique point of view of the floors. In the evening we will have the last dinner with Franco and Umberta.
  • Orgiaglia
  • Included: Breakfast and Dinner in Orgiaglia
Day 4
We will visit San Gimignano and we will take part in a fun treasure hunt game, discovering the special medieval corners of this unique village with many old towers at the top of the hill. In the afternoon, we will head to the Val d’Orcia region. We will drive on the ancient Via Francigena route. This is a medieval pilgrim route, with unique corners and panoramic views. We will sleep inside the restored historical castle of “Spedaletto”, where the Pope Pio II and the king Carlo D’Angio also slept in the pass.
  • Grancia di Spedaletto
  • Included: Breakfast in Orgiaglia
Day 5
We will relax in the Etruscan thermal bath of Bagno Vignoni. This historical village has been known since the Etruscan era (before the Romans), because of the natural hot springs. In the afternoon, we will visit the lovely Renaissance Pienza, immersed inside the Tuscan countryside. And for dinner, Pizza for everybody!
  • Grancia di Spedaletto
  • Included: Breakfast in Spedaletto, Pizza Dinner in Pienza
Day 6
We will have a perfect wine tasting with the historical Biondi Santi family. This family invented the Brunello of Montalcino wine, a unique and excellent wine from this area and they will open their canteen for us. For the lunch time, we will stop at the fortified village Monteriggioni...you will love it! In the afternoon, we will drive to Prato, where you will sleep in the medieval tower of the town inside the historical center. Prato has a lot of history and few tourists, so you will have the opportunity to live the authentic life of a historical town.
  • Torre degli Ammannati
  • Included: Breakfast in Spedaletto
Day 7
We will visit the amazing Florence centre with our favorite guide, Antonella. We will enter the Uffizi Museum to admire impressive painters like Brunelleschi’s, Michelangelo’s... but save some energy for the night! We will have a lovely Appetizer on the roof of the historical library of Florence with a fantastic view of the Duomo! Only for locals like us!
  • Torre degli Ammannati
  • Included: Breakfast in Prato and Appetizer in Florence
Day 8
This will be the special day of your holiday because we will take part in the olive harvest with all my Tuscan family! We will visit my grandfather's field on Prato's hills and we will have a countryside picnic lunch there. In the evening we will visit the olive mill, where the local families like us, produce their olive oil for all the year. We will have a special dinner with my family and friends of the mill. We will toast some bread in the fireplace to taste the fresh olive oil we produce. That oil will be the best!
  • Torre degli Ammannati
  • Included: Breakfast in Prato, Lunch in the field and Dinner in the mill
Day 9
We will have a transfer service to bring you to Florence (at the Airport or at the train station). We will wave to you goodbye and we will thank you for having traveled with us!
  • Included: Breakfast in Prato
Tuscany multi day tour Italy


October is the season of the new olive oil, and the beautiful fall colors. It is time to relax outside the massive tourism and to take part of the family ritual of olive oil, enter into the Tuscan mill, smell the oil’s perfume and taste it directly from the mill. It is just what you have dreamed of Tuscany.


Franco and Umberta will welcome us to their ancient farm in the middle of the beautiful Tuscan countryside between Siena, Volterra and San Gimignano. We will certainly be regenerated after our daily explorations by their warm hospitality, authentic cuisine and Chianti wine. Friendship, good laughter and a great company will help us get away from all the stress – all in a magical atmosphere.

They will host us in their elegant, recently restored double rooms. You will be mesmerized by the traditionally looking rooms while at the same time everything is eco-friendly (the hot water comes from solar thermal plants).

Grancia di Spedaletto

Many important people, such as Carlo D’Angio and the Pope Pio II, rested at the Castle La Grancia di Spedaletto during their trip to Rome.

Nowadays, the Carletti family is the owner of the Castle and the farm. They will host us in their elegant double rooms for a few days in this peaceful and quiet place surrounded by 40 hectares of vineyards and olive oil trees.

Torre degli Ammannati

We will have the opportunity to live inside this perfectly restored middle age tower. We will enjoy the comfortable and elegant apartments with original architectural elements of the middle age. Laura and Piero, the owners of the tower, will welcome us to their special house, right in the historical center of Prato. Wood, stones, cotton and modern elements will make you feel at home with a warm and evocative atmosphere.


Children are more than welcome. For babies, it is better to have a stroller to put them in, so they can sleep when they feel tired. Children between the ages of 6 and 11 inclusively are permitted on this tour at the rate listed above. Children under the age of 6 are permitted to join this tour free of charge. Please inform us at the time of booking if you’ll be bringing a child.

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