Insider's itinerary 2018

This marvellous tour unlocks the secrets of Tuscany, Italy's most beautiful region.

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Day 1

Your tour starts with a guided tour through the Florence, starting from your hotel overlooking the Arno River, crossing the Ponte Vecchio and exploring the historic centre of Italy’s most beautiful city.  After returning to the hotel, we’ll have an aperitivo and then dinner in a charming family-run osteria.   Dinner

Day 2:

The day starts with a walk and a guided visit of Florence’s famous produce market, the Mercato Centrale.  This is followed by a cooking lesson and lunch in the newly appointed kitchens above the market.  After lunch, the afternoon is free to explore or do some shopping on your own.  In the evening, we regroup at the hotel to visit the private gardens of one of Florence’s historic families, founded in the 16th century: seventeen acres hidden in the heart of Florence, it is the largest privately-owned garden in Europe situated within city boundaries.  We will be accompanied by a member of the family, who still live here.  After an aperitivo at the gardens, the evening is free.   Breakfast and lunch

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Day 3:

Today you will come face-to-face with some of the greatest works of Western art, starting with a guided visit to the Uffizi gallery, to see masterpieces by Leonardo da Vinci, Michelangelo, Botticelli, Giotto etc.  We then go to the Accademia to get up close to Florence’s most famous citizen, Michelangelo’s extraordinary statue of David.  On the way to the Accademia, you will stop for a demonstration of gelato making at the city’s best gelataria.  After a light lunch (wood-fired piazza) we will have the rare privilege of a private visit to one of the great Florentine foundations: the Opificio delle Pietre Dure, dedicated to the restoration of Florentine art since being founded by the Medici in 1588.  In the evening, we will have dinner at one of Florence’s culinary institution, operating since 1979.   Breakfast, lunch and dinner.

Day 4:

To today we leave Florence and head south to visit its eternal rival Siena, ‘the best preserved Medieval city in Europe’.  Anna will take you on a tour of the centre of this beautiful city, stopping on the way to visit a panforte maker (a delicious cross between fruitcake, candy, and honey cakes, a most Sienese treat).  You will have the late morning and early afternoon free to explore the town and have some lunch.  We then drive south to the Val d’Orcia (the Orcia River Valley) an area as famous for its rolling hills, wheat fields dotted with red brick farmhouses, stands of deep green cypress pines and endless views, as it is famous for its wines and food.  After checking into your hotel, you will be taken on a walk through San Quirico d’Orcia and then have dinner.   Breakfast and dinner

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Day 5:

This morning we drive to lovely Montalcino, a pretty town perched on a hill high above the valley and home of Italy’s finest red wine, Brunello di Montalcino.  After a visit to the town, Anna will take you on a lovely two-hour walk through forest and vineyards to a 12th castle that is owned by one Italy’s most important contemporary artists and produces some of the finest Brunello.  After a visit to the castle we will have a degustation and a light lunch in the castle grounds.  In the afternoon, we return to our base via a 14th century Benedictine, Tuscany’s grandest monastery, once known as the Monastery of the Moon for its splendid isolation.  The monastery contains a wonderful fresco cycle by the great Renaissance painter Luca Signorelli.  Back in San Quirico the evening is free.   Breakfast and lunch

Day 6:

This morning we drive south to the nearby town of Montepulciano, Tuscany’s highest hill-town, which dates from pre-Roman times.  This morning you will have a cooking lessons in the kitchens of one of the areas best restaurants.  In the afternoon we visit the beautiful town of Pienza, stopping at one of the valleys celebrated pecorino cheese producers before returning to our base.  In the evening we’ll have our farewell dinner in one of towns excellent restaurants.   Breakfast, lunch and dinner

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Day 7:

After breakfast, we’ll be transferred to Chiusi railway station, 30 minutes away, which has regular connections to Rome and Florence.  Breakfast.

Interested in the An Insider's tour of Tuscany: Florence, Siena, Val d'Orcia Guided Tour?

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Insider's tour of Tuscany 2018

  • Tour Lead

    Anna Sagaria

  • Tour Dates

    3 September to 9 September, 2018

  • Tour Size
    7 to 15 people
  • Tour Cost


    per person
  • 6 nights’ accommodation (see the itinerary for details) in boutique hotels
  • All breakfast, and all lunches and dinners listed in the itinerary
  • All transfers during the tours and all paid admissions during the tour
  • 5 guided tours (Florence markets, Uffizi, Accademia, gardens, Opifico, Signorelli)
  • 5 town tours:  Florence, Siena, Montalcino, Montepulciaon and Pienza
  • 2 cooking lessons (Florence and Montepulciano)
  • Gelato and panforte demonstrations; wine degustation; cheese producer
  • All taxes and service charges at the hotels and restaurants as well as all gratuities during the tour



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