The Heart of Tuscany Tour - September 24 to October 3, 2023

The Heart of Tuscany Tour - September 24 to October 3, 2023

Siena, San Gimignano, Montepulciano, Pienza, Montalcino  & Florence

Daily Itinerary


  • Italy's capital city, majestic Rome
  • Beautiful medieval Siena
  • The delightful hills of the Chianti countryside
  • Scenic towns of Southern Tuscany
  • Italian cooking demonstration
  • Wine tastings at top wine producers
  • Pecorino cheese tasting at local farm
  • Superb authentic Tuscan dinners
  • The city of Florence, with a visit to
    Michelangelo’s David
  • Small group of no more than 16


This tour features the colors, tastes and aromas of one of Italy's most loved regions. The experience kicks off in Rome with an aperitif at the private and elegant residence of Discover my Italy's friend, Margherita. After that it's nine days of immersion into the rich culture, cuisine and beauty of Tuscany as you visit the charming towns of Siena, Monterigioni, Castellina in Chianti, San Gimignano, Pienza, Montepulciano, Montalcino and of course, the city of Florence. There will be fun and enriching activities - olive oil tastings, a Tuscan cooking demonstration, a visit to a family-owned Pecorino cheese manufacturer, to name just a few. You will also sample and learn about the renowned Chianti Classico, Vino Nobile and Brunello wines. At the Abbey of Sant'Antimo, we will leave our fast-paced world behind and be immersed in the monk's sacred Gregorian chants. The "Heart of Tuscany Tour" is an exceptional opportunity to experience the best of Italian culture and life.

The Heart of Tuscany Tour - Day by Day Itinerary

Departure from the United States

Thursday, September 24

Day 1 - Rome

Friday, September 25

Morning: Arrive in Rome and check in for one night to your four-star hotel in the heart of the city.

Afternoon: Free time to explore Italy’s capital on your own. Private guided tours are available upon request. Options include Ancient Rome, the Vatican or Borghese Galleria.

Evening: Enjoy a welcome reception filled with italian flavors and style at the private residence of Giovanna's friend Margherita.

Day 2 - Siena

Saturday, September 26

Morning: Depart for the town of Siena, a charming medieval Gothic town in the center of Tuscany. Check-in for three nights in our elegant hotel.

Afternoon: Tuscan group lunch at a local trattoria followed by an Orientation Walk of Siena’s Center with local guide. We will reach the famous Piazza del Campo, which is shaped like a shell and hosts Siena’s famous horse race every year, the Palio. Your guide will also share entertaining stories on Siena’s medieval traditions and their role in contemporary life.

Evening: Dinner on your own.

Day 3 - The Chianti region

Sunday, September 27

Morning: Depart on an excursion to the Chianti region which lies South of Florence and North of Siena. Our tour begins with a visit to charming Monteriggioni, considered one of the best preserved medieval hamlets in all of Italy. After exploring Monteriggioni we will head towards the Etruscan hill village of Castellina in Chianti.

Afternoon: Enjoy a Chianti Classico wine tasting and light lunch at an organic farm and family-owned estate. We will finish the afternoon in Greve, the main town of the Chianti Region, for a leisurely stroll and free time for shopping in the main square before returning to Siena.

Evening: Dinner on your own.

Day 4 - Siena

Monday, September 28

Morning: Walking tour of Siena’s Center with licensed guide, Stefania. Highlights of the tour include the magnificent Cathedral and its colored bands of marble dating back to the 12th century and the impressive Palazzo Pubblico with its beautiful frescos.

Afternoon: At leisure. Free time to shop, relax of explore Siena on your own.

Evening: Group Tuscan dinner at a local Trattoria

Day 5 - San Gimignano & Bonconvento

Tuesday, September 29

Morning: Depart Siena to indulge in Tuscany’s countryside. En-route we will visit the UNESCO World Heritage Site of San Gimignano, known as the town of towers. Our tour will include a visit to the Collegiata Church, with its internal walls completely covered by beautiful frescos from the 13th to the 15th century.

Afternoon: Arrival and check-in for three nights at our fabulous country residence in the Bonconvento area of Southern Tuscany. The estate is surrounded by 85 acres of vineyards and olive groves. Alberto, the owner of this beautiful property, will welcome us and share his passion for Southern Tuscany. After a tour of the winery we will gather in the kitchen for a fun Tuscan cooking demonstration.

Evening: We will enjoy the traditional Tuscan meal that we prepared together.

Day 6 - Sant'Antimo & Montalcino

Wednesday, September 30

Morning: Will start the day by visiting the delightful town of San Quirico d’Orcia followed by a visit to a local olive oil mill. Depart for the beautiful 9th century abbey of Sant’Antimo where we’ll hear the monks’ Gregorian chants. The monastery is located in a picturesque setting, a timeless landscape of fields and wooded hills.

Afternoon: Next is a visit to the town of Montalcino. Montalcino sits on a hill in the heart of vineyards producing Brunello wine, considered to be one of Italy’s most prestigious wines. Free time for lunch and to explore the town's narrow winding streets filled with artisan food and wine shops. We will end our afternoon with a tour of a renowned winery followed by a wine tasting.

Evening: A superb authentic Tuscan dinner awaits you at the villa.

Day 7 - Pienza & Montepulciano

Thursday, September 31

Morning: We will pass through the Crete Senese (Siena clay hills) to reach our first destination, the renaissance town of Pienza. Pienza is known as the “ideal city” and offers stunning views of Southern Tuscany’s countryside, the Val D’Orcia.

Afternoon: Some of the best Pecorino cheese in Italy is produced in the Pienza area. We will visit a family-run Pecorino cheese farm followed by a cheese tasting and light lunch in the company of the farm’s owner. Our next stop is the region’s highest hilltop town, Montepulciano, home of the Vino Nobile. Our guide, Stefania, will take us through Piazza Grande, Renaissance palaces and ancient alleys. We will also tour the amazing Cantina Ricci, an old winery whose cellars are carved out of tufa stone. Here we’ll have a chance to taste the famous Vino Nobile di Montepulciano.

Evening: A superb authentic Tuscan dinner awaits you at the villa.

Day 8 - Florence

Friday, October 1

Morning: Leaving the countryside our destination will be Tuscany’s capital city, Florence, the birthplace of the Renaissance.

Afternoon: Check-in for two nights at our four-star hotel, then meet with our local guide, Elena. Elena will take us on an historical and architectural walking tour of Florence's center, covering the Piazza del Duomo, Piazza della Signoria and Ponte Vecchio. The tour will end with a visit to the Accademia Museum to see the famous Michelangelo’s David.

Evening: Dinner on your own.

Day 9 - Florence

Saturday, October 2

Morning: Guided tour of the Uffizi Gallery, one of the oldest and most famous art museums in the world with a great collection of Renaissance art. Admire Botticelli’s well known masterpieces, the 'Birth of Venus' and “Primavera”. You will also enjoy works by Giotto, Leonardo da Vinci, Perugino, Michelangelo, Raphael, Titian and Vasari.

Afternoon: Spend the rest of the day exploring Florence on your own and indulging in shopping and beautiful sights.

Evening: Farewell dinner at an elegant Florentine restaurant.

Day 10 - Early morning transfer to the Florence airport.
End of tour.

Sunday, October 3

Itinerary specifics subject to change.

The Heart of Tuscany Tour - Pricing

Your tour price includes:

• Beautiful elegant hotel accommodations as follows;

  • 1 night 4-star hotel in Rome
  • 3 nights 4-star hotel in Siena
  • 3 nights in a country residence in Boncovento
  • 2 nights 4-star hotel in Florence

• Breakfast daily

• Private transportation through out the itinerary - Not including airport tranfers -

• 1 Welcome dinner reception in a private residence in Rome

• 1 Welcome lunch in Siena

• 2 Country light lunches

• 3 Wine tasting presentations with winemakers/owners

• 4 Exceptional dinners with important wines (1 in Siena and 3 in the Tuscan countryside)

• 1 Farewell dinner in Florence

• Visit to cheese factory with Cheese Tasting

• Guided tours of: Siena - the Chianti region - San Gimignano - Pienza, Montepulciano -
   San Quirico d'Orcia - Montalcino - Florence

• All museum entrance fees

• All local taxes

Not Included:

• Flights

• Airport Transfers

• Meals and drinks unless listed

• Personal expenses such as telephone, minibar, etc

• Gratuities for guides and drivers

• Travel Insurance (strongly recommended)


Tour Cost based on double occupancy

10 days/9 nights The Heart of Tuscany ...................... $TBA

Single Supplement......................................................+ $TBA


All aspects of the tour will be coordinated by Giovanna Chiti of Discover my Italy.


Rome, Saint Peter's Balica

Siena, Piazza del Campo

Chianti's countryside

Shopping in Siena

San Gimignano

Cooking Class

Medieval Palio flag



Piazza Grande, Montepulciano

Florence's Duomo

Florence, Ponte Vecchio

Michelangelo’s David

Terrace view from our elegant country residence

Out-Of-The-Ordinary Travel Experience





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