Highlights of Tuscany: 8 MAX Gourmet Food and Wine Package October 10-17 Back

Departs from : Florence

Duration : 7 days

Type : Private

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Price Per Person : EUR 1,642.00

Meals Included

Breakfasts : 6

Dinners : 2

Lunches : 1

Wine Tastings : 3

Cooking Lessons : 3


This is a unique 8 max participant tour that visits some of the most beautiful areas in Tuscany as well as Umbria which is the region next door. The tour departs from Rome with an option to extend the tour in Florence and covers the beautiful Orcia valley, Siena, Cortona, Arrezzo, Montepulciano and Montalcino as well as many different wine estates.wa  

It is a great option for those who want to experience the Tuscan wineries and the smaller areas of Tuscany without having to drive.

The accommodations are superb, and based in a lush valley, surrounded by the rolling hills of Tuscany.  

Most meals on this tour are included with wine!  

With your drive guide and personal assistant, you will be able to experience some of the most beautiful regions in Tuscany, visit the local artisans, wine makers and cheese-makers. 

Stay in an absolutely beautiful location, at the Borgo Tre Rose, in one of the most spectacular locations in Tuscany with a small group of max 8 participants! 



Day 1 : Rome - Tuscany: Welcome Dinner at the Estate

Where we visit : Montepulciano

Meeting Location : Villa

Description :

Our tour will depart this morning from Rome in a central location we will reveal upon booking the tour. If you want to join the tour, but you are not going to be coming from Rome, we can make arrangements for you to get to meet us at the estate. 

En-route from Rome this morning we will stop in the beautiful town of Orvieto, one of the Etruscan's most beautiful towns with one of the oldest wine cellars in Italy. Together with a local guide, we will experience the wine cellars here and this incredible town.

After visiting Orvieto, we will continue our journey north on the Auto-Strada del Sole to the estate, where you will have some time to relax and unwinde before our welcome dinner which will introduce us to some of the local Tuscany cuisine.

Welcome dinner at the Borgo Tre Rose Estate.

Overnight at the estate. 



Meals : Dinner

Day 2 : A Day at the Estate: Cooking Course & Wine Tastings

Where we visit : Tuscany

Description :

Today will be a day dedicated to enjoying the best of the Tuscan wines and learning about what makes the Tuscan food so tasty,

We will experience over the course of the day, several different types of Olive Oil, various wine and experience a cooking course  

The estate is surrounded by vineyards and we have bicycles available for use as well as acres of fantastic land free of cars where you can ride.

There is also a beautiful swimming pool with a fantastic view over the vineyards and so passing the day at the estate is very easy to do! 

In the later afternoon we will will head to Chiusi for some shopping and exploration and check out the natural hot-springs there. 

Overnight at the Estate. 




Meals : Breakfast, Wine Tasting, Cooking Class

Day 3 : Under the Tuscan Sun: The Val D'Orcia

Where we visit :

Description :

This morning, after breakfast, we will depart to Montalcino, one of the highest towns in the Val D'Orcia.  From the estate it will take you approximately 30 minutes to arrive there.  Here, you can experience magnificent views over the Val D'Oria and visit one of the oldest churches in Tuscany.

From here, we will head to  to Casetllo Banfi, where we will have set up a wonderful wine tasting experience complete with some delectable Tuscan delicacies. 

In the afternoon, head to Pienza and Montepulciano to enjoy shopping, experience great cheeses and breathtaking vistas.

Dinner is on your own this evening, so choose any number of restaurants in Monteplciano that are outstanding in the area, or ask us for some great suggestions.

Overnight at the estate. 

Meals : Breakfast, Wine Tasting

Day 4 : Cortona, Arrezzo and Lago Trasimeno

Where we visit : Cortona, Arezzo

Description :

Today, you can head to the beautiful Etruscan towns of Cortona & Arezzo or drive around Lake Trasimeno, one of the largest lakes in South-Eastern Tuscany that borders Umbria.

Cortona is where under the Tuscany Sun, the movie was filmed and so it might be a good idea to watch this movie before arriving here! 

This evening, head back to the hotel for a beautiful dinner pool-side or in the gorgeous restaurant the estate has on site. 

Overnight at the Estate. 

Meals : Breakfast, Wine Tasting

Day 5 : Siena, San Gimignano and the Chianti Wineries

Where we visit : Chianti

Description :

Today we dedicate ourselves to the Chianti towns including Siena and San Gimignano.

In the afternoon,we will experience the Fattoria Montagliari, where you will enjoy a traditional Tuscan lunch and plenty of wine tastings overlooking the Vineyards and Greve in Chianti.

In the evening head back to the Estate for overnight.


Meals : Breakfast, Lunch, Wine Tasting

Day 6 : Perugia & the Choclate Arts - Assisi - Cooking Course

Where we visit :

Description :

Today, take a drive into Umbria to visit the beautiful hill-top town of Perugia which is famous ll over Italy and all over the world for the Perugino Chocolate that is produced here. You can stroll the streets here, and sample chocolate in a variety of stores.

In the afternoon, take a drive to the town of Assisi, that the famous St. Francis called his home and the San Francesco church is well worth a visit here.  St. Francis was the patron Saint of Animals and of the poor and yet Assisi, offers a rich and rewarding experience for all that come here.

In the afternoon, return to the estate where you will enjoy a cooking class that will be prepared with a master chef and accompanied by wine.

Farewell dinner at the estate.


Meals : Breakfast, Cooking Class

Day 7 : Time to say Arrivaderci Tuscany!

Where we visit : Tuscany

Description :

This morning after breakfast at the hotel, we will begin our journey back to Rome, where we will conclude our tour at the Rome rail station. We can arrange also transportation for you back to any hotel in Rome, to the Rome airport or allow you to get to a train station in Tuscany where you can continue your journey. 

Meals : Breakfast

Tour Highlights and What's Included

  1. Car rental as indicated in the itinerary
  2. Cooking class
  3. Daily Buffet Breakfast
  4. Excellent Photo Opportunities
  5. Stay in Luxury Villa in Tuscany
  6. Tastings of local products
  7. Wine and Olive Oil Tastings
  8. Wine Estate Visit

What's Not Included

  1. Gratuities of any type
  2. Meals not mentioned in the program
  3. Personal Expenses or Extras at hotels



Tuscany is among the most beautiful regions of Italy. The gentle curves and slopes of the land will enchant you. Tuscany is as famous for its wine and cuisine as it is for its landscapes. Wine production focuses on red wines like Chianti, San Giovese, Rosso di Montalcino, Rosso di Montepulciano, Bolgheri, and others.

Food is prepared with seasonal ingredients and enjoyed quietly by charming views. There are many medieval towns and castles, and in each of them you can find a treasure or two; it can be a painting by a famous artist hidden in an unusual church, a meal prepared by a passionate cook, or a great conversation with a local - whatever it is, for sure will be genuine.

Journeying through the hills and valleys, discovering the beauty of the land and the calm within yourself has attracted seekers of life and love to beautiful Tuscany for many years. The tradition continues to this day, and Tuscany welcomes them with her open arms. Major attractions: small and bigger medieval towns including Siena, San Gimignano, Monteriggioni, Volterra, Certaldo, Greve in Chianti, Montalcino, Montepulciano, Cortona, Pienza, and many others. Major festivals and events: Siena's Palio horse race, Puccini's Summer Opera Festival in Torre del Lago, Arezzo's Saracen Joust, Estate Fiesolana Music Festival, Cortona music and food festival, other local festivals.)



Montalcino is a town which is situated in one of the most enchanting natural landscapes of the world.   The long lines of vines have assigned Montalcino a prestigious position amongst Italian wine producers. The fabulous Brunello and Rosso di Montalcino are exported throughout the world and considered to be amongst the very best Italian wines.

Montalcino represents a wealth of history with its unchanged Medieval appearance: the Castle of Artigiano, the Castle Poggio alle Mura, the Romitorio Fortress and the Church of St Resituita, not to mention the Nearby Abbey of St Antimo. Culture and art are present in the United Museums which combine the Civic Museum and Diocesan Museumwhere one finds a host of frescos from the Siennese school of the XII and XIV centuries.

Visitors can also experience the popular festivals which represent historical traditions, such as the tournament for the opening of the hunting season, or the Festival of the Thrush, a spectacular event with processions, period costume and local gastronomy.



Encircled by walls and fortifications  designed and built starting 1511 AD by Antonio da Sangallo on the orders of the great Florentine, Cosmo I, Montepulciano cascades down a limestone ridge whose highest point is over 600 meters (1950 feet) above sea level.
The long and winding main street of Montepulciano extends from the Porta al Prato for 11.5 km to the Piazza Grande, and will take the traveler through the old medieval districts of  one of the most pleasant and satisfying of all Tuscan cities.
The Piazza, fronted by most of the city's most notable buildings, including the  Palazzo Comunale and the Duomo, perches at the utmost top of the hill, where Poliziani (the name the citizens give to themselves) mingle with visitors from nearby and far away.
The Duomo, with its plain, almost unfinished facade, was designed and built by Ippolito Scalza in 1630.  The most important work of art in the interior is a triptych done in 1401 by Bartolo, the "Assumption of the Virgin".
The Palazzo Comunale, a seemingly smaller version of Palazzo Vecchio, was built originally in the Gothic style, but the tower and facade were added in the 15th Century by Michelozzo.  Visitors are welcome to climb the tower where breathtaking views over the city and across the Tuscan countryside can be absorbed.  Next to the town hall is the Palazzo Tarugi, built in the 16th century.
Close by is the Chiesa Sant'Agostino, built in 1427 with a mix of Gothic and Renaissance elements by the architect, Michelozzo.  Note the elaborately carved portal.  The Palazzo Bucelli (1648), also close by,  has a lower facade into which are integrated Etruscan bas relief and funerary urns.
The Church of Jesus was built with a quasi circular plan by the Jesuit architect, Fra Andrea Pozzo.  Pozzo also worked on various other buildings in Montepulciano including the Palazzo Contucci (see above).
Sangallo the Elder also built the Temple of Madonna di San Biaglio, flanked by two campanile (bell towers) outside the city gates. It is also a Renaissance building built with butter- colored Travertine marble.  Sangallo started it in 1518, and remained pre-occupied with it until his death in 1534 and it is rightly recognized as his masterpiece. The design influence or inspired the architects of many of the palazzi in Montepulciano such as Palazzi Avignose, Cocconi, Cervini, Ganoni-Grugni, Contucci and Tarug (see above).
Also outside the walls and worth a peek are Chiesa Santa Chiara and Chiera Santa Maria, both done in the Baroque style.
Montepulciano is, of course, famous for its wines, particularly the Vino Nobile, a mellow red wine that evokes the scent of flowers and is shot through with a kind of iridescent orange color.  There are many less agreeable things to do than sit in one of the city's many cafes or restaurants to imbibe a glass (or two!) or purchase a bottle (or two!) at a local shop, which you can consume later during a lazy  Tuscan picnic.
Montepulciano is also the scene of a few enlivening annual festivals.  Arrive in late July-early August for the Cantiere Internazionale d'Arte arts festival founded by the German composer Hans Werner Henze.   Re-enactments of Montepulciano's turbulent history take place at the Brucello festival in mid August, and there is a parade, barrel race and banquet at the end of August, the Bravio dell Botti.
By Jesse Andrews, 2005 



The town of Pienza sits in the Val d'Orcia in Tuscany between the towns of Montepulciano and Montalcino.  Such are the characteristics and qualities of these Italian places that in 1996 UNESCO declared the town a World Heritage Site, and in 2004, the entire valley landed on the list of UNESCO's World Cultural Landscapes.
The Val d'Orcia, through which flows the River Orcia, is the quintessential Tuscan landscape.  Once dry and barren it has been transformed over the centuries into one of the most productive and beautiful regions in the world, dotted with small villages, parish churches, villas and castles, separated by a patchwork of vineyards, orchards, pastures and fields.  Roads and fields are lined with imposing oak, beneficent umbrella pine, tall and priestly cyprus, and varieties of other trees, shrubs and bushes that flare into color almost throughout the year.  Much of the valley is part of a large park system known as the Artistic Natural and Cultural Park of Val d'Orcia, consisting of five distinct areas (Pienza, Castiglione d'Orcia, Montalcino, Radicofani and San Quirico d'Orcia).
Pienza was built on a village called Corsignano that had been settled since known as Corsignano, which happened to be the birthplace (1405) of Aeneas Silvius Piccolomini, a Renaissance Humanist born into an exiled Sienese family, who later became Pope Pius II.  As Pope, he had the entire village rebuilt as an ideal Renaissance town - which has led historians to dub Pienza the "utopian" town.  It represents the first application of so-called humanist urban planning concepts, creating an impetus for planning that was adopted in other Italian towns and cities and eventually spread to other European centers.
Winding Roads throught the Val D'Orcia towards Pienza, Italy
The rebuilding work was done by Florentine architect Bernardo Gambarelli (known as Rossellino) under the guidance of Leon Battista Alberti  starting in about 1459 (the year that Columbus "discovered" American). Pope Pius II consecrated the Duomo, which sits across from the Piazza Comunale on Pienza's main piazza, the Piazza Pio, on August 29, 1462.  The Palazzo Piccolomini, the Pope's family home, and the Palazzo Borgia also front the piazza.  The travertine well on the Piazza carries the Piccolomini family crest. 
Though most of the buildings are decidedly Renaissant, the bell tower of the Duomo has a Germanic flavor as a result of Pope Pius' exposure to German architecture before he ascended to the Papacy. There is a brick bell tower on the Piazza Comunale, but it is shorter than its religious counterpart, and as such, the arrangement symbolizes the superior power of the church.
The Palazzo Borgia is now home to the Diocesan Museum, and the Duomo incorporates the Museo della Catedrale.  The Diocesan collection includes local textile work as well as religious artifacts.  Paintings include a 7th century painting of Christ on the Cross (La Croce), 14th century works by Pietro Lorenzetti (Madonna col Bambino) and Bartolo di Fredi (Madonna della Misericordia).  There are also important works from the 14th and 15th centuries, including a Madonna attributed to Luca Signorelli.
Streets in Town Centre of Pienza, Italy - Photo by Jesse Andrews
Not much remains of old Corsignano, but the Chiesa di San Francesco, with a gabled facade and gothic portal, is among the buildings that survived.  It is built on a pre-existing church that dated from the 8th century. The interior contains frescoes depicting the life of Saint Francis, those on the walls having been painted by Cristofano di Bindoccio and Meo di Pero, 14th century artists of the Sienna school.
Other buildings worth noting in Pienza include the Ammannati, the Gonzaga and the Palazzo di Cardinale Atrebatense, all built in the 15th century.
As small a town as Pienza is, it offers a complete Renaissance experience on a small scale.  The drive to and from Pienza, through the Val d'Orcia, and a few hours in Pienza itself, including a couple of hours eating delicious Tuscan cuisine at one of the town's  restaurant's is a fine idea.  Don't think about it too long though.  Just do it!
Please contact us today by either phone or email for assistance with this booking.
Email : team@italygroupspecialists.com
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Price Per Person : EUR 1,642.00

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