Relaxed Tuscany

Cathedral in Pienza Square
Cathedral in Pienza Square
The small charming town of Cortona
The small charming town of Cortona
Fresco at the Palazzo Comunale
Fresco at the Palazzo Comunale
Duomo in Florence
Duomo in Florence
Ancient fountain
Ancient fountain

A wealth of archaeological sites are hidden amongst the rolling hills and golden landscapes of Tuscany. The region has seduced countless civilisations for centuries. It all began with the Etruscans, but the Romans, medieval Christians, British aristocrats, and plundering Napoleon all share a space in the region’s fascinating history.

Our visually stimulating tour is set in the rolling Tuscan countryside - a gorgeous land of villas and vineyards. Based in a single hotel in the centre of Montepulciano, we enjoy a combination of expert-led archaeological visits and free time to explore. Highlights of the tour include visits to the hilltowns of Arezzo and Cortona, and the imposing Medici stronghold of Poggibonsi.

  • Discover the Palazzo communal in Siena and its breathtaking bell tower
  • Explore Cortona, the art and architecture city with a ‘diadem of towers’
  • Journey through the rolling countryside of Tuscany, punctuated with villas and avenues of cypress trees with free time to explore at your leisure


  • Romans
  • Medieval
  • Historic Churches
  • Ancient Greek


  • Special Access
  • Small Group
  • All Inclusive

Itinerary 2017

Day 1

We arrive in Italy and drive to our hotel in Montepulciano.

Day 2

This morning we explore Siena, the last town to hold out against the rise of the Medici. The Republic invested heavily in its wondrous Duomo, which we visit on our exploration of the city. We take plenty of time to explore and savour the marvellous Palazzo Comunale, and perhaps ascend its bell tower for the exceptional view over the town’s rooftops. We enjoy some free time this afternoon to spend at our leisure.

Day 3

We travel to Arezzo, another proud city state. It was described by Livy as one of the Capitae Etruriae, or Etruscan capitals, and is believed to have been part of the so-called Dodecapolis, a list of the twelve most important Etruscan cities. We explore the life and work of Giorgio Vasari, court architect to Cosimo I and biographer of the great artists. We then move on to the duomo, thought to be located on the site of the ancient city’s acropolis. There is the option to enjoy some free time this morning — perfect for languishing in the town’s central square, star of the Roberto Benigni classic Life Is Beautiful — or to visit Arezzo’s Archaeological Museum alongside your guide lecturer.

We enjoy the culinary delights of Tuscany tonight at one of the region’s fabulous Michelin-starred restaurants.

Day 4

Today, we enjoy a full day in Cortona, a small charming town in Arezzo’s Chiana Valley. Seated on the skirts of the mountains, with narrow cobbled streets and terracotta roofs, this is almost the archetypal medieval Italian city. Here, we discover the Accademia Etrusca — the home of an 18th century esoteric society and its fine museum — and the Diocesan Museum, holding works by Fra Angelico including his 1430s Annunciation altarpiece.

We enjoy a special visit to the impressive Etruscan tumuli of Sodo Melone below Cortona, the burial place of the city’s ancient aristocrats.

Day 5

We drive to Pienza, a Unesco World Heritage Site built by Pope Pius II. It was intended as a model Renaissance city, as a Papal retreat from Rome, and to test out mannerist ideals of city planning. This afternoon, we enjoy a visit to a local Tuscan winery to sample the vintages — Tuscan wines are, justifiably, celebrated, with a wealth of native grapes and a rich history of viticulture — providing a refreshing and relaxing end to the day.

Day 6

We enjoy a final visit to the great Medici fortress at Poggibonsi, relied upon by the Florentine Empire of Cosimo Medici. We transfer to the airport for our return home.

Itinerary 2018

Day 1

Today we arrive in Italy and drive to our hotel, ready to begin our adventure tomorrow.

Day 2

This morning we explore Siena, the last town to hold out against the rise of the Medici. This historic area’s centre was listed as a UNESCO Heritage Site and we take plenty of time to savour the marvellous Palazzo Comunale, which is a palatial town hall that houses some impressive frescoes and was built with a clear Gothic influence. During our visit, there will be the opportunity to ascend its bell tower to soak in the panoramic views over the city’s rooftops. Next, we have the opportunity to visit the incomparable Duomo. There will be free time in the afternoon for you to explore its honey-stoned streets, many churches and vibrant galleries. The boutiques and delicious-smelling pastry shops are abundant.

Day 3

Our day begins with a journey to Arezzo, where we will begin by uncovering the life and work of Giorgio Vasari. He was the court architect to Cosimo I and biographer of the great artists, and is regarded more highly as an architect than as a painter by contemporary scholars. We then move on to the Duomo, thought to be located on the site of the ancient city’s acropolis. We also explore the Basilicata of San Francesco, a late Medieval church, renowned for housing frescoes by Piero della Francesca. Enjoy the remainder of the afternoon at leisure, enjoy a traditional Italian coffee in one of the local cafes or, alternatively, you could visit the Archaeological Museum alongside your expert guide lecturer. The museum is housed within a former monastery and has fantastic collections.

Day 4

In the morning, we take a scenic drive to the idyllic village of Pienza, which has been listed as a UNESCO World Heritage Site and was built by Pope Pius II. This village, perched on a hill and offering spectacular views, is famed for its amazing Pecorino cheese and other gourmet delights. Later, in the afternoon, we will indulge in a tour of a local Tuscan winery, where we can sample some of the delicious vintages produced in the area. Tuscan wines, boast a rich history of viticulture and are widely celebrated for their deep flavours. This stop is the perfect way to unwind after a busy day.

Day 5

Our entire day will be spent in Cortona, which is a small and charming town in Arezzo’s Chiana valley. Enclosed by a stone wall that dates back to the Etruscan and Roman times, this city offers a host of interesting sites to visit including local museums, shops that sell regional handicrafts and also religious buildings. This area also produces some incredible red wines. During our time here, we discover the Accademia Etrusca and its fine accompanying museum, which houses fantastic historic artefacts and ancient art. Later, we move on to the Diocesan Museum, which hosts some truly remarkable works of religious art.

Day 6

After a final breakfast with the group, we transfer to the airport where we say our goodbyes to the group and catch our flights home.

What's Included

  1. Expert Guide Lecturer
  2. Tour Manager
  3. Local Travel - Private a/c coach
  4. Meals - All meals included with wine at dinner
  5. Entries & Tips - Entry to all sites in programme; tips included
  6. Field Notes
  7. Hotels
  8. Flights

Hotel Info

5 nights at a luxury Hotel in Montepulciano. 

Useful Information

For full information about Passport validity and Visa requirements as well as Health and Vaccination information please click here.

Book now

2017 Tour Details

Mon 11th September - Sat 16th September

Call for Availability


ex. flights: £1,975

sgl supp: £285


Led By: Oren Margolis

2018 Tour Details

Mon 3rd September - Sat 8th September



ex. flights: £2,075

sgl supp: £325


Led By: Oren Margolis

Guide Lecturer

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