Tuscany Discovery Tour

Discover the Tuscan countryside and hilltop villages


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Activity types:

  • Central location
  • Culture
  • Flora
  • History

Holiday overview

The ancient medieval town of San Quirico d'Orcha lies in the heart of the Orcia valley, amidst a wonderful landscape of green and golden hills for which Tuscany is famous. Due to its position in the middle of the main Via Francigena pilgrimage route, it has long been a staging post for wayfarers, pilgrims and merchants on the way to Rome. San Quirico is just one of the many hilltop towns and villages that dominate the skyline of this part of Tuscany.

During our stay we'll visit a number of these including beautiful Pienza, Motalcino, and Montepulciano. These fortified villages contain a wealth of architectural treasures and offer an insight into the turbulent history of the Republic of Siena and the legacy of Etruscan and Roman settlement.

Holiday Highlights:

  • The beautiful Renaissance city of Siena, famous for the Palio, makes a fascinating day 
  • Enjoy a day in Umbria and a boat trip on Lake Trasimeno 
  • Explore San Gimignano, the ‘city of beautiful towers’

Price Includes Good:

  • Quality en-suite accommodation in one of our European partner hotels
  • Half Board – continental breakfast and evening meal
  • The services of an experienced HF Holidays’ leader
  • Full day excursions with all essential transport in resort
  • ‘With flight’ holidays include return flights from the UK and hotel transfers



In pictures...


Hotel Albergo Palazzuolo in San Quirico d'Orcia, Tuscany, Italy

The 3-star Hotel Albergo Palazzuolo is set in a peaceful location in the countryside surrounding the village of San Quirico, and is very convenient for the local amenities. This family owned hotel was originally an attractive farmhouse, extended on both sides to incorporate the bedrooms. This hotel has excellent views to the gentle hills of Montalcino. The hotel offers good standards of service and comfort and has a relaxing atmosphere after your day’s walking.

Your room

The hotel has 42 comfortable bedrooms, all en-suite with shower. 

All bedrooms also have:
  • TV
  • Telephone
  • Air conditioning
  • Fridge
  • Hairdryer
Hotel Albergo Palazzuolo bedroom


Hotel Albergo Palazzuolo lounge Hotel Albergo Palazzuolo facilities consists of:
  • Lounge
  • Bar
  • Terrace
  • Attractive gardens
  • Outdoor swimming pool (swimming hat is required)


Our holidays at Hotel Albergo Palazzuolo are on a Half Board basis and include breakfast and evening meal.

The self-select continental breakfast includes cereal, cheese and cooked meats, bread, croissants and home-produced honey. Tea and coffee is available.

Evening meal
The five course set menu features many Tuscan specialities, using homemade pasta and locally-produced oil, meat and cheese. An alternative is available for vegetarians; however we recommend that those with special diets discuss their requirements with the manager or chef.
There is a well-stocked bar serving beer, wine and spirits.

Lunch (payable locally)
You can buy a picnic lunch from the hotel (order the night before). Alternatively ingredients can be bought in local shops, including a supermarket five minutes' walk away. On some days it may be possible to eat in a café during a walk or excursion; your leaders will advise you of all the options.
Hotel Albergo Palazzuolo outside dining

Your evenings

The friendly atmosphere of our holidays continues into the evening.

Enjoy a glass of wine or local beer before hearing about the next day's activities, then join your fellow guests for a leisurely meal.

One evening our guests can learn more about olive oil and take part in a tasting session, very popular with our guests.

Your leader will be checking out for other local events going on nearby, or you may prefer to relax on the terrace enjoying the panoramic view or in the bar with a drink.


During your Discovery Tour you'll have the opportunity to visit many fascinating places. The following is our provisional programme, and your HF Holidays' leader may adjust it at their discretion, taking into account factors such as weather, local opening times, or other events. This holiday includes active sightseeing and you should expect to spend lots of time on your feet.

For maximum flexibility, admissions are not included; Please allow up to €40 per person for entrances (there may be concessionary and group discounts which may reduce this price). Please bring cash as card machines are not always available at all venues.

Sometimes things happen beyond our control – the weather, traffic jams or changes at the places we visit. If we need to adjust your holiday programme, for whatever reason, your leader will help smooth the way.

Day 1: Arrival Day

Day 2 : Pienza and Montepulciano

We'll visit two awesome hilltop towns, Pienza and Montepulciano. In Pienza which is Pope Pius II’s ideal Renaissance town,  you'll find charming cobbled streets and panoramic ramparts with an opportunity to buy some of the delicious locally produced pecorino (sheep’s cheese). We'll discover Montepulciano, one of the highest Tuscan hilltop towns, renowned for its "pici" pasta, lentils and honey. Connoisseurs consider its Vino Nobile among Italy's best.

Day : 3 Umbria and Lake Trasimeno

We will spend a full day in neighbouring Umbria, known as the ‘Green Heart of Italy’. We will pick out some of the highlights such as Castiglione del Lago and enjoy a boat ride on Lake Trasimeno to Isola Maggiore.

Day 4 : Siena

Our Local Guide will explain the history of this atmospheric city as you wind your way through the medieval alleyways of the city with the Piazza del Campo at its heart. This small city has a large character including the cathedral city museum and the Torro Del Mangia; you get a birds-eye view of the city from the top .

Day 5 : Montalcino and Sant’Antimo

This hilltop town west of San Quirico is famous for its wine production, but on this excursion we will take in the Fortezza with an optional walk along the ramparts. Lunch will be spent here before continuing to the very impressive Abbazia di Sant’Antimo, one of the most beautiful churches in Tuscany. We will return via the scenic Monte Amiata National Park.

Day 6: Free Day

On our 7 night holidays we allow one free day where there is no organised excursion. This is an ideal opportunity for you to relax, enjoy the hotel facilities or explore independently.

 Day 7:  San Gimignano

The ‘city of beautiful towers’ is one of the best preserved medieval towns in Tuscany. Join our leader for an exploration of this delightful place.

 Day 8 : Departure Day

In the Evenings

The friendly atmosphere of our Discovery Tour continues into the evening. We’ll enjoy a leisurely meal and then you may also like to listen to local musicians, relax with a book in a quiet lounge or enjoy a drink at the bar. On one evening during the week, we’ll take a coach trip to enjoy an evening stroll and a drink in San Quirico.


Local area

San Gimignano

San Gimignano is a medieval walled hill town between Siena and Pisa. It is famed for its fourteen surviving towers and surrounding walls. The historic centre of the town is also a UNESCO World Heritage Site. One notable attraction is the Duomo (Cathedral), which has a beautiful interior with 14th Century frescos, which have never needed restoring. The film “Tea with Mussolini” had several scenes filmed in the Duomo and in San Gimignano main square. The Rocca was built in the 14th Century to protect the town from attack; this fortress also boasts extensive views across the surrounding countryside. It is also worth visiting the Church of St. Augustine, which is a little more off the tourist trail, and has ornate frescoes to marvel at.


Situated only 4miles from San Quirico, Pienza is a historic town, famous for being the birth place of Pope Pius II, when it was called Corsignano. In 1996, the town was also credited with being a UNESCO World Heritage Site. One of the main architectural features of Pienza is the Palazzo Piccolomini built by Pope Pius II as his summer home in the Renaissance period. This was part of his project to build the ‘ideal city’. The Pieve di Corsignano is an ancient Church with Romanesque architecture on the western edge of Pienza. This contains the baptismal font where Pope Pius II was christened. The Diocesan Museum contains works of art from several churches. The museum was founded in the early 20th Century and contains an impressive collection.

Bagno Vignoni Hot Springs

Bagno Vignoni is a town with natural springs that have minerals with healing properties. As a result, this has become an area of pools and spa facilities. The renaissance pool in the town was built by the Medici family and has been popular since with famed nobles such as Catherine of Siena in the 14th Century. Many other wealthy people would visit the town to take ‘the cure’. The hot springs are still accessible today, and make a lovely day out.

Did you Know?

Val d’Orcia is a UNESCO World Heritage Site.


We recognise that everyone’s travel arrangements are unique, so all our holidays to Europe can be booked ‘with flight’ or ‘without flight’, giving you more flexibility and choice.


Travel by plane


‘With flight’ holidays – the hassle free option

Book your holiday ‘with flight’ and choose between Heathrow or Manchester flights to Pisa airport. For flight times and prices please see the Dates & Prices tab.

If you choose this option we automatically include return transfers between the airport and the hotel. The coach transfer takes approx 2 hours 30 minutes to the Hotel Albergo Palazzuolo.

Please note guests travelling to Bonassola will also fly in to Pisa. Leaders will be available at the airport to direct guests to the correct transfer coach.




Driving to us

‘Without flight’ holidays – the flexible travel option

Alternatively, tailor your journey to suit you by booking your holiday ‘without flight’ allowing you the freedom to book your own flights from your local airport.

If you choose this option, transfers are not included in the price. However, below are some suggestions to help you reach your destination:

  • We can book you a seat on the HF Holidays’ transfer coach from Pisa airport. This is timed to meet the HF Holidays’ flights* (provisional flight times can be found on the dates and prices tab or you can call us on 020 8732 1220 for more information). Cost per single journey is £49.50. Please note guests travelling to Bonassola will also fly in to Pisa. Leaders will be available at the airport to direct guests to the correct transfer coach. 
  • Why not let us book you a private taxi transfer - price on request.

Transfers must be pre-booked.  Please call 020 8732 1220 for more details

* Please note that HF Holidays is not responsible for your onward travel if you fail to meet the transfer coach


Alan Winfield - Discovery Tour Leader

Alan Winfield has been leading tours for HF Holidays since 1990. He leads Discovery Tours in the UK, and Walking holidays in the UK, Europe and Worldwide. He also leads City Breaks in Italy. A Yorkshireman by birth and upbringing, he now lives in Cambridge. Alan is a retired teacher and university lecturer and his other passion is amateur theatre where he has taken roles in musicals for over 50 years.

Alan was a brilliant guide and leader whose social skills and expertise made the holiday very enjoyable indeed.

Jim Hart

Jim is a professional horticulturist with more than 35 years' experience working in local authority parks departments and commercial nurseries, in Britain and abroad. For more than 15 years he was a lecturer in plant production and landscape management. He has also run his own nursery and landscape design business. Jim combines visiting gardens and plant spotting with hiking and sightseeing in various countries. Jim leads Walking, Discovery and Garden Tours in Europe.


Dates & Prices

We're sorry, there are no dates available for this holiday at the moment. Please check out our other tours and breaks or call our team on 0345 470 8558 to be notified of new dates as soon as they become available.

Prices are per person


  • Double room for sole occupancy: £19 per night
  • Non-member associate fee: £10 per person

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