Head in the clouds: 5 stunning hilltop towns in Tuscany

Posted by Katy Peck on 9 July 2019
Related property: Stigliano
Head in the clouds: 5 stunning hilltop towns in Tuscany

Stigliano is part of the Holiday Property Bond portfolio offering exclusive access to over 1,400 properties to its 42,000 investors across more than 30 locations. You can find out more about Stigliano here, but first some important information about the Holiday Property Bond. It is designed to provide holidays for life but it is an investment product so subject to charges, your capital is at risk and you may not be able to cash in during the first two years. For further details please read "How HPB Works"

Holidaymakers who have visited our property in the beautiful village of Stigliano will know just how enchanting Tuscany is. With endless blue skies, acres of vineyards and a breathtaking, rolling landscape, it’s no wonder people come back to this spectacular region again and again.

The Tuscan hills are dotted with plenty of charming towns and villages, from Stigliano itself to the many delights of Siena. However, these are just the start of the many hilltop gems to be found in this beloved part of Italy. We’ve picked five of our favourites, all an hour or less from our Tuscan property, to help get you started…

Monteriggioni – 30 minutes

Built between 1213 and 1219, Monteriggioni castle was originally constructed to be a lookout for any armies approaching Siena, while also controlling the cities of Val d’Elsa and Staggia. Over time, homes, shops and much more sprung up within its walls, creating a typical fortified village. Today it’s remarkably well-preserved. In fact, the village and its walls have remained more or less the same over the centuries, with narrow cobbled streets and ancient stone buildings.

The perfectly rounded shape of Monteriggioni looks almost artificial, although in reality it just follows the natural curve of the hill. Visitors can leave their cars in the car park at the bottom of the slope, then climb the short trail to enter the village through the France or Romea Gate. Due to its small size, it will only take a few minutes to reach the ancient centre of Monteriggioni, where you’ll find the Piazza di Roma, Church of Santa Maria Assunta and the rest of the castle. Make sure to take the time to stop into the Armoury Museum or take a short stroll around the village’s famous walls.

Colle di Val d’Elsa – 35 minutes

This delightful town, also known as the Hill of Elsa Valley, is well-known for its narrow, winding lanes and the creation of crystal glassware. It also has great views over Tuscany, some fantastic restaurants and a really unique, historical feel throughout… perfect for a relaxing day out.

The town is split into two parts – the old town at the top of the hill and the newer areas below. There’s plenty of parking throughout, including a very convenient car park at the historical centre. The older part of town is where you will find most of the attractions, including the Archaeological Museum, the Duomo and several traditional restaurants.  On the first Sunday of every month visitors can also enjoy an open-air glass blowing and engraving demonstration close to the Duomo. If that catches your imagination, the Crystal Museum in the lower town is a great place to learn more about how the town produces its delicate decorative pieces.

Montalcino – 55 minutes

One of many unmissable locations for wine enthusiasts is Montalcino, where the famous Brunello di Montalcino is produced. The beautiful spot is surrounded by vineyards producing this famous tipple, which is one of the most sought-after red wines in Italy. As for the village itself; the medieval settlement is surrounded by 13th Century walls, giving it a contained, magical feel amongst the expanse of the Tuscan hills.

Montalcino is the kind of place where the real pleasure comes from simply strolling along the main street, enjoying the atmosphere and perhaps stopping for a glass of wine or a coffee in the sunshine. There are many historic sites for you to discover within the town, including the fortress (built in 1361), the Chiesa Di Sant’Agostino and the Piazza del Popolo – the main square with its impressive clock tower. For history and art lovers, there are also some museums to look around, including Museo Civico and Diocesano di Arte Sacra.

San Gimignano – 1 hour

Known as the ‘Town of the Fine Towers’, San Gimignano is famous for its medieval architecture... it really is like taking a step into the past. The town became a UNESCO World Heritage Site in 1990 and is best known for the impressive and well-maintained towers which stretch high above the rooftops. Today only 13 of the original 65 towers remain standing, but they still manage to make the view approaching San Gimignano somewhat iconic.

Once you're inside the city walls, it’s time to turn your gaze downward. Visit the stunning Collegiate Church of San Gimignano, with its many frescos, as well as the Palazzo Comunale for a look at some medieval artwork. If you’re willing to work for your views, why not climb the 218 steps to the top of the Torre Grossa, the highest tower in town? Last but not least, find a place to sit down and enjoy a refreshing glass of Vernaccia di San Gimignano. This white wine is produced exclusively in San Gimignano and is one of the top wines in Tuscany.

Montepulciano – 1 hour

Balanced precariously atop a limestone ridge, Montepulciano is a classically beautiful Tuscan town. The town is most famous for its food and drink, with several beautiful vineyards producing Italy’s classic red wine, Vino Nobile.

Montepulciano is also known for its beauty – it was chosen as one of the filming locations for the Twilight ‘New Moon’ film. This brush with fame has increased the town’s popularity, although compared to the larger cities it remains very peaceful, even in peak season. The panoramic views can be enjoyed throughout the town and offer some unmatched glimpses of the surrounding countryside.

Montepulciano’s most spectacular place to visit is the Piazza Grande, which contains the town hall and unfinished cathedral. However, the whole town is extremely easy to walk around, with plenty of little shops and restaurants to duck inside. There are also a couple of beautiful churches which are worth popping into; see a masterpiece from the Sienese school in the Cathedral of Santa Maria Assunta or an elaborate altarpiece in the church of Santa Lucia.

With so many charming spots within easy reach of Stigliano, you certainly won’t run out of things to do. However, when you’re done exploring, or if you just want a day to relax and recharge, then a comfortable holiday property is a must. Our Stigliano property has a wonderful collection of holiday studios, apartments and cottages, all set within expertly converted historic buildings. With an outdoor pool, badminton, barbecues and much more, you’ll have everything you need during your Tuscan break.

Find out more how you can enjoy a stay at Stigliano property.

Katy Peck

Katy Peck

How can I find out more?

The Holiday Property Bond could do as much for your quality of life as it has done for many thousands of families who have already invested. That's why we invite you to get in touch with us in any of these 3 ways and please don't forget our unique 'Money back promise' and 'interest free loan' options.


We're so confident you'll be delighted with HPB
that we offer you a 'Money Back Promise'!

In regular surveys, Bondholders tell us how happy they are with HPB holidays. That's why we feel confident in giving you the extra reassurance of our unprecedented 'Money Back Promise':

If you take your first HPB holiday within three years of investing and are not, for any reason, entirely happy, you can apply to cash in your HPB investment within 14 days of your return. Whatever the encashment value, the parent company of the issuer of HPB will make up any difference so that you get back the full amount of your original payment, including charges.

This offer applies to a holiday at any HPB owned property which is taken by at least one of the Bondholders themselves.

Full details of the offer will be provided before you invest.

Request our brochure Speak to a representative Explore one of our UK sites

Please request our fully illustrated holiday property brochure

Please read "How HPB works" and then we will be delighted to send you our brochure, including our property portfolio, and your FREE copy of the May BOND Magazine. See the beautiful holiday homes and magnificent locations where you can spend your holidays as a Bondholder and learn how impressed Bondholders have been by our handling of the problems caused by coronavirus.

Please complete and submit the form or, alternatively, telephone our FREE brochure request line on 0800 230 0391

Request a brochure
Title *  
First Name *  
Surname *  
Email address  
Postcode *  
Telephone number
How did you hear about us?

We will use the details you provide above to send you our detailed HPB brochure and keep you updated about HPB holiday offers.

* Indicates required fields
HPB’s holiday booking service has been rated 4.7 out of 5 based on 3810 customer reviews on Feefo.

You can speak to one of our representatives

Your local HPB representative will be happy to call or video call you at a convenient time for an informal chat. Simply fill in your details and we'll do the rest.

Most of our representatives are Bondholders themselves and all have visited a number of Bond sites.

The representative will give you all the information you need and then leave you to make up your own mind. He or she will talk to you about your holiday requirements and what level of investment is needed to secure the kind of holidays you want.

Video chat now available with a local representative
Title *  
First Name *  
Surname *  
Email address  
Telephone number *  
Post code
iBy giving us your post code we can find a representative near you.
How should we contact you? *  
How did you hear about us?
Your message

One of our representatives will contact you using the information above.

* Indicates required fields

See our stunning holiday properties for yourself

Attending a Private Tour at an HPB holiday location is an enjoyable way to see what HPB has to offer.

You will be free to look around the site, view the properties and see the high standards of furnishings and facilities you could enjoy with HPB. A representative will be on hand should you have any questions.


This advertisement is issued by HPB Management Limited ("HPBM") registered at HPB House, Newmarket, Suffolk, CB8 8EH. HPBM is authorised and regulated by the Financial Conduct Authority and is the main UK agent and the property manager for HPB, issued by HPB Assurance Limited ("HPBA") registered in the Isle of Man and authorised by the Financial Services Authority there. The Trustee of HPB is HSBC Trustee (C.I.) Limited registered at HSBC House, Esplanade, St Helier, Jersey, JE1 1GT. The Securities Manager is Stanhope Capital LLP of 35 Portman Square, London, W1H 6LR.

Holders of policies issued by HPBA will not be protected by the Financial Services Compensation Scheme if the company becomes unable to meet its liabilities to them but Isle of Man compensation arrangements apply to new policies. No medical examination required. HPB is available exclusively through HPBM who will only charge for their services if you invest. HPBM promotes only HPB and is not independent of HPBA.