Tour Details

Small-Group Montepulciano and Pienza Day Trip from Siena

From: £108.63

Duration: 8 hours

Category: Sightseeing

Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay hills south of Siena and take in the idyllic UNESCO-listed landscapes of Tuscany's charming Val d’Orcia region. Explore the beautiful towns, enjoy lunch and taste Pecorino cheese on a local farm!

Numbers are limited to eight people on this small-group tour, ensuring you'll receive personalized attention from your guide.

Meet your friendly guide in central Siena and head out of town in a comfortable minivan on one of Tuscany's panoramic roads, passing through the characteristic clay hills known as the Crete Senesi. Arrive first in the beautiful town of Pienza, which was entirely planned out by Pope Pius II, the humanist pope, to be the ideal Renaissance town.

Pienza is rightly considered the gem of the Val d’Orcia region; the town and the entire Val d’Orcia are World Heritage Sites. You'll have time to spend at leisure here, so make the most of it by shopping or exploring the pretty alleyways of this small town at your leisure. As you leave Pienza, enjoy the fantastic views of Tuscany’s famous picture-perfect scenery.

Your next stop is a local dairy farm, where you’ll feast on a wholesome and refreshing lunch (included) of fresh ingredients mostly produced on the farm. You’ll also enjoy a tasting of Italy’s salty Pecorino cheese, hear about the cheese-making process, visit the farm’s animals and learn about the lifestyle of the area.

In the afternoon, travel to Montepulciano, one of Tuscany’s biggest hill towns, located on a steep hill overlooking the amazing landscape of the Tuscany-Umbria border. With your guide, take a short walk around town to see the Piazza Grande at the top of the hill. You’ll then have free time to visit the town’s many stores, palaces or churches. Head to a family winery to enjoy a tasting of Montepulciano’s renowned wine and tour of the wine cellars before your relaxing ride back to Siena.

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Culture Shock Rating

We have a wide range of tours designed to give you an insight into the destination you're travelling in and there is something for everybody. The culture shock ratings considers the destination visited, transport used, activities undertaken and that "Wow, I'm really not at home now!" factor. While generalisations are always tricky, a summary of our gradings is as follows…

20%

This is the least confronting of our tour range. Transport used on the trip is either private or a very comfortable public option, the activities included are usually iconic sites and locations that are not all too confronting.

40%

The tour can include a mix of private and public transport providing a level of comfort that is slightly below what you would experience at home. Sites visited are usually iconic sites, tours can also include market visits, visits to communities etc that provide the traveller with a fantastic insight into destination.

60%

Expect to rough it for parts of this tour, whether it's a packed public bus where you are forced to stand, a visit to a local market, a local community, you are sure to have an experience that is very different from what you're used to at home.

80%

The comforts of your home town and the environment you are used to are more of a rarity. Expect some challenging transport options, visits to local sites and areas that don't resemble anything at home.

100%

You're out there in the global community! You are likely to be exposed to the elements, travel in whatever means of transport is available and basically take it as it comes, whatever comes! It can be tough.

Physical Rating

Our physical rating gives you an idea of how much huffing and puffing you can expect on the tour. While generalisations are always tricky, a summary of our gradings is as follows…

20%

These tours have very limited physical activity. Usually climbing in and out of the transport provided, walking through sites, markets etc included in the itinerary.

40%

These tours have a bit of physical activity but nothing that should challenge you too much. This could be climbing on and off public transport through to a walk through the destination you're travelling in, they can include walking only tours or a combination of walking and transport.

60%

These tours involve a bit of physical activity from walking up and down hills in the destination you're travelling in or the surrounding areas. Climbing on and off local transport or riding a bike up to 30 kms along predominantly flat terrain or jumping in a kayak for a gentle paddle on flat water.

80%

These Tours will provide you with some solid physical activity. Whether its bike riding, walking, trekking, kayaking or riding on public transport you will need to have a good level of fitness to enjoy this tour.

100%

Be prepared for some serious physical activity. These tours are our most challenging and involve some serious walking, hiking or bike riding. Can involve step climbs by foot or pedal and some challenging public transport options in the destination you are travelling.

Luxury Rating

Some trips are like a stroll on the beach, while others have you trekking alpine passes. Some of you thrive on camping out on the savannah, while others may prefer a hot shower and a comfortable bed in a lodge. Follow the grading systems below to find the right trip for you.

To help you choose the trip that's right for you, we've broken all of our trips down into four service levels. Measuring the comfort level of the accommodation and transport. So whether you're travelling on a budget and want to save money by using public transport, or prefer upgraded accommodation and are happy to pay a little more, then we have a level for you.

25%

This is grassroots travel at its most interesting

50%

Authentic experiences with some of the comforts of home

75%

For those who like to travel in comfort

100%

All the unique experiences wrapped up with a gold ribbon