Hill Towns of Tuscany Highlights6 Days & 5 Nights 4.8 Read 17 reviews
- Southern Tuscany’s Val d’Orcia; Montepulciano, Pienza, Montalcino.
- Walks between Renaissance and medieval towns, vineyards and olive groves.
- The thermal baths at Bagno Vignoni.
- Sant’ Antimo Abbey; serenity and the sound of monastic chants.
- Great Italian food and wine; Brunello di Montalcino, Nobile di Montepulciano.
What To Expect
Self Guided | Go at your own pace on an independent holiday.
Inn to Inn Walking | A classic point to point walking trip, staying in a different location each night
This trip is suitable for:
Multi-Generational, Groups > 10
Ideal if you have an interest in:
- Historical Journeys
- Special Occasions
Grade & Terrain
This trip is graded ‘easy to moderate’ overall, however it should be noted that the terrain is hilly and summer temperatures can be high. Most of the route follows dirt tracks and trails, and you will be following minor roads only occasionally. On days 4 & 5 the walking is graded more towards the ‘moderate’ side as these are more challenging days.
The routes are waymarked in some areas, but not in others. However we provide you with detailed turn-by-turn route notes and maps and you will also have access to the Macs Adventure Smartphone App enabling you to follow the route using your phone's GPS so you will have no problems finding the way.
Stay in lovely 3 star hotels and country inns (agriturismo). We carefully select small and friendly accommodation that offers great value, food and welcomes, so you enjoy every minute of your stay. Many of our walkers choose to add extra nights along the walk to sample more of the wonderful walking and attractions available in Tuscany. If you choose to extend your holiday we would recommend spending extra nights in Pienza, Montalcino or Siena.
We will always try and accommodate you at the locations detailed below, but because of limited availability we may have to accommodate you at an alternative location of the same or better standard.
This independent walking holiday is available to solo walkers and a supplement is payable, as some of the costs are not shared. If you require single rooms in your party we will of course try to accommodate your request, subject to availability and payment of a single supplement.
The delicious Tuscan food and wine available locally is undoubtedly a highlight of this holiday. The price of your holiday includes a hearty breakfast each morning. Lunch and dinner are not included so you are free to choose from the available options. Most of your accommodations will more than happy to provide a packed lunch on request and this can be booked on arrival. Alternatively your route includes details of local shops and convenient lunch stops on the way. Dinner is available either at your accommodation or nearby restaurants.
- Overnights in small hotels and country inns (3-star standard).
- Breakfasts included.
- Daily baggage transfers between hotels.
- Taxi transfers as per itinerary
- Information Pack, maps, route notes, GPX tracks, access to our smartphone app.
- Emergency telephone support from our local partner and UK office.
- Travel insurance (required).
- Travel to starting point/from finish
- Lunches, dinners, drinks and snacks.
- Taxi transfers or public transport should you need to skip a stage.
- Personal equipment
- Extra nights before, during or after your walk
- Private airport transfers.
When To Go
This tour is available from March to November. Although you can walk in July and August if you want it is not recommended as it can get very hot.
Getting to the Start
By Air: We recommend flying to Pisa, Florence or Rome, and then you can catch the train from the city centre railway station to Montepulciano (usually changing in Chiusi or elsewhere). Approx. journey times to Montepulciano; Pisa 2h50-3h20, Florence 1h50-2h15, Rome 1h50-3h15). Train timetables are available at Trenitalia; www.trenitalia.com
If you wish, from Chiusi you can opt to take a local bus, or taxi the short distance to Montepulciano (25 mins, payable locally).
Getting from the End
At the end of your trip, we transfer you to Buonconvento train station, where you can catch the train to Siena. From Siena you can take the train back to Pisa (2h00-3h15), Florence (2h15-3h15) or Rome (2h15-3h20). Again, please see Trenitalia’s website for timetable planning.
Baggage TransferYour bags will be collected from your accommodation each day and moved onto your overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.
The distances and ascent/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.
Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes and a day pack.
It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.
This walking trip is graded moderate and involves 3 - 7 hours of walking each day so you should enjoy an active lifestyle to get the most from your time in Tuscany. If you are unable to walk on any day you can use taxis or public transport to move onto the next nights accommodation.
Spring in Tuscany is sublime and April, May and June are absolutely lovely. Autumn is probably our favourite time of year as the landscape is made up of a gold and red pallet so September and October are unmissable. July and August can be very hot so you will have to start walking early to miss the heat of the day, although the towns and villages are buzzing, which is great.
We suggest you book as soon as your plans are finalised Tuscany is extremely popular especially during July/August.
Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.
You will need good walking shoes/boots, comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc.
Either Pisa, Florence or Rome are convenient and you can reach the start/end of the walk by train in an hour or two.
You can use public transport or local taxis to continue to your next overnight stop.
ItineraryDay 1 Arrive Montepulciano
Your Tuscan walking tour begins in the medieval and Renaissance hill town of Montepulciano.
Montepulciano is easily accessible via Rome, Florence or Pisa; catch the train to Chiusi then take a local bus or short taxi ride to Montepulciano. Admire the impressive views over the rolling Tuscan landscape that you’ll be exploring over the next week.
Owner Cinzia Caroli offers a warm welcome to all guests coming to her extraordinary charming B&B. Rooms are museum-like, decorated with period Italian antiques and frescoed ceilings while on the other hand you will have just recently renovated bathrooms with modern fittings.
The Hotel Il Marzocco has been operating as a hotel since 1860 and operated by the same family since 1900. It has the welcoming and refined atmosphere of a large country house and is furnished with genuine XIX century furniture.
Starting from the San Biagio church you follow a quiet track to the peaceful village of Montichiello where you can pause for a relaxed lunch or perhaps just a quick cappuccino before continuing on to Pienza.
Pienza is a UNESCO World Heritage site with unique Renaissance architecture. The town is well known for its delicious pecorino cheese and truffles; this is a great spot to indulge in Tuscan treats! Your tranquil hotel has an outdoor pool, and is just steps from the ancient walled town.
Recently renovated the Hotel Corsignano is a newly certified a “Green” Hotel. This beautiful 4- star Hotel is beautifully furnished and extremely comfortable, set in the frame of Tuscany's most beautiful and unspoilt area, reaching from Pienza to the Orcia-Valley.
Hotel Residence San Gregorio is situated a few hundred meters away from the ancient walled town of Pienza, in the heart of Tuscany. It offers an ideal exclusive environment to spend a night or a few days immersed in the magical atmosphere of a renaissance town, considered to be an architectural jewel.
Today you wander through a beautiful region of rolling hills, oak woods, cypress trees and pretty villages. The thermal baths complex at Bagno Vignoni is the perfect location to spend the afternoon soaking up the Tuscan warmth.
Surrounded by the warm steam from the thermal spring, continuing the legend of healthy water, one finds the ancient construction of the Rossellino, home of Pope Pius II Piccolomini, today known as the Hotel "Le Terme". The rooms are decorated in classical style and the restaurant specialises in traditional Tuscan style food where simple ingredients are combined into delicious dishes. All complimented by delicious wines from the surrounding villages.
A more challenging but rewarding day’s walking awaits as you follow dry riverbeds through a fairly wild environment to Sant’ Antimo, an isolated abbey situated in a pastoral landscape. After exploring the abbey transfer to the medieval town of Montalcino.
Located in the medieval old town of Montalcino with magnificent views of the Tuscan Hills. With an emphasis on excellent service this charming small hotel is situated in part of the eighteenth-century “Catasto Leopoldino” in the historic centre of Montalcino. However, there is reason to believe that the building may have been used since the Middle Ages (owing to its location in the vicinity of Porta Burelli) as a shelter for the Sienese people fleeing from the Florentine army.
A charming retreat in the heart of Montalcino, a family-run Hotel in a warm and quiet building, facing a gorgeous landscape over the Tuscan countryside. This is “Il Giglio”. The hotel has just 12 rooms, each one with cast-iron bed frames, painted ceiling and travertine stone bathrooms in a harmonious blend of rustic Tuscan style and classical elegance. The breathtaking panorama through the windows contributes to create an atmosphere that can only be experienced, never described.
A hearty breakfast will set you up for a long but enjoyable day of walking in the famous Brunello wine region, passing vineyards and olive groves, then again entering the beautiful Tuscan landscape of the “Crete Senesi” and Buonconvento, where you will stay in a lovely agriturismo (country hotel) with an outdoor pool; the restaurant serves food grown on the estate.
Fattoria Pieve a Salti is an agriturismo that has been converted from restored farm ruins into a stunning country hotel complex including a swimming pool and health centre. The rooms are furnished in traditional rustic Tuscan farm style.
Hotel Ghibellino is a modern 23 room three-star hotel in the centre of Buonconvento. It has an excellent reputation and the comfortable air-conditioned rooms are a relaxing haven.
Take a transfer to Buonconvento train station, where you can catch the train to Siena and then continue your journey on to your chosen airport. Alternatively, perhaps continue your travels further within Italy; Tuscany combines perfectly with our coastal walks of the Cinque Terre or Amalfi Coast.
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