Day 1: Arrive Montepulciano
Your Tuscan highlights 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 four days.
Day 2: Walk to Pienza
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.
Walk: 15 km
Day 3: Walk to Bagno Vignoni Thermal Baths
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.
Walk: 16 km
Overnight: Bagno Vignoni
Day 4: Walk to Sant’ Antimo, transfer to Montalcino
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.
Day 5: Walk through the 'Crete Senesi' to Buonconvento
A hearty breakfast will set you up for a long but enjoy 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.
Walk: 17 km
Day 6: Onward travel
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.
5 nights accommodation is included in your trip; 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 adding time in 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.
Many of our clients choose to add extra nights along the walk or at the start/end of the walk. These can be added at the time of booking.
B&B l'Agnolo - Montepulciano
Located in the heart of Montepulciano. This once grand home is now a beautiful small and comfortable Bed and Breakfast, still displaying the ornate high fresco ceilings and wonderful surroundings. Expect a warm welcome during your stay in this unique bed and breakfast.
Hotel Marzocco - Montepulciano
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.
Residence San Gregorio - Pienza
Residence San Gregorio is situated a few hundred meters away from the ancient walled town of Pienza, in the heart of Tuscany. The Hotel Residence San Gregorio is 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.
Hotel Le Terme - Bagno Vignoni
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.
Hotel Dei Capitani - Montalcino
Hotel Dei Capitani is fantastically positioned in the centre of the Medieval town of Montalcino. You will delight in the wonderful panormaic views over the Tuscan countryside, from the beautifully designed swimming pool and terrace area. You can expect a warm welcome during your stay in this charming Hotel.
Hotel Il Giglio - Montalcino
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.
Fattoria Pieve a Salti - Buonconvento
A traditional Tuscan agriturismo, offering total tranquility and overlooking the incredibly beautiful Tuscan countryside. Enjoy the vast array of facilities on offer, with outdoor swimming pool, spa, horseriding and the rustic restaurant which serves excellent home grown food from the estate.
You can start this walking tour anytime between March and October. Tuscany is very popular so it’s best to book as far in advance as you are able to. Please bear in mind that July and August can be very hot for walking.
Time of Year
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 ideally need to start an walks early to miss the heat of the day, although the towns and villages are buzzing, which is great.
Your 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.
Single Rooms & Solo Walkers
This trip is available to solo walkers and a supplement is payable as some of the costs are not shared. Should you wish to have single rooms in your party then again a single supplement is payable.
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.
The route is not always waymarked but we supply detailed maps, route notes and access to the Macs Adventure Smartphone App so you will have no problem following the route.
Experience & Fitness
This trip is graded ‘easy to moderate’ overall, however it should be noted that although some of the daily walks are relatively short, 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.
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.
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.
Getting to Montepulciano
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 Buonconvento
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.
- 5 Nights in small hotels and country inns (3-star standard).
- 5 Breakfasts.
- Daily baggage transfers between hotels.
- Taxi transfers as per itinerary (day 4 & 6).
- 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 Montepulciano and from Buonconvento train station.
- Lunches, dinners, drinks and snacks.
- Taxi transfers or public transport should you need to skip a stage.
- Personal equipment.
- Single room or solo walker supplement.
- Extra nights before, during or after your walk.
- Private airport transfers.
We are often asked the following questions and we hope that you will find the answers useful. Please do not hesitate to contact us if you have any other questions or for more advice from our team.
How do the baggage transfers work?
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.
How fit do I need to be?
This walking tour is graded easy to moderate and involves 3 - 7 hours of walking each day so you should enjoy an active lifestyle to get the most from your trip. If you are unable to walk on any day you can use taxis or public transport to move onto the next night's accommodation.
When is the best time of year?
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 your walks early to miss the heat of the day, although the towns and villages are buzzing, which is great.
How far in advance do I need to book?
We suggest you book as soon as your plans are finalised Tuscany is extremely popular especially during July/August.
What personal equipment do I need?
You will need good walking shoes/boots, comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc. Our comprehensive pre-departure information pack has a good kit list.
Which is the best airport?
Either Pisa, Florence or Rome are convenient and you can reach the start/end of the walk by train in an hour or two.