Exploring Tuscan Hilltop Towns
Exploring Tuscan Hilltop Towns
Exploring Tuscan Hilltop Towns
8 Days Starting in Montepulciano, Italy and ending in Siena, Italy
Visiting: Montepulciano, Pienza, Bagno Vignoni, Montalcino, Buonconvento, Monte Oliveto Maggiore, Siena
Tour operator:
Tour code:
JTM
Group Type:
Independent
Guide Type:
Self Guided
Tour operated in:
EnglishTrip Styles:
Interests:
Cultural, Foodie and Wine Tours, Gardens & Nature Tours, History
Tour Overview
Embark on an unforgettable journey through the heart of Tuscany with our "Exploring Tuscan Hilltop Towns" tour. This self-guided adventure begins in the medieval town of Montepulciano and takes you through a series of enchanting hilltop villages, including Pienza, Bagno Vignoni, and Montalcino. Along the way, you'll savor regional culinary specialties, from pecorino cheese to exquisite local wines, and marvel at the stunning landscapes of cypress-lined hills and vineyards. Enjoy comfortable stays in 3-4 star hotels and agriturismos, with daily breakfasts and luggage transfers included. Conclude your journey in the historic city of Siena, renowned for its magnificent architecture and vibrant culture.
Highlights
Itinerary
Day 1 : Arrive Montepulciano
Location: Montepulciano
Accommodation Name: Hotel
Make your own way to Montepulciano. Standing high atop a hill in southern Tuscany, Montepulciano is a medieval town full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners. It boasts vast panoramas all over the wonderful Val d'Orcia and Val di Chiana valleys that surround it.
Day 2 : Walk To Pienza - 13 Km / 8 Miles, 4 Hrs
Location: Pienza
Accommodation Name: Hotel
Meals Included: Breakfast
Starting from the San Biagio Church you follow a quiet track to the peaceful village of Montichiello where you can stop for a relaxed lunch or perhaps just a quick cappuccino before continuing 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; a great spot to indulge in Tuscan treats!
Day 3 : Walk To Bagno Vignoni - 12 Km / 7.5 Miles, 4 Hrs
Location: Bagno Vignoni
Accommodation Name: Hotel
Meals Included: Breakfast
Today you wander through rolling hills, oak woods, cypress trees and pretty villages. From the start of the walk you will have views across the valley. Descend before climbing up to the town of San Quirico d' Orcia, a walled city with a 12th century church. Make your way to the village of Bagno Vignoni with its thermal hot springs.
Day 4 : Transfer To Castelnuovo Dell'abate And Walk To Montalcino - 13 Km / 8 Miles, 5 Hrs
Location: Montalcino
Accommodation Name: Hotel
Meals Included: Breakfast
You will be transferred from Bagno Vignoni to Castelnuovo dell'Abate. As you arrive in the village, you will enjoy the stunning beauty of Sant'Antimo Abbey, a former Benedectine monastery dating back to the 8th century A.C. The first section of the walk to Montalcino will bring you to some panoramic views overlooking the beautiful Orcia Valley. Prepare for some exquisite local wines as you arrive in Montalcino.
Day 5 : Walk To Pieve A Salti 18 Km/11 Miles Or Buonconvento 15 Km/9 Miles - 5.5 Or 5 Hrs
Location: Buonconvento
Accommodation Name: Hotel
Meals Included: Breakfast
A hearty breakfast will set you up for an 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 Sensi and Buonconvento. Depending on accomodation booked, you will either spend two nights in Pieve a Salti or Buonconvento.
Day 6 : Transfer To Monte Oliveto Maggiore Monastery, Return 14 Km / 8.5 Mles, 5 Hrs
Location: Monte Oliveto Maggiore
Accommodation Name: Hotel
Meals Included: Breakfast
After breakfast transfer to the monastery at Monte Oliveto Maggiore. Begin your walk at the watchtower and make your way to the little village of Chiusure. Pass farmhouses along the way and once more this walk provides great views of the Crete Senesi landscapes.
Day 7 : Transfer To Monteroni D'arbia, Walk To Arbia, Train Siena - 10 Km / 6.2 Miles, 4 Hrs
Location: Siena
Accommodation Name: Hotel
Meals Included: Breakfast
Today you will start with a short transfer to Monteroni d’Arbia from where you start the walk towards Siena. Hike through a landscape of rolling hills and small hamlets as the unmistakable sight of Siena appears in the distance. Once you reach Arbia train station take the train into Siena. Option to pre-book a vehicle transfer. Enjoy the magnificent beauty of Siena, famous for its biannual “Palio” horse race, held in the most beautiful shell-shaped square in Europe: the Piazza del Campo. Don’t miss a visit to the Duomo, an architectural treasure, and numerous imposing medieval palaces.
Day 8 : Arrangements End After Breakfast
Location: Siena
Meals Included: Breakfast
After breakfast, make your way to the train station for your onward journey or book an extra night to spead more time exploring this wonderful city.
What's Included
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Accommodation
7 nights 3 or 4 star hotels and agriturismo -
7 breakfasts
Enjoy 7 breakfasts during your stay.
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7 nights in 3-4 star hotels & agriturismo
Stay for 7 nights in comfortable 3-4 star hotels and agriturismo.
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Vehicle transfers day 4, 6 & 7
Vehicle transfers are provided on days 4, 6, and 7.
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Luggage transfer
Luggage transfer is included (1 bag per person not weighing more than 20kg).
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Digital information pack
Receive a digital information pack with a navigational app (usable offline) that includes route notes and maps. A smartphone is essential.
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Emergency hotline
Access to an emergency hotline is provided.
What's Not Included
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Evening meals, all lunches & beverages
Evening meals, all lunches, and beverages are not included.
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Entrance fees
Entrance fees are not included.
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Travel insurance
Travel insurance is not included.
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Travel to the start and from the end point of the trip
Travel to the start and from the end point of the trip is not included.
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Personal expenses
Personal expenses such as laundry and phone calls are not included.
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Tourist taxes
Tourist taxes are not included.
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Solo traveler supplement
A supplement will apply if you are traveling solo or book a single room.
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Guide
This is a self-guided holiday; a guide is not included.
Grading
Introductory to Moderate. There are nonetheless some steep and quite long hills, some fairly steep but short descents and some paths with rough gravel, stony and occasionally muddy surfaces. Fitness: High standard of fitness is not necessary but clients should be able to walk for up to 7 hours a day in hot sun on dusty or stony tracks.
Mode of Transport
Vehicle transfers are provided on days 4, 6, and 7, along with luggage transfer for one bag per person. Additionally, a train ride from Arbia to Siena is included.
Accommodation
Enjoy 7 nights in comfortable 3-4 star hotels and charming agriturismo accommodations, providing a perfect blend of modern amenities and rustic Tuscan charm.
Check out our Q&As
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What type of accommodation is provided during the tour?
The tour includes 7 nights in 3-4 star hotels and agriturismo.
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Are meals included in the tour package?
Yes, the tour includes 7 breakfasts. Evening meals, all lunches, and beverages are also included.
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Is luggage transfer provided during the tour?
Yes, luggage transfer is provided with a limit of 1 bag per person not weighing more than 20kg.
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What kind of support is available during the tour?
A digital information pack with a navigational app, route notes, and maps is provided. There is also an emergency hotline available.
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Is this a guided tour?
No, this is a self-guided holiday.
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Are there any additional costs I should be aware of?
Yes, personal expenses such as laundry and phone calls, travel insurance, travel to the start and from the end point of the trip, and tourist taxes are not included. A supplement will apply if you are traveling solo or book a single room.
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What is the difficulty level of the tour?
The tour is graded as Introductory to Moderate. There are some steep and long hills, fairly steep but short descents, and paths with rough gravel, stony, and occasionally muddy surfaces.
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What fitness level is required for this tour?
A high standard of fitness is not necessary, but clients should be able to walk for up to 7 hours a day in hot sun on dusty or stony tracks.
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What are some of the highlights of the tour?
The tour highlights include visiting medieval villages and hilltop towns, enjoying regional culinary specialties, and experiencing the cypress-lined hills and vineyards of Tuscany.
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What happens on the last day of the tour?
On the last day, after breakfast, you can make your way to the train station for your onward journey or book an extra night to spend more time exploring Siena.
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Self-guided holidays - inclusions
We have designed our self guided walking and cycling tours to include a number of elements to help you enjoy your holiday more, while leaving out some things to give you more freedom to tailor the trip to your needs and interests. Refer to the Trip Notes for more information on the specific inclusions for each trip. What’s included: - Detailed Route Notes - Accommodation - Luggage transfers - Any scheduled transfers as per Trip Notes - Emergency support - Some meals (mostly breakfasts) What’s NOT included: - Transport to/from start/finish points - Most meals - Any entrance/park fees - Travel insurance - Personal expenses along the way - Unscheduled transfers required during the trip
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Trip Grading & Preparation
Match your level of fitness & requirements Please read this information carefully to find out which grade is most suited to your level of fitness and requirements. To make the most of your Walkers' Britain holiday it is essential and your responsibility to choose a trip that is well within your capabilities. All our active holidays are graded and clearly marked in each trip description. All mountains have uphill and downhill sections and by definition walking and cycling demand some effort. However all things are relative, and these grades assume that you are a reasonably active person who enjoys walking or cycling. Few trips are extreme and most allow ample time for sightseeing and enjoying the scenery. If in doubt about the grade of any holiday, please contact us for advice or request the tour dossiers, you can also chat with our team about the right travel insurance for you. Grade 1 – Introductory These trips involve walking for four to five hours per day or cycling for 15-50 km per day at a slow but steady pace. You will need a reasonable level of fitness and good health. Suggested Preparation 30 minutes of aerobic-type exercise (either road cycling or jogging), three times a week for three months leading up to your trip. Grade 2 – Introductory to Moderate These trips involve a combination of what is described in our Introductory and Moderate levels. The emphasis is on introductory activity but including several moderate stages. Grade 3 – Moderate These adventures involve walking for up to six hours per day or cycling for up to 65 km per day, at a steady pace. You will need a good level of fitness and be in good health. Suggested Preparation 45 minutes of aerobic-type exercise (road cycling or jogging) three times a week for three months leading up to your trip. Grade 4 – Moderate to Challenging This trip grading involves a combination of what is described in our Moderate and Challenging levels. The emphasis is on moderate activity but including several challenging stages. Grade 5 – Challenging These active holidays involve walking up to nine hours per day in mountainous terrain with steep ascents and descents, pass crossing & alpine weather conditions, or cycling for up to 80 km per day over undulating terrain, with some steep and sustained hills. You will need an excellent level of fitness, be prepared to carry a daypack weighing up to 8 kg and be completely comfortable in adverse weather conditions. Suggested Preparation 1 hour of aerobic-type exercise five times a week for three to six months leading up to your trip. We also recommend regular hill walking with a pack in variable weather conditions or road cycling.
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Route notes
While our tours vary in terms of difficulty, route finding is made simple and convenient with our specially prepared package of maps and route notes. On many of the walks it is easy enough to navigate carefully using the route notes provided with a cursory glance at the map. As holidays reach the higher grades, you will need to take more care and we would expect you to have at least some knowledge of using a compass. Maps for our tours also vary considerably, from up-to-date GPS referenced additions, to old map copies which may still be the only ones obtainable for a particular area. The differences in style, grade and destinations of our tours are features that make them of continual interest and delight to our walkers & cyclists. Each set of route notes can contain the following elements relevant to the route: History and information on the region and the route you are walking. Detailed maps including points of interest and accommodation. Detailed step-by-step descriptions (with pictures) of the route and information on detours/optional additions. Transport timetables and information for getting there and away. Safety information and advice. Contact details of accommodation, transport, local representatives and emergency support. Advice for things to do along the way. Suggestions for dining and self catering.
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How our self-guided holidays work
Self guided walking and cycling holidays offer freedom, independence and choice, allowing you to tailor your holidays in the UK & Europe to your interest and travel style. Our detailed Route Notes will contain all of the information you need to plan how you would like to approach each day, giving you the freedom to set your own pace. As you are not limited by the constraints of group travel, you are free to shorten or lengthen your walk as the terrain permits and can even take a day off, although you may need to travel onto your next accommodation by taxi or public transport in order to do so.
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Oct 31, 2025 - Nov 07, 2025Book with Confidence
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Low Deposit
Walkers' Britain requires a minimum deposit of 250 GBP per person or the full booking value, whichever is less, with the final balance not due until 70 days before departure.
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Cancellation Policy
We don't charge a cancellation fee, here is a summary of walkers' britain charges.
Up to 70 days before tour starts: Forfeit 100% of deposit.
At 69 days before tour starts: Forfeit 50% of booking price.
At 35 days before tour starts: Forfeit 100% of booking price.