Trails of Tuscany & Umbria
- Discover Tuscany and Umbria combining gentle walks with plenty of sightseeing
- Free time to explore the historic heart of Siena and world-class art in Florence
- Sample Tuscan wines and local delicacies during a vineyard tour and tasting
- The golden grasslands of the Val d’Orcia and the turquoise waters of Lake Trasimeno
- Short and scenic transfers to explore the best of these stunning regions on foot
Gallery
Itinerary
Day 1 Arrive in SienaArriving in the medieval city of Siena gives the feeling of having stepped back in time. At Siena’s heart is Il Campo; the central piazza and where the Palio horse race takes place twice every summer. After checking in at the hotel, why not head here for a coffee or glass of chilled wine and soak up the Italian ambience and relax into ‘la vita bella’.
On this slow-paced trip there are of course wonderful walks to take in the stunning Tuscan and Umbrian rolling hills, sprawling olive groves and vineyards, but also time to explore the iconic towns at your own pace. You have this afternoon and tomorrow morning free, so we recommend arriving early today to make the most of this first stop in the historical town of Siena.

Situated in Siena city centre, so perfect for exploring on foot. Built in around 1870 as a Neoclassical villa, it was restored in 2004, keeping its original style as well as its beautiful, frescoed common rooms. The comfortable bedrooms have air conditioning and WiFi access. Some have a balcony. The hotel has a restaurant, bar, terrace, and small garden to relax in.
Siena is a UNESCO World Heritage Site and one of Italy’s must-see attractions. The city is well-known for its wine and cuisine, art, museums, and Gothic architecture. Take time this morning to discover this charming historic town.
Why not add on the "Taste of Siena Food Tour" so you can eat your way through Siena’s hidden corners? Sample tastings of traditional delicacies, local wines, handmade pasta, olive oil and cheese as you walk through the historic centre (tour duration: 3 hrs, 10am start).
This afternoon, take the train (payable locally, approximately 1 hour duration) on a picturesque journey through classic Italian landscapes to Montepulciano. From the train station there is an included transfer to the hotel, where there will be a welcome meeting with our local supplier. The town is known for its red wine ‘Vino Nobile’, so perhaps relax with a glass this evening or purchase a bottle or two to bring home.

Our hosts offer a warm welcome to all guests to their extraordinarily charming B&B. Rooms are museum-like, decorated with period Italian antiques and frescoed ceilings while on the other hand there are renovated bathrooms with modern fittings. Each bedroom has a TV, fridge, and air conditioner.
This morning starts with an included transfer to Pienza. Pienza is said to boast the most delicious pecorino cheese in the whole of Tuscany—why not stop in at one of the shops and get some to take home? This UNESCO World Heritage town was commissioned by the pope in 1459 to the architect Bernardo Rossellino, with the task of designing the perfect town. Parts of the town were used in the filming of ‘The English Patient’, which was largely set in the nearby Sant’ Anna Monastery. Don’t miss taking a short walk along the wall on the south edge of town to take in the panoramic view.
On the walk back to Montepulciano it’s possible to visit one of the quaint cafes or stop for a picnic lunch in Monticchiello, a stunning hamlet with fortified walls.
Alternatively, instead of joining the walk today, there’s the option of relaxing and exploring the town of Montepulciano. The Church of Sant’Agostino is worth a visit as is the Palazzo Comunale, where it’s possible to climb the tall tower to get a view of the surrounding countryside. The historic Caffe’ Poliziano is an ideal lunch spot. Take a wander around the main square of Piazza Grande and the nearby Fortress of Montepulciano with its delightful gardens.
Ascent/Descent: 522m/464m

Our hosts offer a warm welcome to all guests to their extraordinarily charming B&B. Rooms are museum-like, decorated with period Italian antiques and frescoed ceilings while on the other hand there are renovated bathrooms with modern fittings. Each bedroom has a TV, fridge, and air conditioner.
Leaving Montepulciano, on a half-day walk through the iconic Tuscan countryside of yellow fields and hilltop villages to Acquaviva. From here a transfer is included to Cortona, where it’s easy to find a quiet spot to relax in the Tuscan sun and read a good book or enjoy watching the world go by.
Alternatively, there is the option to do a longer full-day walk continuing from Acquaviva to Valiano and then transferring from here to Cortona.
Cortona, located at 600m altitude, is characterised by steep narrow streets and medieval architecture. Pay a visit to the distinguished Etruscan Academy Museum, founded in 1727, or simply enjoy the expansive views from the Piazza Garibaldi.
Montepulciano to Acquaviva: 9km (6 mi). Ascent/Descent: 37m/269m
Acquaviva to Valiano: 7km (4.5mi). Ascent/Descent: 3m/49m
Combined: 16km (10mi). Ascent/Descent: 40m/318m

Hotel San Michele is located inside one of Cortona’s oldest buildings, Baldelli Palace, a beautifully restored 15th-century mansion located right in the heart of Cortona. It has even been declared a national monument by the Ministry of Art. It's just a few steps from the main squares, restaurants and attractions of the town.
The day begins with a short (10-minute) transfer to Ossaia, which is the starting point for the walk to Tuoro. The walk provides spectacular views over the Valdichiana Valley and Lake Trasimeno. This historical location is where Hannibal’s Carthaginian warriors ambushed the Roman Army in 217 BC at the Battle of Lake Trasimeno.
Crossing into Umbria at the village of Tuoro, where there are several lovely shops and a café to quench your thirst. A transfer (20 minutes long) will be provided to the medieval village of Castel Rigone, with its late 15th-century church.
Ascent/Descent: 307m/326m

Relais La Fattoria is a restored 17th-century hilltop farm overlooking Trasimeno lake. It has 30 luxurious rooms, a swimming pool, a well-stocked wine cellar and a panoramic terrace.
Today begins with a short transfer (30 minutes) to the Mongiovino Abbey – ‘Madonna di Mongiovino Sanctuary’. From here the walk commences to the charming medieval hilltop village of Panicale. Before setting out, pay a visit to the Renaissance-era abbey and follow the path up to also visit Mongiovino Castle.
It’s easy terrain to Panicale and there’s the chance to take a short detour to the peaceful little Lupaia Lake along the way. This is an additional 2.3km/1.4mi, making the overall walk 9.1km/5.7mi.
Panicale has a nice square with a café where it’s possible to enjoy a light lunch and a glass of local wine. From Panicale there is an included transfer to the accommodation, which takes around 30 minutes. The next 2-nights will either be in Poggio delle Corti or Solomeo.
Mongiovino Abbey to Panicale: 7km (4mi). Ascent/Descent: 228m/124m
Mongiovino Abbey to Panicale with detour to Lupaia Lake: 9km (5.5 mi). Ascent/Descent: 324m/219m

Borgo Mandoleto is a comfortable agriturismo in Solomeo, sourrounded by ancient oak trees and the Perugian hills. Relax in its well-kept garden or enjoy the swimming pool and spa facilities during your stay. The rooms have been tastefully decorated with classic finishes and wood-beamed ceilings. Donnatella is a wonderful cook, the restaurant serves her authentic local cuisine in an elegant dining room with a fireplace.
There’s an included transfer to Cibottola Castle (taking around 10 minutes) or alternatively to Monte Vibiano Winery (approximately 20 minutes’ drive). If the chosen drop-off point is Cibottola Castle, then there’s the chance to visit here before walking to the winery. The walk to the vineyard is an additional 4.5km/3mi, making the total walk today 15.5km/9.5mi.
At Monte Vibiano Winery there’s an included tour of the vineyard by electric car or e-bike and a wine tasting to sample the local varieties.
The walk from the winery to Poggio delle Corti is a peaceful and relaxing stretch, along an almost-flat path, which traces the Nestore River Park. There is a transfer back to the accommodation at the end of the walk if staying in Solomeo.
Cibottola Castle to Monte Vibiano Winery: 4.5km (3mi). Ascent/Descent: 3m/265m
Monte Vibiano Winery to Poggio delle Corti: 11km (7 mi). Ascent/Descent: 62m/35m
Combined: 15.5km (9.5mi). Ascent/Descent: 65m/300m

Borgo Mandoleto is a comfortable agriturismo in Solomeo, sourrounded by ancient oak trees and the Perugian hills. Relax in its well-kept garden or enjoy the swimming pool and spa facilities during your stay. The rooms have been tastefully decorated with classic finishes and wood-beamed ceilings. Donnatella is a wonderful cook, the restaurant serves her authentic local cuisine in an elegant dining room with a fireplace.
After a transfer to Monte Tezio (approximately 40 minutes’ drive) the walk begins to Perugia along a historic route. It goes through the Tezio area—an important location in the Middle Ages as it was the source of drinking water for the city. It is still possible to see remnants of the ancient aqueducts.
Perugia’s huge Etruscan arch gate welcomes travellers to the capital of Umbria. Crossed by the River Tiber, Perugia is home to the Palazzo dei Priori, which looms above the main piazza. The city is home to some of the best museums in Umbria, including the Galleria Nazionale dell’ Umbria. There’s also the chance to wander through the markets, shops, and arcades of this enchanting city.
There are two options for today’s walk. The distances shown are based on the shorter walking route. This walk goes from Mount Tezio to San Marco village, just outside Perugia. There’s then a short 10-minute transfer to the Monte Ripido Convent at the entrance to Perugia. After time to visit the convent, walk from there into the city centre. By taking this transfer it shortens the route which is a trickier hilly section on asphalt. If preferred, then the walk directly into the city is possible (without the transfer).
Monte Tezio to San Marco (Part 1): 13.5km (8.5mi). Ascent/Descent: 218m/330m
Monte Ripido Convent to Perugia (Part 2): 2km (1.5mi). Ascent/Descent: 32m/44m
Combined: 15.5km (9.5mi). Ascent/Descent: 250m/374m

Exclusively located in the heart of the historical centre of Perugia, Hotel Fortuna is housed in a building that dates from the 1300s and still boasts numerous original features.
Feel like a local and discover the food and wine scene of Perugia by booking an additional experience called the "Taste of Perugia Food Tour" (duration: 3,5 to 4 hrs, 10am start). Then catch a direct train, speeding through photogenic Italian landscapes, to Florence’s Santa Maria Novella Station (takes approximately 2 hours 15, payable locally). Or if you prefer, you could get an early train to Florence.
Upon arrival in Florence, known as ‘The Athens of the Middle Ages’, there is then time at leisure to explore this incredible historic city. Immerse yourself in the wonders of Florence there is the option of doing a circular walking loop taking in Florence’s top attractions. Discover Palazzo Vecchio, the infamous fortress, and Florence Town Hall, navigate Accademia Galleria for Michelangelo’s “David,” and be awed by the huge exterior of Florence’s Cathedral “Duomo.”
Ascent/Descent: 114m/114m

Stay at the 3-star Boutique Hotel Del Corso. Amid shops on a narrow street in the city centre, this relaxed hotel is a 5-minute walk from the Gothic landmark Florence Cathedral.

Stay at Hotel della Signoria in the heart of Florence, a few steps from Piazza della Signoria square and the famous Ponte Vecchio bridge. Enjoy breakfast with a view from its terrace in the morning which is located on the 7th floor.
From Florence it’s easy to take a day trip to Pisa as it is only an hour’s journey between the two cities (please contact us if you would like to add a night here).
Check out of the hotel and continue with onward journey.
Other Information
Is it for me?This is the perfect trip for discovering the quiet trails, iconic scenery and highlights of Tuscany and Umbria. The itinerary has a mix of gentle walks that allow you to travel at a slow pace, with plenty of free time to enjoy the incredible towns and villages along the way.
Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.
Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.
Solo Travellers
As a guide, we would suggest that the minimum age of traveller this holiday would be suitable for is: 10 Years
With up to 15km (9 mi) of walking each day, this trip is graded easy to moderate and is suitable for those with a good level of fitness. We suggest that you should train by walking some walks of similar daily distances to your planned itinerary. The landscape is undulating with gentle ascents and descents, with the exception of the walk from Pienza to Montepulciano on Day 3 which has an ascent of 522m (1712ft). The elevation on other days rarely exceeds 200-300m (650-950ft).
On most days there is a choice of walks and other activities such as sightseeing, wine tasting or optional food tours so that you can enjoy this trip at your own pace, please view the itinerary for more details.
During the summer, temperatures are high, and you will need to carry plenty of water with you (additional weight), which may slow you down. Most of the route follows dirt tracks and gravel paths although you will occasionally be following minor paved roads.
This route is suitable for most regular walkers of average fitness. You should train by walking some daily walks of similar daily distances to your planned itinerary.
You will be staying in charming bed and breakfast accommodations and 3-4* hotels. We specifically choose the properties to ensure that you enjoy every minute of your stay. All offer a warm Italian welcome to walkers and traditional hospitality.
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. We will confirm your accommodation details upon confirming your reservation.
Single Rooms
If you require single rooms for your party we will of course try to accommodate your request, subject to availability and payment of a single supplement. This independent walking holiday is also available to solo walkers.
Additional Nights
You may wish to take some extra nights along the route, either to rest or for those with plenty of energy to explore some of the other walking opportunities nearby. Please let us know if this is of interest and we can help organise this for you.
Meals
The delicious Italian food and wine available locally are undoubtedly a highlight of this tour. The price of your trip includes breakfast each morning. Dinners are included during your stay at Borgo Mandoleto in Solomeo (Days 6 and 7), as well as a wine tasting (Day 6). Lunches and other dinners are not included so you are free to choose from the available options.
Food Tours
If you are looking to fully immerse yourself in the Tuscan culture by sampling local delicacies, then the Food Tours in Siena and Perugia are for you. These guided experiences can be added to your booking (at an additional cost) and take you on a short and gentle walk through the historic centre with plenty of time for side visits. If you are interested, please let us know at the time of booking so we can organise this for you.
The routes are partially waymarked and for the most part easy to follow. Navigation is straightforward as you can use the Macs Adventure Smartphone App which has maps, directions, GPS tracks, and daily route information. Simply download the GPS tracks for offline use and follow the route on your phone with the assurance that navigation will be simple, and you can’t get lost.
You will find more information on downloading the app in your Macs Adventure Account.
- 9 Nights accommodation in B&B accommodation and 3-4* hotels
- 9 Breakfasts
- 2 Dinners
- Wine tasting (Day 7)
- Transfers as per itinerary (Days 3, 4, 5, 6, 7 and 8)
- Baggage transfers (Days 4, 5, 6 and 8)
- A detailed information pack and welcome meeting (Day 2)
- Access to the GPX tracks and route information via the Macs Adventure smartphone app
- 24/7 Emergency telephone support
- Travel to Siena and from Florence
- Train from Siena to Montepulciano Stazione (Day 2)
- Train from Perugia to Florence (Day 9)
- Travel Insurance
- Personal Equipment
- Lunches, drinks, snacks and all other dinners
- Local tourist taxes (if applicable)
- Additional nights before, during or after the trip
- Taste of Siena Guided Tour (Day 2)
- Taste of Perugia Guided Tour (Day 9)
This tour is available to start anytime between April to October, and possibly March, but we will need to check for you that the hotels have opened for the season as several in Tuscany only open at Easter, so it depends when this falls and if they have decided to open sooner.
April, May and June are normally pleasant temperatures for walking and the vegetation is particularly lush at this time of year. May is when most wildflowers are coming into bloom. 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 and carry a lot of water (additional weight) with you, although the towns and villages are buzzing at this time of year, which is great.
Peak Season Availability
Early booking is recommended to secure the best choice of accommodation for you throughout the peak spring and summer months. We may require some flexibility regarding your dates, accommodation and/or itinerary. We will do our best to provide a suitable alternative in line with our usual tour. In the instance that our usual accommodation is not available, a supplement for alternate accommodation may be payable, but will of course be discussed with you. We will always try our best to get you confirmed on the date you wish to travel.
Florence and Pisa are the nearest airports to the start of your trip in Siena, Tuscany. You can easily catch a train to Siena which has a duration of roughly 2h20m from Florence, or 2h30m from Pisa. Visit Trenitalia for times and prices, the tickets can be purchased on arrival or online prior to departure. If you are travelling from elsewhere in Italy, the train is a great choice as it is efficient and relatively inexpensive.
From the final destination of your trip in Florence, you can easily get a local bus or taxi to Florence Airport. The airport is located in the northwest of the city, only about 8km from the centre, meaning the duration of your journey there will only take approx. 15 to 25 minutes.
If you are flying from Pisa, then there is a direct bus (duration: 70 minutes) connecting Florence and Pisa Airports. Alternatively, you can take the train from Florence to Pisa (2h30m). From Pisa city centre you can take the quick PisaMover bus to the airport which is only 1km away, located near the coast (approx. 8 minutes).
Visit Trenitalia for times and prices, the tickets can be purchased on arrival or online prior to departure. If you are travelling from elsewhere in Italy, the train is a great choice as it is efficient and relatively inexpensive.
When required your bags will be transferred from your hotel and moved onto your next overnight accommodation. This is on Days 4, 5, 6 and 8. When you are travelling with public transport, you will need to take your luggage with you. 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. 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, a day pack, sun hat, and sunscreen.
It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity, emergency evacuation and hospital care.
You can use public transport or local taxis to continue to your next overnight stop.
This walking holiday is graded easy to moderate and involves 2.5-4 hours of walking each day so you should enjoy an active lifestyle to get the most from this holiday. 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 Italy is sublime and April, May and June are absolutely lovely. Autumn is probably my 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 early to miss the heat of the day, although the towns and villages are buzzing which is great. You can view weather details for the region here.
We suggest you book as soon as your plans are finalised; Tuscany and Umbria are extremely popular especially during July/August. You will find up to date availability on our website and we will always try and accommodate your plans so just ask.
You will need good walking shoes/boots, comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc.
When required your bags will be transferred from your hotel and moved onto your next overnight accommodation. This is on Days 4, 5, 6 and 8. When you are travelling with public transport, you will need to take your luggage with you. We ask you to limit your luggage to one bag of up to 20kg per person.
Either Pisa, Florence or Rome are convenient and you can reach the start/end of the walk by train in an hour or two.
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