Trails of Tuscany & Umbria

10 Days & 9 Nights 4.9 Read 10 reviews
  • 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
Combine the medieval towns and Renaissance cities of Tuscany with the untouched landscapes of Umbria, and you have all ingredients for a perfect slow adventure in Italy. Quiet trails lead through rolling hills connecting olive groves with vineyards and bustling local markets. Work up an appetite and follow the scent of fresh thyme and garlic as you hunt for your next lunch spot. These regions are known for their sensational slow food movement and locally produced wines which you can sample during a vineyard tour. This trip is a perfect mix of manageable walks and lots of sightseeing whilst staying in ideally located hotels and authentic B&Bs to allow you to make the most of your visit.
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.

Tour Type:

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.

This trip is suitable for:

Solo Travellers

As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 10 Years

Ideal if you have an interest in:

  • Foodie
  • Wine

Activity Level & Terrain

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.


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.

Experience & Fitness

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.


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. 

  • 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
  • Lunches, drinks, snacks and all other dinners
  • Personal equipment
  • Additional nights before, during or after the trip
  • "Taste of Siena" Guided Food Tour (Day 2)
  • "Taste of Perugia" Guided Food Tour (Day 9)
  • Local tourist taxes (if applicable)

When To Go

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.

Getting to the Start

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.

Getting from the End

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.

Luggage Transfer

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.

General Information

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.

Travel Insurance

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. 

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Recommended Reading
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Day 1: Arrive in Siena Day 2: Free time in Siena; travel to Montepulciano Day 3: Walk from Pienza to Montepulciano; or free time in Montepulciano 9.5 miles / 15.5 km Day 4: Half day walk from Montepulciano to Acquaviva; transfer to Cortona 6 miles / 9 km Day 5: Walk from Ossaia to Tuoro; transfer to Castel Rigone 8 miles / 12 km Day 6: Transfer to Mongiovino Abbey; walk to Panicale 4 miles / 7 km Day 7: Transfer to Monte Vibiano for a wine tasting; walk to Poggio delle Corti or Solomeo 7 miles / 11 km Day 8: Transfer to Monte Tezio; walk to Perugia 9 miles / 15 km Day 9: Train to Florence; free time to explore or take a circular walking tour 4 miles / 6 km Day 10: Onward Travel

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