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Trails of Tuscany

8 Days & 7 Nights 4.9 Read 12 reviews
  • Soak up the Tuscan charm on a self-guided slow adventure trip in Italy
  • Live like a Florentine and take an evening stroll to Ponte Vecchio in Florence
  • Sample Tuscany's culinary traditions, world-class wines, and seasonal foods
  • Enjoy an aperitivo at Il Campo in Siena's heart, soaking up the Italian ambience
  • Views to Lake Trasimeno from Piazza Garibaldi in the medieval town of Cortona
With its golden landscape dotted with ancient wine-making villages, olive groves, and rows of Cypress trees, Tuscany is best explored on foot. This is an authentic experience exploring the quiet trails, iconic scenery, and highlights of Tuscany. Travel at your own pace through the rolling countryside and visit medieval walled towns and hilltop villages along the way. Visit Renaissance cities and enjoy free time to immerse yourself in the local culture and traditions. Florence feels like a living museum filled with world-class art and architecture, and walking through Siena's city gates feels like stepping back in time. Paired with incredible food, this is a slow adventure that we know you're going to love.
This is the perfect trip for discovering the quiet trails, iconic scenery, and highlights of Tuscany. 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. Tuscany is not only a feast for the eyes, sample pecorino cheese in Pienza, Pasta al Fumo in Cortona, and relax with a glass of 'Vino Nobile' in Montepulciano.

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. 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. 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).

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.


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. Lunches and other dinners are not included so you are free to choose from the available options.

Siena Food Tour

If you are looking to fully immerse yourself in the Tuscan culture by sampling local delicacies, then a Food Tour in Siena is 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. 

  • 7 Nights accommodation in B&B accommodation and 3-4* hotels
  • 7 Breakfasts
  • Transfers as per itinerary
  • Baggage transfers
  • 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
  • Lunches, drinks, snacks and all other dinners
  • Local tourist taxes (if applicable)
  • Travel to Siena and from Florence
  • Train from Siena to Montepulciano Stazione (Day 2)
  • Travel Insurance
  • Personal Equipment
  • Additional nights before, during or after the trip
  • Taste of Siena Guided Tour (Day 2)

When To Go

Our Trails of Tuscany self-guided walking tour is available to book from April to October and you can start your holiday on any date in the season.

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. 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.

What happens if I become ill or can’t walk a stage?
Which is the best airport?
How do the luggage transfers work?
What personal equipment do I need?
Recommended Reading
How far in advance do I need to book?
How fit do I need to be?


Day 1 Arrive in Siena Day 2 Free time in Siena; travel to Montepulciano Day 3 Walk from Pienza to Montepulciano 9.5 miles / 15.5 km Day 4 Montepulciano to Acquaviva; transfer to Cortona 6 miles / 9 km Day 5 Free time in Cortona or half-day walking tour 8 miles / 13 km Day 6 Train to Florence; half-day walking tour 4 miles / 6 km Day 7 Free time in Florence Day 8 Visit Pisa; onward travel

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