Self Guided Walking Holidays & Cycling Holidays


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Self guided walking tour in Tuscany and Umbria
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Highlights

  • Walking in Tuscany and Umbria; hill-top towns, Siena, Perugia and on to Florence.
  • Renaissance Florence— the Uffizi Gallery, Pitti Palace, boutiques and cafés.
  • Siena, a UNESCO World Heritage site with its Il Campo central piazza.
  • Trails through vineyards, olive groves and cyprus-lined rolling hills.
  • Wine tasting and optional cooking classes in Umbria.

Explore the absolute best of Tuscany and Umbria on foot; starting with the medieval and Renaissance hill-top towns of Siena and Pienza, on to historic Perugia and ending in iconic Florence. Nestled in the green heart of Italy, you’ll walk through landscapes of rolling hills, past soldier-straight lines of cyprus trees, through vineyards and olives groves.

Begin your journey in the UNESCO World Heritage city of Siena, then it's on to Tuscany's Renaissance hill-top towns - Montepulciano, Montefollonico/Pienza, Montichiello. In Cortona stay in a 15th century mansion, high up on a hill. Trails in south Tuscany afford panoramic views over the olive groves, yellow plains and vineyards of the Valdichiana valley and Lake Trasimeno. Crossing into Umbria, stay at a quaint villa and country inn, with a wine tasting and optional cooking lesson. Immerse yourself in Perugia's fascinating museums, markets and arcades before finally arriving in Florence, with time to discover this incredible city.

DAY 1: Arrive Siena

Arrive in the medieval city of Siena, where you will feel as if you are stepping 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 your hotel, head here for a coffee or glass of chilled wine and let yourself soak up the Italian ambience and relax into ‘la vita bella’.


Overnight: Hotel Chiusarelli***, Siena


3-star Hotel Chiusarelli is found inside the old city walls and occupies an impressive neo-classical villa built in the 1860s; the perfect base from which to explore.


DAY 2: Free time in Siena. Travel to Montepulciano

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 explore this charming historic town.


This afternoon, take the train (payable locally, approx.1hr duration) on a picturesque journey through classic Italian landscapes to Montepulciano, from where you will receive a transfer to your hotel, for your welcome meeting.


Overnight: L’Agnolo B&B, Montepulciano


Located in the heart of Montepulciano, this once grand home is now a beautiful small B&B, still displaying the ornate high fresco ceilings. Expect a warm welcome during your stay in this unique bed and breakfast property.


DAY 3: Choice of Loop Walks: Montefollonico or Pienza and Montichiello

Option 1: Transfer to Montefollonico, an amazing village with terrific views over the Valdichiana. Take a relaxing stroll through vineyards and olive groves. Walk: 14 km (3h30)


Option 2: Transfer to Pienza, a village said to boast the most delicious pecorino in the whole of Tuscany—why not stop in at one of the shops and take some home! On your return walk to Montepulciano you will come across Montichiello, a stunning hamlet with fortified walls. Montichiello is the ideal spot to rest and enjoy a lovely lunch. Walk:15 km (4-4h30)


Overnight: L’Agnolo Bed and Breakfast, Montepulciano



DAY 4: Half-day Walk to Acquaviva. Transfer to Cortona


Leaving Montepulciano, walk a short distance through the iconic Tuscan countryside of yellow fields and hilltop villages to Acquaviva. At around 12h30-13h00 take a transfer to Cortona, where you can find a quiet spot and relax in the Tuscan sun or perhaps a shady place.



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.


Walk: 10km (2h30 approx.)


Overnight: Hotel San Michele****, Cortona



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.



DAY 5: Walk Ossaia to Tuoro. Transfer to Castel Rigone


Your day begins with a short (10 mins) transfer to Ossaia, where you start your walk to Tuoro. You’ll be walking with spectacular views over the Valdichiana Valley and Lake Trasimeno, scene of Hannibal's ambush of the Roman Army in 217 BC (Battle of Lake Trasimene).



Cross into Umbria at the village of Tuoro, where there are several lovely shops and a café to quench your thirst. A transfer will take you onwards (20 mins) to the medieval village of Castel Rigone, with its late 15th century church.


Walk: 16km (4h30-5hrs)


Overnight: Villa Mina B&B, Castel Rigone



Friendly Villa Mina boasts just three rooms, and guests can enjoy the lovely gardens and pool.



DAY 6: Panicale and Mongiovino Abbey & Castle


A 30 mins transfer brings you to Castello di Mongiovino, from where you will walk to the charming hill-town of Panicale. Before you set out, pay a visit to the Renaissance Mongiovino Abbey, before following the path up to the castle. Its easy terrain to Panicale; a picturesque medieval village with a nice square and café where you can enjoy a light lunch and a glass of good local wine. At 14h00 approx. take a transfer (30 mins) to your accommodation at la Corte del Poggio, a highlight of your Italian adventure.


Walk:12km (3hrs approx.)


Overnight: La Corte del Poggio (incl dinner) At La Corte del Poggio, not far from Perugia, you will stay in a charming old stone house. It is possible to book a cooking class (arranged and paid for locally). Dinner is included during your stay.



DAY 7: Monte Vibiano and Wine Tasting


A car will transfer you to Monte Vibiano (20 mins) where you will visit the vineyards (touring by electric car) and enjoy the delights of the region with a wine tasting.



Return on foot to your accommodation at La Carte del Poggio—a peaceful and relaxing stretch along an almost-flat path which traces the Nestore River Park.


Walk: 13km (4hrs approx.)


Overnight: La Corte del Poggio (incl dinner)



DAY 8: Monte Tezio. Walk to Perugia

After a transfer to Monte Tezio (approx. 40 mins) start your walk to Perugia along a historic route which leads to 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 acqueducts.


Perugia's huge Etruscan arch gate welcomes you to the capital of Umbria. Crossed by the River Tiber, Perugia is home to the Palazzo dei Priori, which looms above the main piazza. Here you will find some of the best museums in Umbria, including the Galleria Nazionale dell’ Umbria. Wander the markets, shops and arcades of this enchanting city.


Walk: 17km (5hrs approx.)


Overnight: Hotel Fortuna***, Perugia


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.



DAY 9: Train to Florence. Time to explore


Today you catch the train direct to Florence’s Santa Maria Novella station (approx. 2h15, payable locally), speeding through photogenic Italian landscapes.
Upon arrival in Florence, known as ‘The Athens of the Middle Ages’, make your own way to your hotel, then enjoy time at leisure to explore this incredible historic city.


Overnight: Hotel La Fortezza***, Florence



Hotel La Fortezza is located in a quiet area, conveniently close to the Santa Maria Novella train station and within easy reach of Florence’s highlights.


DAY 10:
Visit Pisa or Onward Travel

From Florence you can easily 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 your hotel and continue your onward journey.


Extensions


Why not extend your time in Italy with a few nights in Florence or Pisa? Please contact us to make arrangements.

Accommodation

You will be staying in charming bed and breakfast accommodation 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, traditional hospitality and delicious local food and drink.


Accommodation Details

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. Alternative details will be noted on your accommodation sheet. We will confirm your accommodation details on confirming your reservation.


Single Rooms

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. This independent walking holiday is available to solo walker and a solo walker supplement is payable, as costs are not shared with another person. 


Meals

The delicious Italian food and wine available locally is undoubtedly a highlight of this tour. The price of your trip includes breakfast each morning. Dinners are included during your stay at La Corte del Poggio, as well as a wine tasting. Lunches and other dinners are not included so you are free to choose from the available options.


Some hotels will provide a packed lunch on request, but often the best option is to stop at a local café or restaurant en-route or buy a picnic lunch at the local shop. Dinner is available either at your hotel or nearby.


Baggage 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.



Equipment

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.


Recommended Reading


Tuscany & Umbria—Lonely Planet Regional Guides


Under The Tuscan Sun—Frances Mayes


Walking and Eating in Tuscany & Umbria—James Lasdun & Pia Davis


Additional Nights

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.



 

 

 




Hotel Fortuna - Perugia


Exclusively located in the heart of the historical centre of Perugia, Hotel Fortuna is housed in a building that dates from the 1300’s and still boasts numerous original features.


 

 

 


 

 

 



Hotel Chiusarelli - Siena



Hotel Chiusarelli - Siena

3-star Hotel Chiusarelli is found inside the old city walls and occupies an impressive neo-classical villa built in the 1860s; the perfect base from which to explore.


 

 

 


 

 

 



L'Agnolo B&B - Montepulciano



L'Agnolo B&B

Located in the heart of Montepulciano, this once grand home is now a beautiful small B&B, still displaying the ornate high fresco ceilings. Expect a warm welcome during your stay in this unique bed and breakfast property.


 

 

 


 

 

 



Hotel San Michele - Cortona



Hotel San Michele - Cortona

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.


 

 

 


 

 

 



Villa Mina B&B - Castel Rigone



Villa Mina B&B - Castel Rigone

Friendly Villa Mina boasts just three rooms, and guests can enjoy the lovely gardens and pool.


 

 

 


 

 

 



Hotel La Fortezza - Florence



Hotel La Fortezza - Florence

Hotel La Fortezza is located in a quiet area, conveniently close to the Santa Maria Novella train station and within easy reach of Florence’s highlights.


 

 

 


 

 

 



La Corte del Poggio - nr Perugia



La Corte del Poggio - Country House

At La Corte del Poggio, not far from Perugia, you will stay in a charming old stone house. It is possible to book a cooking class (arranged and paid for locally) - Cristina and her niece will share with you the secrets of Italian cuisine so that you can replicate the very best simple recipes in your own home. Dinner is included during your stay.


 

 

 

Availability

Our Treasures of Tuscany & Umbria self-guided walking tour is available from April to October. You can start your holiday on any date in the season.


Time of Year

Spring in Italy 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 walking early to miss the heat of the day, although the towns and villages are buzzing, which is great. 


Single Rooms & Solo Walkers

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. This independent walking holiday is available to solo walkers and supplement is payable, as costs are not shared with another person.  


Grade & Terrain

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 night's accommodation.   


Navigation, Route Notes & Maps

The route is not waymarked but we supply detailed maps and route notes so you will have no problem following the route. 


Baggage Transfers

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.



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. 


General Information

The distances and ascents/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and trousers), sun hat and 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 Siena

We recommend flying to Florence and then catching the train to Siena (train takes 1h30). Tickets can be purchased on arrival or online prior to departure.


Visit www.trenitalia.it for times, prices and booking.


Getting from Florence

From Florence, buses and taxis connect the city centre to Florence Airport and take 25 or 15 mins respectively (costing 4.5/20EUR approx.).


If you are flying from Pisa, then a direct bus (70 mins) connects Florence and Pisa Airports, or you can take the train.


From Pisa city centre, take the PisaMover bus the 1km to Pisa Airport (8 mins).

Included

  • 9 Nights accommodation in B&B accommodation and 3-4* hotels.
  • Transfer from Montepulciano Stazione to accommodation on Day 2, followed by welcome meeting.
  • 9 Breakfasts.
  • 2 Dinners at La Corte del Poggio.
  • Wine tasting on Day 7.
  • Transfers as per itinerary on Days 3, 4, 5, 6, 7 and 8.
  • Baggage transfers on Days 4, 5, 6 and 8.
  • A detailed info pack, route notes and map.
  • 24-7 Emergency telephone support from our local office in the event of a problem.

Excluded

  • Travel to the start (Siena) or from the finish of the tour (Florence).
  • Train travel on Days 2 and 9.
  • Lunches, dinners, snacks and drinks.
  • Travel Insurance.
  • Personal Equipment.
  • Taxi transfers or public transport should you need to skip a stage.

Extras

  • Solo walker or single room supplement.
  • Extra nights before, during or after your walk.
  • Private transfers.

How fit do I need to be?

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 night's accommodation. 

When is the best time of year?

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.

How far in advance do I need to book?

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.

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.

How do the baggage transfers work? 

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.

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. 

What happens if I am unable to walk a stage?

You can use public transport or local taxis to continue to your next overnight stop. 

Walking through a postcard!

5

I love the self guiding nature of this type of trip. A girlfriend and I did this walk in September. It was still hot and humid. You need to always carry water and refill in villages. We are in our late sixties and we loved it. Walking poles helped on the dirt roads and hills and rough dry creek beds. The views were incredible and we felt we really were walking through a picture post card.

Pinky

Sydney

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Seemless

5

We really had no idea what to expect when we booked this trip but we were so happily surprised. Not having having to worry about booking everything ourselves was wonderful and all of the accomodations were very nice. We were always expected and welcomed at the end of our walks and our suitcases were waiting for us. So easy. The local guides (hello Beppe and Michele!) that shuttled us around were on time, organized and very helpful (and willing to be more helpful if we ever got lost or wanted to switch things up, which thankfully we didn't). The walking instructions were very clear and easy to follow and took us on some of the most beautiful scenic walks of Tuscany and Umbria. We got lost a couple of times but it was minor and just added to the adventure. Easy to backtrack to pickup a previous route note. And if you don't like the crowds -- we'd often go hours walking without even seeing a local. Truly off the beaten path. All in all a fabulous vacation that kept us away from the crowds and allowed us to see Italy from a new perspective. An awesome way to travel.

Mike and Ann

Vancouver

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Outstanding service

5

This was our fourth summer vacation arranged by Macs Adventure, after Guernsey 2012, the Cotswolds Way 2013 and the South West Coastal path from Padstow to Penzance in 2014. As always, everything was well arranged. This year was very special because my wife had a foot surgery three weeks before we left for Italy meaning she was unable to walk together with me. We asked Beppe from Viadelsole, Macs' Italian partner, if she could go from place to place together with the luggage, "Of course, no problem" was the answer! On the second day of walking, my wife tried to join me but had to give up after 4km, so I called Beppe who then picked us up and drove us to the destination. On two other occasions, when I was behind schedule, I was picked up by Michele or Beppe without calling for help and brought to the destination. On one other occasion we changed an afternoon walk after a wine tasting into a restaurant visit at the shores of lago Trasimeno. Michele arranged for a table, and drove us to and from the restaurant. Finally I want to thank Giulia and Christina at La Corte del Poggio for letting us in to their home. We had splendid food and talks about food and other interesting things. One last thing, don't do it in July and August as we did. It's hot, 37C at the worst. Florence is filled, waiting for 3-4 hours is not unusal. Go in April or September.

Knud

Copenhagen, Denmark

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Tuscany and Umbria

4

Hello, First of all, the local tour-operator did a great job, everything was well organized, on time and so on. they are really friendly, ready to help and I will thank them very much . The only black point was the breakfast in Montepulciano, it had to be taken outside and the Cafe Poliziano was horrible. we met american fellows and they had the same vue on it. the first breakfast, i said to myself OK maybe i didn't explain it correctly but on the second day, the same bad impression, they see you as a tourist (mean in the bad way). it's the first time that I write such a review but it has to be said. What a difference with the lovely and superb accomodation in the same town. it's not my mother language but hope you understand it well. bye nice day to all of you

Patrick

Brussels

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We would recommend this walk.

5

The walks were relaxing and the villages interesting. We had a few problems with the instructions, especially left and right turns and before and after specific physical features or buildings. You need to combine the instructions with your own assessment of the landscape and features such as crops, buildings etc. The staff were excellent and accommodation comfortable. It is important to be aware of the weather conditions over the duration of the walk each day.

The Forward Scout

Adelaide SA

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Treasures of Tuscany & Umbria

4.8 5

100.0

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