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Treasures of Tuscany & Umbria

10 Days & 9 Nights 4.9 Read 7 reviews
  • 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.
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What To Expect

This tour is perfect for culture vultures who enjoy fantastic walking and incredible food and wine. Walk the highlights of Tuscany and Umbria, visiting medieval and Renaissance villages, towns and cities. Short transfers mean you’ll discover the very best of these stunning regions on foot.

Trip Style:

Self Guided | Go at your own pace on an independent holiday.


Multi Centre Walking | You will spend multiple nights in one or more of the locations on this walking holiday

This trip is suitable for:

First Timers

Ideal if you have an interest in:

  • Foodie Adventures
  • Wine, Whisky & More...

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.   


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

Accommodation Information

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. 


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.

  • 9 Nights accommodation in B&B accommodation and 3-4* hotels
  • 9 Breakfasts
  • 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
  • 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
  • Extra nights before, during or after your walk
  • Private transfers

When To Go

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.

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. 

Getting to the Start

We recommend flying to Florence or Pisa 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 the End

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).

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.

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. 


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.

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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Day 1 Arrive Siena Day 2 Free time in Siena. Travel to Montepulciano Day 3 Choice of Loop Walks: Montefollonico or Pienza and Montichiello 9 miles / 15 km Day 4 Half-day Walk to Acquaviva. Transfer to Cortona 6 miles / 10 km Day 5 Walk Ossaia to Tuoro. Transfer to Castel Rigone 10 miles / 16 km Day 6 Panicale and Mongiovino Abbey and Castle 7 miles / 12 km Day 7 Monte Vibiano and Wine Tasting 8 miles / 13 km Day 8 Monte Tezio. Walk to Perugia 11 miles / 17 km Day 9 Train to Florence. Time to explore Day 10 Visit Pisa or Onward Travel

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