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Treasures of Tuscany & Umbria

10 Days & 9 Nights 4.9 Read 7 reviews
  • Walk from the rolling vineyards of Tuscany and into the green heart of Umbria
  • Bask in the sun and villas of Cortona as in the famous book and movie, “Under a Tuscan Sun”
  • Hike through the golden grasslands of the Val d’Orcia to the turquoise waters of Lake Trasimeno
  • Forage for truffles, savor Sangrantino wines and cross the River Tiber to the artistic legacy of Perugia
  • Enjoy short, scenic transfers to discover the very best of southern Tuscany and Umbria on foot
Enjoy the best of Tuscany and the treasures of Umbria on foot, walking from the iconic hilltop towns of Southern Tuscany, into the untouched landscapes of Umbria and to the final highlight of the Renaissance city of Florence. Staring in Siena, walk through the Val d’Orcia to the hilltop towns of Montepulciano, Pienza, and Montichiello. Wander through landscapes of rolling countryside, rows of Cyprus trees and bountiful olive groves until you reach Cortona, the setting for the popular book and movie, Under a Tuscan Sun. Cross into Umbria and walk the tranquil paths to Perugia, the capital of Umbria, to immerse yourself within the fascinating museums, bustling markets and unspoiled cultural delights. Toast to your active adventure upon the rooftop terrace of your historic hotel overlooking Florence in celebration of your pilgrimage from Tuscany to Umbria.
This tour is perfect for active walkers who want to explore the delights of Tuscany and the highlights of Umbria, for an unforgettable Italian getaway. Enjoy fantastic walking, delectable food and wine, exploring Renaissance villages and relaxing in local hotels and B&Bs. Daily walks are graded easy to moderate and range from 6-11 miles (6 hours) along farm tracks, dirt roads and minor country roads. Short transfers are included so you can cover more ground and discover the best of these stunning regions on foot.

Tour Style:

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


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

This trip is suitable for:

First Timers

Ideal if you have an interest in:

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

Activity Level & Terrain

Grade & Terrain

This tour is graded easy to moderate with six days of walking and a maximum distance of 11 miles. Daily walks average around 6-11 miles (4-6 hours) along rolling terrain as you walk to-and-from hilltop towns.

Most of the route follows farm tracks and dirt trails, while on some days you will be walking along minor country roads with minimal traffic.

You should be in decent physical shape and comfortable walking every day to fully enjoy the walking on this tour.



While the route is not waymarked (with the exception of some sections), navigating is easy using the Macs Adventure Navigation App.

Your daily walks will be mapped in the app with GPX tracks, including route notes and turn-by-turn directions. All of these resources are available to download for offline use. More information is outlined within your detailed information pack, in addition to 24/7 telephone support from Macs Adventure should you require assistance.



Included in this trip are 9 nights in hand-selected accommodations to ensure that you enjoy every minute of your stay while in Tuscany and Umbria.

We regularly use the following properties but may accommodate you elsewhere if these are unavailable. 

Single Rooms & Solo Walkers

This trips is based on two people sharing a room. If you’d like separate rooms, a single supplement is required.

If you would like to request a twin room (same room with two separate beds), please notify us at the time of booking so we can request this option.

This trip is also available to solo walkers (a solo supplement is required).


Breakfast is included each morning and consists of a traditional European style breakfast ranging from coffee, tea, yogurt, granola, seasonal fruit, meat, cheese and baked goods. In most cases, a hot dish (eggs and pancakes) will be served a la carte or can be ordered off a menu

Two dinners are included during your stay at the more remote La Corte del Poggio country inn to ensure a special experience and the best of Italian cuisine.

Lunches and all other dinners are not included in this trip, so you are free to choose from nearby available options. We recommend finding cafés or restaurants located in the towns or along the walking route, or you can purchase snacks and a picnic lunch to bring along with you. Further details can be found within your information pack and route notes.

  • 9 Nights accommodation in B&B accommodation and 3-4* hotels
  • 9 Breakfasts
  • 2 Dinners at La Corte del Poggio
  • Wine Tasting
  • Private transfer from Montepulciano Stazione to Montepulciano (Day 2)
  • Private transfers to starting and ending points per the itinerary (Day’s 3-8)
  • Luggage transfers (Day's 4, 5, 6 and 8)
  • Turn-by-turn route notes
  • Detailed information pack
  • 24/7 Telephone Support
  • Flights
  • Travel to Siena (arrival)
  • Travel from Florence (onward travel)
  • Train from Siena to Montepulciano Stazione (Day 2)
  • Train from Perugia to Florence (Day 9)
  • Taste of Perugia Guided Tour
  • Cooking Class
  • Travel insurance
  • Lunches, drinks, snacks and all other dinners
  • Personal equipment
  • Private transfer directly from Siena to Montepulciano (Day 2)
  • Private transfer directly from Perugia to Florence (Day 9)
  • Taste of Siena Guided Tour (Day 2)
  • Taste of Perugia Guided Tour (Day 8)
  • Cooking Class (Day 6)
  • Additional nights before, during or after the trip

When To Go

When to Go?

The springs months of April, May and June offer warm sunshine, fewer crowds and pleasant conditions. The autumn months of September and October are also a favorite time of year, boasting cooler weather and a striking landscape made up of a yellow, gold and red pallet.

July and August are also great months to go but can very hot for walking. If booking during these months, we therefore advise you to start your walks very early in the morning to avoid the midday heat.

Getting to the Start

Getting to Siena

By Air & Train:

Pisa and Florence both have airports with flights from international and national destinations.

We recommend flying into Florence and taking a taxi from the airport to the Florence Train Station. Trains to Siena from Florence depart several times per day (approx. 2 hours total, note—some trains are direct while others have a change over in Empoli).

If flying into Pisa, take the tram from the airport to the Pisa Centrale Train Station. Trains to Siena leave from Pisa Centrale Train Station every 30 minutes (approx. 2 hours total, including one change over along the route).

Prices, ticketing and more information can be found within your pre-departure information pack. For additional information, please check the Trenitalia website for updated timetables.

Getting from the End

Getting from Florence

From Florence, buses and taxis connect from the city center to Florence Airport (approx.15-25 min respectively, 20 euros). Or you can take a train to Pisa, Rome or any onward travel destination.

Luggage Transfer

Luggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 50 lbs. 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. 



Our pre-departure information pack has  detailed advice and a packing list on what to bring. This includes warm and cold walking gear, hiking boots, rain gear, day pack and other specifics. 

Travel Insurance

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. 

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 Siena Day 2: Explore Siena & Travel to Montepulciano Day 3: Walk Pienza to Montichiello & Montepulciano 9 miles / 14 km Day 4: Walk to Aquaviva & Transfer to Cortona 6 miles / 10 km Day 5: Walk Ossaia to Tuoro & Transfer to Castel Rigone 10 miles / 16 km Day 6: Transfer to Mongiovino & Walk to Panicale 7 miles / 12 km Day 7: Wine Tasting & Walk from Monte Vibiano 8 miles / 13 km Day 8: Transfer to Monte Tezio & Walk to Perugia 11 miles / 18 km Day 9: Train to Florence & Discover Florence 4 miles / 6 km Day 10: Onward Travel

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