Tuscany Walking Tours
Super Tuscans & Medieval Wonders
With lush rolling hills, medieval towns and meandering roads keeping it all together, both Tuscany and Umbria are a walker’s idyll. There is something eminently peaceful in wandering through hilltop towns that have stood watch here since the Middle Ages, passing vines tended by generations of winemakers, and savouring traditional cuisine made of the freshest local ingredients. Believe us, once you experience this medieval magic, you’ll never want to leave.
|5 or less||Please contact us|
|6 - 8||From $5,695 per person|
|9 - 11||From $5,195 per person|
|12 or more||From $4,795 per person|
We use premium hotels that are unique expressions of the region. Often they’ve had a previous life as a monastery or a castle, but in every case they offer an exceptionally comfortable stay.
These are stylish 4-star properties that offer a casual and comfortable stay. Often without a 24-hour concierge or room service, they tend to be smaller family-run hotels that are perfect for the region.
“I can’t say I really ‘work out,’ but I’m in good shape and am relatively active.”
“I enjoy a good walk or ride, and feel comfortable while on the move.”
“I get moving at least once a week, and don’t mind a little sweat.”
“I get moving a few times per week and enjoy some exertion.”
“I want to feel invigorated each day and going hard is how I like to do that.”
The right number of like-minded travellers to make new friends.
Your dates. Your group. Our expertly-designed itinerary.
Tailored to your interests, a bespoke travel experience.
Combines the hallmarks of any B&R itinerary (excellent hotels and beautiful routes) with the freedom of pacing each day exactly the way you like.
Our friends on the ground are there to set you up with insider access and expert tips—then disappear when you’d prefer to be on your own.
Our B&R guides are with you throughout, anticipating needs, translating languages, providing advice and—above all—facilitating fun.
6 Days / 5 Nights
Converted from USD based on the latest exchange rate. Final amount and payment will be in USD. Final conversion rate is determined by your bank.
See departure dates for exact pricing Request aDETAILED ITINERARY
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Limited Space / Waitlist
This departure is either sold out or almost fully booked but with deposit we will request additional rooms from our hotels where possible.
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Day by Day
Drive across the Tiber River Valley to arrive in Spello, a walled valley town with ancient Roman roots. Walk into Assisi following the sentiero degli ulivi or “olive tree path,” and stopping to sample some of the local olive oil at a frantoio, or traditional olive oil press.
Take in the magnificent views from the slopes of Monte Subasio in the company of our local hiking guide. Spend the afternoon exploring the hidden alleys of Assisi or at the hotel’s renowned spa before enjoying a night out on the town.
Cross the border into Tuscany to enjoy spectacular views of Lake Trasimeno and walk through the rolling Tuscan countryside. Delight in the delicacies prepared for us during a wine-paired lunch at Avignonesi’s acclaimed winery.
Retrace a Roman road through vineyards and olive groves toward Cortona to spend the afternoon as you please. Tonight enjoy an aperitivo with the hotel owner and her family before moving together to the hotel dining room for dinner.
Drive to the hilltop town famous for its fine wine, Vino Nobile di Montepulciano. After meandering along Montepulciano’s myriad of stone-covered lanes, we’ll embark on our walk through the picture-perfect Val d’Orcia, ending up in the tiny hamlet of Montecchiello for a memorable lunch with breathtaking views over the countryside.
After a farewell breakfast at the hotel, drive to the train station in Chiusi in time to coincide with departures south to Rome. Arrivederci!
Nun Assisi Relais e Spa Museum, Assisi
Nestled in the very heart of Assisi, this hotel seamlessly blends archaic 1stC Roman pillars with state-of-the-art amenities for a luxurious pampering experience. The dining area features cross-vaulted ceilings and décor that also echoes the ages. Each guest room in this reconstructed Saint Catherine’s convent is unique and is a masterful blend of design and history. View hotel website »
Villa di Piazzano, Cortona
This 16thC hunting lodge of a Tuscan cardinal has been beautifully restored and overlooks olive groves and wheat fields. We are warmly welcomed by the Italian-Australian owners, whose garden hosts the perfect spot to take in the sunset after a good day’s adventure. View hotel website »
La Bandita Townhouse, Pienza
La Bandita Townhouse is a boutique hotel tucked inside the historic center of Pienza, a tiny Renaissance village in southern Tuscany. Its 12 guest rooms blend contemporary design with wood beam ceilings, parquet floors and exposed stone walls that are centuries old. A perfect perch to enjoy the local rhythms of life in a Tuscan hilltop town.View hotel website »
We walk on wide, well-maintained trails in Umbria and Tuscany. The average daily distance is 11 km (7 mi.). We have some steep climbs with stunning views and a few steep downhills. The B&R van is always nearby, if you feel you need a lift—though it may not be able to access some portions of the routes.
Walking Sticks &
Included with all walking trips are Leki telescoping walking sticks and custom-made padded hip holsters, which comfortably carry one full half-litre water bottle. And while the walking sticks get “recycled” for use by another B&R traveller, the holsters are yours to keep at trip’s end.
- All hotel accommodation
- All breakfasts, four lunches, four dinners, including wine
- Services of B&R guide(s) and support van
- All special events and private tours
- Use of two lightweight, telescoping walking sticks
- Detailed maps and route suggestions
- Waist pack with water bottle and holder
- All baggage transportation
- All transportation from rendezvous to drop-off
- All gratuities for baggage, porters and hotel service
At Your Service
We take pride in choosing guides who are not only exceptional travelling companions, but who’ll go far beyond the call of duty to ensure an unforgettable experience.
“Meals and tours of the vineyards were great. Loved the hotel selections. Dana did an amazing job - doubly difficult since she was guiding solo!”
— Andrew Resnick,
Tuscany & Umbria Walking 2013
Tuscany & Umbria Walking
Notes from the Road
More stories from our blogREAD THE SLOW ROAD
YOUR TRIP STARTS HERE
Adventure awaits! Click below to take the first step.Request a Detailed Itinerary