Every experience in our Private Trip Collection offers the hallmarks B&R's known for with the flexibility of going with your own group and on your own schedule. Simply pick your dates, pack your bags, and go.
Tuscany Walking Tour
Structured Independence in B&R Style
Combining the hallmarks of any B&R itinerary—excellent hotels and beautiful walking routes—we provide the freedom of pacing each day just the way you like. We arrange some can’t miss meals and events, transfer your bags and equip you with all the information you’ll need to craft the trip you desire. A morning browsing the shops, or an extra trail loop; take-away pizza or a gourmet lunch; a walking tour of historic Cortona or relaxing in a piazza—the choices are yours on this Tuscany walking tour.
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
Best Time to Visit
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Based on 4 ppl double occupancy Request your date for exact pricing Request aDETAILED ITINERARY REQUEST your DATE
await the challenge.
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Day by Day
Explore southeastern Tuscany's olive groves and cypress trees, before settling in for dinner at the historic Villa di Piazzano.
Take a jaunt into neighbouring Umbria for a walk overlooking the shores of Lake Trasimeno, with a lunch stop in picturesque Tuoro.
Meander into Cortona's bustling historic centre, hear its history from colourful local guide Giovanni and then explore its myriad of boutiques, cafes and restaurants.
Cross the Chiana Valley to Renaissance Pienza with its shops featuring the local speciality pecorino cheese and views of Monte Amiata. Evening wine tasting of regional vintages in Montepulciano.
Walk a vineyard loop through Montefollonico with its spectacular views over the Valdi Chiana before enjoying a final night in town.
Linger over breakfast before a private car takes you to the train station in Chiusi.
Villa di Piazzano, Cortona
This 15thC manor house, once belonging to a Tuscan cardinal, is located in the countryside just outside the town of Cortona, on the border between Tuscany and Umbria. It has been beautifully restored and overlooks endless olive groves and wheat fields. Guests are warmly welcomed by the Italian-Australian owners, whose garden is the perfect spot to take in the sunset. View hotel website »
Villa Marsili, Cortona
Villa Marsili is situated inside the walls of Cortona and dates back as far as the 15thC, where the site housed the church Madonna degli Alemanni. Later in the 1700s, the site held the villa that now has become Villa Marsili. With its refined lounges, and finely furnished, frescoed bedrooms, this villa’s cozy atmosphere offers one of the town's most elegant residences. View hotel website »
Il Tosco, Montepulciano
This new, four-room property offers ample, traditional-style decor with gorgeous bathrooms. Its best feature is the location in the historic centre, which allows quick access to meal options and walking, or to an oasis when you want to step out of the fray. View hotel website »
For the most part, you’ll walk on gently rolling terrain, although there is the occasional steep climb or descent to take on. As the terrain can be rocky, footwear with good ankle support is essential. On average, we walk 10-13 km daily, with longer options available on some days.
- All hotel accommodation
- All breakfasts and one dinner, including wine
- All baggage transportation
- 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
- A private walking tour of Cortona
- A private tasting of regional wines
- Transportation to drop-off
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.
“We loved everything, especially the food recommendations. Overall, the trip was fantastic. Can't wait to do another self-guided trip.”
— Steve & Stephanie Korn,
Tuscany Self-Guided Walking 2011
Tuscany Self-Guided Walking
Notes from the Road
More stories from our blogREAD THE SLOW ROAD
6 Days / 5 Nights
Price from: $4,495 USD
6 Days / 5 Nights
Price from: $6,795 USD
6 Days / 5 Nights
Price from: $2,995 USD
YOUR TRIP STARTS HERE
Adventure awaits! Click below to take the first step.Request a Detailed Itinerary