Italy
Tuscany
Private Trip
Tuscany Self-Guided Walking
This Private trip is Ready-to-Book!

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.

Trip Details

Hotels:
Signature

Signature

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.

Bistro

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.

Level:
Enthusiast

Occasional

“I can’t say I really ‘work out,’ but I’m in good shape and am relatively active.”

Recreational

“I enjoy a good walk or ride, and feel comfortable while on the move.”

Enthusiast

“I get moving at least once a week, and don’t mind a little sweat.”

Avid

“I get moving a few times per week and enjoy some exertion.”

Expert

“I want to feel invigorated each day and going hard how I like to do that.”

Click here for full details on each activity level »

Type:
Private

Small group

The right number of like-minded travellers to make new friends.

Private

Your dates. Your group. Your way—always.

Support:
Self-Guided

Self-Guided

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.

Locally Supported

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.

Guided

Our B&R guides are with you throughout, anticipating needs, translating languages, providing advice and—above all—facilitating fun.

Terontola to Chiusi
6 Days / 5 Nights

Best Time to Visit

  • January
  • February
  • March
  • April
  • May
  • June
  • July
  • August
  • September
  • October
  • November
  • December
per person from:
$2,995 USD
Single supplement: $800
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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.

Hotels

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 »

Activity Level

Enthusiast

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.

Gear

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.

What's Included

  • 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.

Learn more about our guides »

Accolades

“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

Insider’s Guide: Florence Hotels

Much like the Accademia does for David, a slew of well-appointed Florence hotels will make you feel like a masterpiece during your stay.
more »

Insider’s Guide: Things to Do in Florence

Whether you've got a few hours or a full day, there are plenty of things to do in Florence, home to some of the world's greatest pieces of art.
more »

In Deep: Siena

A perfect medieval time capsule, enlightened zoning restrictions have helped preserve the palaces and churches of Siena like nowhere else in Italy.
more »

More stories from our blog

READ THE SLOW ROAD

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