Small group
Tuscany & Umbria Walking

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.

Trip Details



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 how I like to do that.”

Click here for full details on each activity level »

Small group

Small group

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.

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.


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

Spoleto to Florence
6 Days / 5 Nights
per person from:
$4,995 USD
Single supplement: 600
See departure dates for exact pricing Request aDETAILED ITINERARY


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.



Have a group already?

Make it a private trip by taking over one of our dates, or we can request a fresh one. Prices are sliding scale to suit the number of travellers.
Request your PRIVATE DATE

Day by Day

Take a guided walking tour of the historic center of Spoleto before heading to Monteluco for an introduction to the local cuisine. Tonight we’ll dine al fresco with Spoleto’s magnificent duomo as our backdrop.

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 and enjoy a lunch of the local torta al testo. Spend the afternoon in 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. We are welcomed into the home of a charming local family for lunch, where we’ll sample Mamma Dina’s unforgettable homemade pasta.

Retrace a Roman road through vineyards and olive groves toward Cortona to spend the day as you please. Indulge in an exclusive final night celebratory dinner in a famed winery which opens its doors just for us.

After a farewell breakfast at the hotel, drive to the train station in Florence in time to coincide with departures south to Rome. Arrivederci!


Palazzo Leti, Spoleto

Meticulously restored to its original antiquated beauty, the Palazzo Leti offers an unforgettable hotel experience. Consisting of 12 rustic-yet-elegant rooms and located in the heart of equally historic Spoleto, guests will marvel at the architecture, noble luxury and sweeping views (including the sacred Monteluco Mountain) that this luxurious property offers. View hotel website »

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 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 »

Activity Level


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 &
Hip Holsters

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.

What's Included

  • 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.

Learn more about our guides »


“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

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 »

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