At B&R we make it incredibly easy for you to journey with your friends, family, colleagues or on your own. Create your own 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. Interested in tweaking the itinerary? We can do that too. Ask us for details!
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.
Throughout the day, a knowledgeable local guide provides insider access and expert tips. At night, you can explore and dine on your own.
Our B&R guides are with you throughout, anticipating needs, translating languages, providing advice and—above all—facilitating fun.
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.”
Wander through hilltop towns
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.
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Spoleto to Florence request a DETAILED ITINERARY
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Go with the right number of like-minded travellers to make new friends.
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This departure is either sold out or almost fully booked but with deposit we will request additional rooms from our hotels where possible.
Tuscany & Umbria WalkingBOOK NOW
Your private Tuscany & Umbria Walking trip
FROM (USD) †
|2-5||*Call for details|
|† Double occupancy|
* Trip elements may be adjusted on smaller group sizes.
Have a custom trip designed exactly to your interests. Like a tailor making a bespoke suit, it will fit you perfectly.
Our Bespoke trip designers are a talented bunch who can craft unforgettable experiences for your specific group—and working within your needs and budget.
Get in touch with a Trip Designer to begin planning your perfect vacation.REQUEST A QUOTE
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!
Take in the Tuscan sun.Request a Detailed ItineraryTuscany & Umbria Walking
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 »
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
We never wanted to be the biggest travel company in the world, just the best.
— George Butterfield
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.
“I go on a long walk once a week, and I don’t mind a little sweat.”
Rolling terrain on a variety of surfaces. Most days, one or two steeper climbs to spectacular viewpoints or places of interest.Read more on our Activity Levels
What’s included? Everything you need. Plus everything you’d
want. Plus a few things you never knew you wanted ‘til you got them.
In a word: everything. In ninety words? Signature B&R guides; local experts; unique, unforgettable biking and walking routes; private tours; authentic local cuisine; lessons and demonstrations; local artisanal wines; wine tastings; all victuals and libations; all the endorphins you can handle; new insight; interesting, fun and like-minded travel companions; a feeling of total freedom. In short: an extraordinary, hassle-free journey of discovery.
- All hotel accommodation
- All breakfasts, three 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
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.
Notes from the road, on the B&R blog.
Whoooooa Nelly! The Drama, Majesty and Excitement of Siena’s Palio
In Deep: A Brief History of Montepulciano
In Tuscany, Home is Where the Hospitality Is
Travel Two Ways
In Tuscany, A Resplendent Reward
Insider’s Guide: Florence Hotels
Insider’s Guide: Things to Do in Florence
In Deep: Siena
Rave Reviews: Tuscany
Tuscany Biking: The Tour of a Lifetime
Video: Three Minutes in Tuscany
An Enchanting Encounter at Villa La Foce
A Few Lessons in Family Travel
Dinner with (the Woefully Underdressed, if Impressively Sculpted) David
Vines 101: Chianti Wine
Cuisine 101: An Introduction to the Cuisine of Tuscany
Immersion Kit: What You Need to Know About Tuscany
More Trip Inspiration
And your mind? Totally and utterly blown.
We craft extraordinary experiences, tailor made to meet
your every need, with every stitch of every day crafted
just the way you want it. Learn more about Bespoke