Small Group
Tuscany & Umbria Walking
From the Golden Land to the Green Heart
6 Days, 5 Nights
Maximum Group Size
16
Activity Level:
B&R Activity Levels
Priced per person from
$8,695 USD
Single Supplement: $2,500 USD
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Carbon Neutral Trip
Walk your way through Tuscany and Umbria, where every trail feels like a love letter to slowing down. Trace ancient paths through Montepulciano and Val d’Orcia, bake crostata with our friend Agnieska, and wander olive groves that roll on forever. With castle stays, Renaissance towns, and a thousand golden horizons, this is Italy at its most soul-soothing.
Unlock access as the only tour group at Reschio Estate, one of the most exclusive properties in Italy.
Preview the itinerary
No two trips are ever the same, but this will give you a taste of what your journey will be like.
Day 1
Our adventure begins just outside of Pienza, where we’ll begin walking through the UNESO-protected Val D’Orcia. Wander through hills of wheat crested with cypress groves, eventually reaching a beautiful Tuscan farm for lunch. This evening, we’ll gather for cocktails and dinners and toast to the beginning of our lovely week.
Activity:
11 km (7 mi.) warm-up walk through the Val d’Orcia
Optional walk | 4 km (2 mi.)
Day 2
Our day begins in the town of Montepulciano, where we’ll pass Medieval architecture etched into the hills, sunny vineyards and fields of wheat. We’ll pause for lunch in the charming village of Monticchiello before continuing to the hotel. This evening, we’ll head to Pienza for a guided walking tour.
Activity:
13 km (8 mi.) walk from Montepulciano to Casa Newton via Monticchiello
Day 3
Follow the trail to the Celle di San Francesco, a hermitage where St. Francis is said to have written his last will and testament. Continue walking through olive groves to Cortona, where we’ll explore the town for lunch. Tonight, we’ll enjoy a fabulous dinner overlooking the town’s main piazza.
Activity:
7 km (4 mi.) to Cortona via Le Celle Hermitage
Optional walk | 2 km (1 mi.)
Day 4
Our route takes us into the neighbouring Umbria, Italy’s “green heart,” where we’ll pass pastures of sheep, cows and hillsides blanketed in wildflowers. Stop to meet our friends Agnieska and Francesco for a crostata lesson and a breezy garden lunch. Then we’re off to Reschio, an old castle and our home for the next two nights for a delicious dinner.
Activity:
9 km (5 mi.) walk through the Umbrian countryside
Day 5
Cross the valley floor flanked by fields of tobacco and wildflowers to the neighbouring hillside of Mount Murlo. Enjoy an intimate lunch of seasonal ingredients before continuing back to the hotel for a relaxing afternoon at the spa or lounging poolside. Tonight, we’ll toast to a magical week in Tuscany and Umbria.
Activity:
6 km (4 mi.) walk up Monte Murlo for lunch
Optional walk | 6 km (4 mi.)
Day 6
After one final breakfast in the castle, we’ll say arrivederci and drive you to Florence for onward travels.
Rendezvous
Airport City: Rome
Trip Start: Westin Excelsior Hotel Florence
Time: 8:30am
Farewell
Airport City: Rome
Trip End: Santa Maria Novella train station
Time: 12:00pm
* Itineraries are subject to change. Please confirm exact Trip Start and Trip End locations upon booking.
Featured stays
Casa Newton
Location: Tuscany, Italy
Monastero Di Cortona
Location: Cortona, Italy
Hotel Castello di Reschio
Location: Umbria, Italy
Dates & availability
Dates
Price
per person, double occupancy
Join
Join a group of up to 16 like-minded travellers.
Privatize
8+ people
Pricing depends on group size
Detailed Itinerary
Uniquely tailored for each date
Can't find your dates?
Get in touch to craft a Bespoke itinerary or request an additional date to Privatize.
What's included
Accommodation & dining
All breakfasts, lunches and dinners as indicated on the itinerary.
All accommodation as indicated on the itinerary.
Thoughtfully selected local wines, beers, cocktails or non-alcoholic beverages with all meals.
Active essentials
Use of two lightweight, telescoping walking sticks and a backpack.
A reusable B&R water bottle.
Detailed GPS routes available via RideWithGPS.
Guided services & gratuities
Services of B&R guide(s).
All special events, private tours, guest experts and entrance fees.
All gratuities for baggage, porters and hotel services.
Transportation & logistics
Transportation from pick up to drop off.
Baggage transportation.
Van support where trails permit.
What's Not Included: International flights, travel protection, gratuity for your B&R guides.
This trip is carbon neutral. Learn more about our Sustainability commitment.
Experience Designer
Good to know
Terrain
Tuscany and Umbria offer diverse terrain, including asphalt, dirt roads and cobblestone paths with some up and downhills. We recommend familiarity with walking in these conditions.
Driving
Due to the nature of this trip, transfers are required to and from the walks on most days.
Packing
To comfortably walk through Tuscany and Umbria, we recommend packing hiking boots or sneakers with a good grip.
Why choose a Small Group trip?
An Effortless Journey
Our expert Experience Designers are perfectionists, using first-hand knowledge of routes, restaurants and hotels to create an unforgettable experience. This means all the planning is taken care of for you. All you need to do is enjoy.
Active Exploration
From emerging destinations to iconic sights, B&R trips show you the world in a new way on our expertly developed cycling, walking and hiking routes. Travelling through historic villages and romantic vineyards and up to striking viewpoints, our routes offer a variety of challenges for every activity level.
Friends for Life
Your fellow travellers are as passionate and curious about the world as you are, which means the conversations and laughs will be as free flowing as your drink of choice. Don't be surprised if your group starts planning a reunion before the trip is done.
Room for Surprises
We love a plan, but we adore a spontaneous moment even more. Whether it’s an impromptu al fresco meal or a moon-lit musical performance, our advice is to expect the unexpected.
Speak to an Expert