Self-Guided
Tuscany Self-Guided Walking
Stroll through Tuscan splendour
6 Days, 5 Nights
Activity Level:
B&R Activity Levels
Best Time To Go
April – June, September – October
Priced per person from
$5,295 USD
Prices May Vary For Groups Larger Than Two
Carbon Neutral Trip
In Tuscany, the only thing even remotely rigid is the pasta al dente. Wander at your own pace from Cortona’s cobbled streets with our storytelling friend to wine tastings at La Bandita Townhouse. Skip the schedule, linger in the piazza, and live like the Tuscans do—indulgently, emphatically and gloriously free of stress.
Stroll through the sweeping open fields of the UNESCO-listed Val d’Orcia, a lush green valley dotted with charming hilltop towns and ancient cypress groves.
Discover Tuscany's rich history, from the legendary Sanguineto to the enchanting medieval town of Montepulciano.
Meet our trusted local friends and guides, who greet you with warm hospitality and provide exclusive access to the very heart of the region.
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
Meet Carlo, your local host before exploring the Val di Chiana, which borders Umbria and offers stunning views of Lago Trasimeno, a perfect introduction to the region. Walk up the cypress-tree lined driveway to reach your first hotel before enjoying your first taste of Tuscan cuisine.
Activity:
9 km (6 mi.) moderate walk from Terontola to Piazzano | Elevation gain: 260 m (853 ft.)
Day 2
Your walk begins with a slow but challenging climb to the ridge overlooking Lago Trasimeno, with rewarding views of beautiful vistas. Arrive in the town for Tuoro for lunch, then continue on a trail that will lead you back to the hotel. Tonight, head to a nearby restaurant or pizzeria for a lively local dinner.
Activity:
17 km (11 mi.) loop to Tuoro from Piazzano with several rolling hills | Elevation gain: 586 m (1,922 ft.)
Day 3
Today’s journey takes you on foot through the serene Val d’Esse, past tobacco plantations and towards the hilltop town of Cortona. Arriving by midday, you’ll have time to explore its charming streets before joining a local expert for a tour of the town’s history and hidden stories. Finish the day savouring Cortona’s culinary delights.
Activity:
12 km (7 mi.) morning walk from Piazzano to Cortona | Elevation gain: 312 m (1,023 ft.)
Day 4
After exploring the medieval hilltop town of Montepulciano, set off to Renaissance Pienza where you'll be lured in by pecorino cheese and views of Monte Amiata. Pause for lunch in the postcard-perfect village of Monticchiello, then meet your guide for a walking tour of Pienza.
Activity:
13 km (8 mi.) moderate walking with several good climbs from Montepulciano to Pienza | Elevation gain: 389 m (1,276 ft.)
Day 5
Wander through the fields of Val d'Orcia, with its rich green valley, charming hilltop towns and ancient olive groves. Back in Pienza, opt for the Path of the Art and Soul, relaxing among contemporary sculptures along the way, before enjoying one final dinner.
Activity:
7 km (5 mi.) loop around Pienza with gorgeous scenery and several good climbs | Elevation gain: 203 m (666 ft.)
Day 6
Linger over breakfast before a private car takes you to the train station in Chiusi.
* Itineraries are subject to change. Please confirm exact Trip Start and Trip End locations upon booking.
Featured stays
Villa di Piazzano
Location: Cortona, Italy
Monastero Di Cortona
Location: Cortona, Italy
La Bandita Townhouse
Location: Pienza, Italy
What's included
Accommodation & dining
All accommodation as indicated on the itinerary.
All breakfasts, lunches and dinners as indicated on the itinerary.
Restaurant suggestions along the way.
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
Private walking tour of Cortona.
Private tasting of regional wines.
All special events and private tours as indicated on the itinerary.
Transportation & logistics
All baggage transportation.
Transportation from pick up to drop off.
What's Not Included: International flights, travel protection, gratuity for your guides.
This trip is carbon neutral. Learn more about our Sustainability commitment.
Experience Designer
Good to know
Terrain
Some walks have challenging uphills and uneven terrain. We recommend familiarity with hiking in these conditions.
Getting there/home
We recommend connecting from Florence or Rome via train or private transfer from Florence, available upon request.
Packing
Tuscany can have variable weather throughout the day in October. We recommend packing a Gore-Tex raincoat to stay comfortable and dry.
Pre and Post trip
If you have extra time, consider extending your trip with a visit to Florence or Rome.
Why choose a Self-Guided trip?
Total Freedom, Tailored to You
With a self-guided trip, you are the master of your own adventure. Every route, hotel, and dining experience is meticulously planned by our expert team, leaving you free to explore at your own pace. Follow our guidance or take that unmarked path that catches your eye—it's your call.
Set Your Own Pace
Whether you're an early bird who loves watching the sunrise or a traveller who prefers leisurely mornings, self-guided trips let you design each day to your rhythm. No strict schedules or group timetables—just the perfect balance of adventure and relaxation, as you like it.
Support Behind the Scenes
Though you're on your own, you're never truly alone. Our local experts are just a call away, ready to offer support if needed. From roadside assistance to restaurant recommendations, we're there to ensure your journey is seamless and stress-free.
A Private Escape
Craving a solo adventure or a getaway with your closest companions? A self-guided trip offers the privacy to create lasting memories with your travel partner(s), free from distractions. The world is yours to explore, with no group to keep up with or slow you down.
Speak to an Expert