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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

$6,395 USD

Prices May Vary For Groups Larger Than Two

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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 sipping wine at La Bandita Townhouse. Skip the schedule, linger in the piazza, and live like the Tuscans do—indulgently, emphatically and gloriously free of stress.

UNESCO Site

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.


Historic Sites

Discover Tuscany's rich history, from the legendary Sanguineto to the enchanting medieval town of Montepulciano.


Exclusive Access

Meet our trusted local friends and guides, who greet you with warm hospitality and provide exclusive access to the very heart of the region.

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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 B&R host Carlo for a short introduction to Pienza, the Renaissance hill town envisioned by Pope Pius II. Stretch your legs along the Path of Art and Soul, where contemporary sculptures frame sweeping views of the Val d’Orcia. Or follow a scenic loop past the quiet church of Pieve di Corsignano and along the cinematic countryside roads featured in The Gladiator.

Activity:

Guided tour of Pienza

Optional | 3.9 km (2.4 mi.) 

Optional | 7 km (5 mi.)

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Day 2

Set out from your hotel for a scenic walk through the Val d’Orcia, heading toward the hilltop hamlet of Monticchiello—a perfect stop for coffee. Continue through vineyards and wheat fields to the Renaissance temple of San Biagio, then climb into Montepulciano, where lively piazzas and wine bars make an ideal lunch stop.

Tonight, head to a nearby restaurant or pizzeria for a lively local dinner.

 

Activity:

Morning walk | 12.7km (7.8 mi.)

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Day 3

Begin with a short transfer into the Val di Chiana, then set out on a peaceful walk through fields of poppies and sunflowers toward the hermitage of Le Celle, where St. Francis once lived.

Continue through olive groves to the hill town of Cortona, where artisan shops and cafés make a perfect lunch stop. For sweeping views, opt for a walk up to the Medici-era Girifalco Fortress. Finish the day savouring Cortona’s culinary delights.

Activity:

Morning walk | 7 km (4.3 mi.)

Optional | 2 km (1.2 mi.)

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Day 4

This morning, our local guide will take you on a walk through Cortona, uncovering its history while taking in views over the valley and Lake Trasimeno.

After lunch in town, follow a gentle downhill walk through the Val d’Esse, passing tobacco fields and quiet country lanes before arriving at Villa di Piazzano along a classic cypress-lined drive.

Activity:

Morning walk | 11.8 km (7.3 mi.)

Guided walking tour of Cortona

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Day 5

Set out from the hotel on a rewarding walk up to a ridge overlooking Lake Trasimeno, where sweeping views await. Continue through the tiny hamlet of Sanguineto before reaching Tuoro on the lakeshore, an ideal spot for a relaxed lunch.

Tonight, celebrate your final evening. Salute!

Activity:

Morning walk | 13.6 km (8.45 mi.) 

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Day 6

Linger over breakfast before a private car takes you to Camucia-Cortona train station.

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Get in touch

We always love to chat travel. Let’s see what trip is right for you.

Featured stays

Itinerary

La Bandita Townhouse

Location: Pienza, Italy

Itinerary

Monastero Di Cortona

Location: Cortona, Italy

Itinerary

Villa di Piazzano

Location: Cortona, 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.

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This trip is carbon neutral. Learn more about our Sustainability commitment.

Experience Designer

Good to know

Terrain
Terrain

Some walks have challenging uphills and uneven terrain. We recommend familiarity with hiking in these conditions.

Getting there/home
Getting there/home

We recommend connecting from Florence or Rome via train or private transfer from Florence, available upon request.

Packing
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
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.

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Discover further

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6 Days, 5 Nights | April – June, September – October