Backroad Tuscany: 7 steps to (Tuscan) Heaven

Backroad Tuscany: 7 steps to (Tuscan) Heaven

A private day tour along dusty Backroad Tuscany lanes and lesser-known routes, far from glossy brochures and selfie sticks. Depart from Montepulciano and head toward artisans’ workshops, forgotten Renaissance frescoes (yes, real ones), and postcard-perfect hamlets like Montefollonico and Castelmuzio — soaking up sweeping views, curious legends, and cinematic landscapes Hollywood keeps falling for.

Lunch is a rustic feast of crostoni and regional treats in a tucked-away spot. Afterward you’ll follow sun-drenched paths through backroad Tuscany and a stretch of the ancient Via Francigena, stop at a biodynamic winery for a behind-the-scenes visit — walking through the cellar, between barrels and steel tanks, hearing how the wines come to life, and tasting rosé and Sangiovese right where they’re made. The day wraps up in a charming thermal village dating back to Roman times, loved by kings and popes across the centuries.

A journey through beauty, stories, and quiet masterpieces — with one foot in history and a glass in hand, surrounded by the people who keep these places alive

Map of the Backroads Tuscany tour
From 125,00
Trip Enquiry
Trasportation : Included Guide : Included Highlights : Food&Wine, Off the Beaten Accessibility : Accessible Upon Evaluation
BACKROADS-2025

A journey off the beaten path through hilltop hamlets, Renaissance echoes, and cinematic backdrops. From artisans and frescoes to wine and Roman baths — one foot in history, a glass in hand, and Tuscany exactly as it should be: sun-drenched, storied, and beautifully unfiltered.

Photogallery

  • Trip Outline
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Embark on a sunlit odyssey through off‑map Tuscany, where dusty lanes lead from hilltop hamlets to hidden frescoes, biodynamic wineries, artisans’ workshops and centuries‑old thermal springs—seven steps of pure, unfiltered Tuscan magic

Itineraries

Pickup

Time : 9:00 AM

Departure from Montepulciano or Pienza

Morning meet-up and departure aboard the agency vehicle. Direction: countryside, non-touristy edition.

Step 1

Where hands shape tradition

Visit to a traditional artisan studio where clay becomes art (and, sometimes, tableware). Quick intro to local craft techniques and maybe a bit of dust.

Step 2

A terrace above silence

Next, we stroll through a little-known village perched on a ridge, where time clearly took a break. Perfectly restored stone houses, a tiny square, and a terrace that feels like someone’s living room — with one of the most surprising views in the area.

Step 3

Movie Sets & Renaissance Frescoes

Remember The English Patient? Few know it was filmed almost entirely here, inside this ancient monastery that still hosts the Renaissance frescoes visible in the film

Step 4

Lunch, off the map

Time for a proper bite. Rustic lunch with local crostoni, pecorino and cured meats — the kind of food that doesn’t need translating. Served in a quiet, incredible place deep in the countryside, surrounded by olive trees and vineyards, reachable only via an unpaved road. Peaceful, authentic, and delightfully off the radar.

Step 5

Pilgrims, Fortresses and Silent Hills

We drive along a scenic stretch of the Via Francigena, the historic pilgrimage route leading to Rome and, beyond that, to the Holy Land. The road winds through open countryside, with views over rolling hills and ancient castles, and passes beneath a tiny fortified village that once stood guard over this strategic path. A landscape shaped by centuries of footsteps, still alive with stories.

Step 6

Cellar Visit & Wine Tasting

Visit a family-run biodynamic cellar where the winery’s own team leads guests through cool underground vaults to reveal organic winemaking secrets. A guided tasting flight of crisp rosé and robust Sangiovese on a sunlit terrace wraps up the experience

Step 7

A Steaming Pool Instead of a Square

We make our way to a tiny village unlike any other: no central square, just a large steaming pool that’s been bubbling since Roman times. Once a resting spot for popes and pilgrims, today it’s a peaceful corner where history flows — quite literally — from underground. We’ll explore the ancient stone alleys and visit a local herbalist’s shop that feels like stepping into another era, full of natural remedies and age-old wisdom.

Drop-off

Return to starting point

  • Tour leader/local guide for the full experience
  • Typical lunch with crostoni, local cold cuts and cheese, one glass of wine or beer, and water
  • Visits to the sites and villages mentioned in the program
  • Visit to a vineyard and winery with tastings included
  • Vehicle available for all transfers during the day
  • Pick up and drop off in Pienza or Montepulciano
  • Extra drinks, snacks, food or personal purchases
  • Travel insurance (recommended, but totally up to you)
  • Tips 
  • Anything not specifically mentioned in the “Trip includes” section
Group size Price per person Total
Solo traveller €330 €330
2 people €198 €396
3 to 6 people €125 From €375
Business Name: Tuscan Experiences by Federica Zammarchi
Registered Address: Case Sparse Querciole Primo, 8 – 53023 Castiglione d’Orcia (SI), Italy
VAT Number: 01574000525
Chamber of Commerce (REA): REA: 221926 – CCIAA Arezzo-Siena
Electronic Invoicing Code (SDI): USAL8PV
Certified Email (PEC): federica@pec.federicazammarchi.net
Agency Director: Federica Zammarchi (licensed at both regional and national level)
Contact Email: customercare@tuscanexperiences.com
Phone / WhatsApp: +39 379 2349338
Website: tuscanexperiences.com

Insurance & Guarantee Details

Civil Liability Insurance
Policy name: Filo Diretto Errecì
Policy number: 203925172

Travel Guarantee Fund
Policy name: Filo Diretto Protection
Policy number: 203925169
Compliant with Article 50 of the Italian Tourism Code

Insurance Provider
Nobis Compagnia di Assicurazioni S.p.A.
Legal headquarters: Via Lanzo 29 – 10071 Borgaro Torinese (TO), Italy
General management: Viale Gian Bartolomeo Colleoni 21 – 20864 Agrate Brianza (MB), Italy
Phone: +39 039 9890001
Website: www.nobis.it
Email: assicurazioni@nobis.it
PEC: nobisassicurazioni@pec.it

Terms and conditions apply—please ensure you’ve read them carefully before proceeding with your booking.