Hilltowns & Castles

The area around Villa Vianci is a dense mosaic of walled hilltowns, castles, abbeys, and craft towns, each with a distinct character, and all within easy reach for day trips.

From Villa Vianci, a series of genuinely rewarding hilltowns and fortified villages can be reached with ease as comfortable day trips. These are not “checklist” stops, but places where Tuscany reads clearly in stone and landscape: medieval skylines, civic piazzas, Romanesque churches, Etruscan traces, and small centres where craft, wine, and history still feel embedded in everyday life. Below you’ll find nine curated itineraries, each designed as a clear, walkable visit with a practical route, the essential things to see, and one nearby stop to deepen the day without turning it into a long drive.

Turn this day trip into a true Tuscan stay. Villa Vianci is a private 18th-century villa between Florence & Siena, available only as an exclusive rental for up to 14 guests.

Why it works so well

Central base for day trips: easy access to Florence, Siena, San Gimignano, Monteriggioni, Chianti, Val d’Orcia — and many more Tuscany highlights, without changing accommodation
Made for groups: generous shared spaces, privacy, and A/C in all bedrooms
Unwind at home: peaceful grounds and a private swimming pool — perfect after a busy day out (or a slow day in)
Optional experiences: private chef dinners, pasta making class, and Chianti wine tours

Enquire for your dates on our website: best available online rate, direct contact with the hosts, and help planning your stay.

Share this Post 👉

Related Posts

Request availability

Fill out the form below and we will contact you as soon as possible