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Radda in Chianti, Province of Siena, Italy for a Base to explore Tuscany and to enjoy local Food & Wine

After a brief stay in Rome, we set out for a scenic drive along the west coast to Grossetto, where we turned inland and navigated the narrow, windy roads into Tuscany.  Our first stop was Pitigliano, which emerged dramatically from a tufa ridge and presented itself to us as we rounded a corner – what an incredible sight to behold it was!  After a great stop for lunch with incredible views of the valley below, we continued onwards with a brief photo stop of neighbouring Sorano, before continuing on to Chianti.

Using Il Borgo di Vescine as a home-base, we explored the Chianti Region of Tuscany as well as Florence.  Borgo means medieval village that has been converted to a small hotel or relais.  With just 28 rooms, it is an intimate property oozing charm and character and run by a spectacular staff who treated us like family from the moment we arrived until our tearful departure.  We enjoyed a fantastic cooking class with chef Hadrian, and Marko, and actually learned some great tips and a trip to Castelvecchi, one of the oldest wineries in the region.  A day trip to Radda in Chianti, about 10 minutes from the borgo was a lovely place to wander for an afternoon.  Not too touristy, but with enough shops, restaurants and a great gelateria to enjoy.     We spent a full and busy day seeing the major sights of Florence including the Accademia where we were enchanted by the majesty of David, the majestic Uffizi Gallery and a walking tour of the main sights such as the Duomo, leather market and Bridge of Sighs.    We booked and EatWith experience on the outskirts of Florence and enjoyed an organic meal with Joanne and her family at their rustic home with an amazing sunset view and great conversation.  Our final adventure was a day trip to San Gimignano.  While it is a popular tourist spot, the crowds were well dispersed and we still managed to find a few quiet spots to enjoy.  A great spot for shopping – we snagged a gorgeous hand-made, one-of-a-kind olive wood charcuterie board, a beautiful painting by an expat Canadian artist who found love and settled in Tuscany and creates stunning images of the countryside, and some fun eggs made of Alabaster for the kids. 

Leaving Tuscany for the Amalfi Coast, we stopped in Orvieto, an incredible hilltop town with Etruscan origins.  Set 1000 feet above the valley floor, Orvieto is known primarily for the extravagant facade of its cathedral and for the 16th-century engineering marvel of St. Peters Well.  It’s a great spot for lunch and a wander and has inviting cobblestone streets full of interesting shops.

In five days, we barely scratched the surface of Chianti, let alone Tuscany

Insider Tip

Take the scenic route to Chianti from Rome and stop in Pitigliano for lunch. It’s one of the most incredible hilltop towns in Italy and not well known!

Where I stayed / started

Il Borgo di Vescine


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