Stroll through the bustling hilltown of Cortona soaking up beauty as old as the Middle Ages. Follow a seamless route through the region—less climbing on buses, more up-to-your-neck immersion.

Gather the brood for an outdoor cooking-lesson (post paddle-boating and medieval flag throwing, of course). Your kids will crash early, which is fine by you…you still have a prize-winning Brunello to polish off.

Follow meandering roads on routes with little or no traffic, so you can have Tuscany all to your self. Welcome to La Dolce Vita.

Get the team together to spin across the Val di Chiana countryside stopping for a lingering lunch at a hilltop vineyard. Later, make some tough decisions: a tasting of Chianti or Brunello? (The answer is both.)

Amble through medieval streets learning the secrets of Italian craftspeople in Oltrarno, a bustling neighbourhood filled with artisans’ workshops. On the docket? Jewelry and leather making; marbled paper and stone mosaics.

A former farmhouse stationed in the rolling Tuscan countryside, L'Olmo once served as a stop for pilgrims hiking along the Via Francigena on their way to Rome. With sweeping views overlooking the Tuscan countryside, this cozy escape features romantic suites, a panoramic heated pool. and an impressive wine cellar. View hotel website »

A simply stunning estate overlooking a quiet corner of Tuscany’s Montalcino area, the beautifully restored village is comprised of 23 suites, two restaurants, an infi nity edge swimming pool, spa and fitness centre. The stylish touch of Massimo Ferragamo and his wife Chiara is apparent in all aspects of the design and layout of the property, ensuring an elegant yet authentically Tuscan experience. View hotel's website >>

Located at the heart of Cortona's historic centre in a converted monastery, this hotel combines the city's immense charm with fresh, contemporary design. Rooms feature elegant interiors and the unique spa is situated in the building's ancient Roman cistern, of which you can still see the brick vaults! View hotel website »