Who: Kelly Engemoen of Lakewood
Where: Castello di Montegualandro, overlooking Cortona on the border of Tuscany and Umbria
Best meal: Dinner at La Tufa, a Cortona restaurant with an outside terrace overlooking the countryside. The food, wine and sunset were outstanding.
Best deal: Visits to nearby hill towns. The Tuscan and Umbrian hillsides are filled with beautiful old towns, usually surrounded by a protective wall, and are easily accessible by car. Wine-tasting is free in many places. We would buy fresh bread and meat at a store and then enjoy picnic lunches in between sightseeing, shopping and absorbing the culture.
Best time to go: When we went in early June, the temperatures were pleasant, the sky was clear, and the number of tourists was moderate. We would guess crowds are not a problem during much of the year, although July and August would likely be quite warm.
Best travel tip: We would highly recommend a stay at the Castello di Montegualandro. This well-restored castle dates to at least 800 A.D. – four former servant quarters that have been beautifully transformed into apartments complete with small kitchens. No phone or TV was a plus for us! While much of our two-week tour through Italy included busy days in must-see cities, this stop was filled with beautiful and relaxing days in an idyllic setting.



