My wife and I traveled to Italy April 24-May 1 for a bucket-list trip. We wanted to split our short time between Tuscany and Umbria, stay in small towns, and explore the small towns and villages of the area.
We decided to stay in Castellina in Chianti and use that as our home base in Tuscany and use the Assisi area for our home base in Umbria. Since we flew in and out of Florence, Castellina worked really well for Tuscany since it was roughly one hour from the airport, and Tuscany was the first half of our trip.
While in the Chianti region of Tuscany, we explored Radda, Gaiole, Castle Barole, Monteriggioni, and the Greve area. We really liked Castellina, Radda, Gaiole, and Castle Barole; Monteriggioni had too many tourists for our tastes. We stayed at Hotel Colle Etrusco Salivolpi, which is right on the edge of Castellina and easy walking distance to the shops and restaurants of the town. The lodging was nice, we were treated well, and the ladies who worked the desk were very knowledgeable about the area, made suggestions of where to visit and where to eat, and were multilingual.
In the Assisi area, we hit the jackpot by staying six miles (10 kilometers) north of Assisi at Le Ginestre Bed and Breakfast. The inn sits atop a ridge-line overlooking a beautiful valley, and I could have sat on the patio or at the pool and stared at the valley for hours--it's gorgeous! The room was immaculate, and the fixtures in the bathroom were new. The breakfasts each morning were superb, and Sylvia Gold, the proprietor (who communicated extensively with us prior to our leaving for Italy and who is multilingual), will fix sandwiches and snacks for her guests for a small fee. We ate sandwiches one evening with a bottle of wine we bought at the inn, and enjoyed the evening sitting on the patio. Sylvia also suggested that we eat at Livia's (the restaurant at the B&B at the bottom of the hill 800 meters or so from Le Ginestre). For 30 euros, we had a fabulous eight-course meal, that included a bottle of wine and a glass of liqueur.
Back to our explorations: We obviously toured Assisi, and we also went to Spello and Montefalco to the south. We took the very narrow and winding road north from Le Ginestre to Gubbio and Monteone; even though the road wasn't great for the first 20 or so miles as we left Le Ginestre, the scenery was fabulous. Our favorites in the portion of Umbria we explored were Montefalco and Monteone. There were very few tourists at Monteone, and it is a really nice walled town with good views.
On our way from Castellina to the Assisi-area, we dropped south of Lago Trasimeno to go to Panicale, a small walled town that is wonderfully preserved. There were probably only a dozen other tourists in town, so we enjoyed that. Because it is up on a hill, the views of the countryside are wonderful! We ate at Albergo Ristorante Masolino and sat on their balcony. The view was spectacular! I think Panicale is one of the hidden treasures of all of Italy.
The weather was perfect while we were there, with highs in the upper 70s (F) and lows in the low 50s (F).
For only having 5-6 days to explore, this trip was perfect for us to explore the small towns, villages, and countryside of the Chianti region of Tuscany and a portion of Umbria.