Go Castle to Castle in Italy
The regions of Tuscany, Umbria, and Marche are famous for their ancient hill towns, but what few people know is that many of the castles atop those hills now function as hotels. Hopping among them is the perfect way to tour the region. It's even better if you do it on that most iconic of Italian vehicles, the Vespa. Start in Assisi, which is located in the middle of the three regions. Do parts of the following loop, or commit to the whole thing and really experience the slow-paced charms of the Italian countryside.
Day One: In Assisi, we picked up a classic Vespa PX, consolidated our essentials into a daypack, tied it to the scooter's rack, and set off. We were soon hugging the shore of Lake Trasimeno, shaded by willows and poplars. After a detour to Siena, we arrived at Castello di Leonina, a 13th-century fortress and the summer home of Pope Alexander VII. The 21 rooms have been renovated since his day; a room with breakfast starts at $120.
Day Two: We broke up the 45-mile journey with lunch in Montalcino, where we sampled its famous Brunellos. Then we rode south to the monolithic Castello di Potentino. Dating to the 11th century, it is now run by a British family who resurrected the vineyard. Co-owner Charlotte Horton persuaded us that due to low sulfites, their organic wine doesn't cause headaches. We tested the theory late into the night — and woke up hangover-free. Rooms cost $160 and include breakfast.
Day Three: Our longest travel day (160 miles) took us over Tuscan mountain roads before descending to the olive orchards of Umbria and up into the Marche region. We arrived at Castel di Luco in time for a six-course prix fixe dinner ($38) and then retired to renovated 15th-century craftsman quarters with original travertine walls and wood-beamed ceilings ($165).
Day Four: Crossing back into Umbria, we went north to Castello di Petroia, a building complex dating from 1072 and surrounded by sheer stone walls. The watchtower is about 60 feet high, with one cramped bedroom and a spectacular rooftop terrace ($228 in high season). At breakfast we met hikers retracing the path used by Saint Francis. We took notes for our next trip, then fired up the Vespa for the 20-mile farewell spin back to Assisi.
How to Do It: At Umbria Scooter Rental in Assisi, a Vespa goes for $55 a day or $260 a week. For the less adventurous, guided Vespa tours are offered starting at $110 a day.
Keep in Mind: Touring by Vespa is slower, noisier, and harder on the body than traveling by car, so plan to ride just 40 or so miles a day. And beware of local drivers, who have a penchant for tailgating while talking animatedly on their phones.