Itinerary – Umbria October 19-25, 2025
Our inaugural tour will be to the Umbria region of Italy. By chance we discovered Spello, a small hilltop village in Umbria, the green heart of Italy. We have visited countless times since 2016, most recently in June 2025. Not only is Spello a magical village but the area around it is also very special. We have developed a treasured friendship with a local resident of Spello who has helped us experience the local Umbrian life. Our hope is to share this experience with you. To learn more about Le Bon Chaperon please click here.
To secure your place in Umbria please click here to register. ONLY 2 SPOTS REMAINING!
Please note, breakfast will be on your own each morning and we will meet at the square for our group departure for the days activities. Each day we plan to return mid to late afternoon so you will have free time to rest or explore Spello as you please. You will likely find us at one of our favorite local spots! Dinner will be in Spello each evening. For being a small village, it is simply incredible the number of truly outstanding restaurants! Daily itinerary is subject to change based on availability.
Day One – Sunday, Arrival to Spello
Ciao! We will greet you at the Termini station in Rome and chaperon you to Spello via train arriving in Spello in the early afternoon. We will show you to your apartment and allow you time to settle in after your arrival. We kick off the trip at our favorite wine bar for a light food and wine tasting that evening.
Day Two – Monday
Today we will visit Spoleto, the city of ancient splendor, and tour with our local friend, Stefania. Spoleto’s cobblestone streets are lined with medieval walls over 800 years old. The city is bursting with history at every turn and impressive, grand architecture. We will enjoy lunch in Spoleto at a beautiful, Michelin recommended restaurant known for its unique culinary creations. We will return to Spello late afternoon and enjoy dinner together that evening.
Day Three – Tuesday
Today we’re off to the beautiful Montefalco and Bevagna area. This will be our day to explore Montefalco in the morning and enjoy lunch and tasting at a vineyard in Bevagna. We had the good fortune to be there for their first vineyard dinner of the season. It was spectacular and we cannot wait to take you here! It is owned by a young man and his sister. They are truly wonderful, very hospitable people. We’ll return to Spello in the afternoon and enjoy dinner together that evening.
Day Four – Wednesday
Today is market day in Spello. You’re welcome to explore the market in the morning before we travel to Assisi and tour the Basilica with our local guide who is a longtime resident of Assisi with a vast knowledge of the area. Assisi is the home of St. Francis of Assisi and truly a beautiful place. We will enjoy lunch in Assisi before heading to Eremo, the woods where St. Francis lived. You will enjoy free time to rest or explore in the late afternoon with a group dinner to follow in a medieval wine cellar with wine tastings guided by professional sommeliers and fresh pasta with shaved black truffles!
Day Four – Thursday
We will spend the day attending a unique cooking class at an Umbrian farmhouse nestled amid ancient olive orchards on a scenic hill above Bevagna. Our host ensures an unforgettable culinary experience! We will enjoy a morning of hands on cooking, mid morning aperitivo, followed by an afternoon savoring the fruits of our labor for lunch. Their vision is to create an experience where you work together and prepare a meal just like an Umbrian family would do together. Their concept is “not to look, but to work” so it will be all hands on deck and a memorable day. We will return to Spello later in the afternoon and enjoy dinner together that evening.
Day Five – Friday
It’s our final day together and your free day to do as you please! Some ideas include walking the ancient Roman aqueduct, olive picking with our local friends, shopping (Spello has lovely stores for linen clothes, olive wood, pottery, and kitchen linens), re-visiting Assisi, Spoleto or even Foligno or simply stay in Spello and live like a local. Lunch will be on your own today and we can help you with suggestions. We will enjoy a farewell dinner at one of our favorite Spello restaurants.
Saturday – Departure
Our week has come to a close with memories to last a lifetime. We will accompany you to the Spello train station for your morning departure back to Rome or wherever your next destination may be. Arrivederci!
To secure your place in Umbria please click here to register.
