Itinerary – Umbria October 18-24, 2026
Thank you for introducing us to Spello. It was truly a magical experience. The relationships you have built are priceless. – Dawn, Umbria 2025
Our second annual 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 and took our inaugural tour with Le Bon Chaperon in October of 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 with this highly curated and personal tour of Umbria. To learn more about Le Bon Chaperon please click here.
Reserve your spot in Umbria today!
Optional Early Arrival – Saturday
You have the option to check-in early to your apartment on Saturday afternoon. There is no additional charge for this extra day! You will be on your own until the group tour begins on Sunday evening. Enjoy wandering the streets of Spello, get lost, and fall in love with this charming village.
Day One – Sunday, Arrival to Spello
Ciao! We will greet you at the train station in Foligno at approximately 2:30pm (time will be finalized once train schedule is available, times can vary slightly) and chaperon you to Spello via private driver arriving in Spello in the early afternoon. If you miss the group transfer you will be responsible for your transportation. 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 regional 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 at a favorite local restaurant.
Day Three – Tuesday
Today we’re off to the beautiful Montefalco and Bevagna area. This will be our day to briefly explore the city of Montefalco in the morning followed by lunch and wine tastings at two beautiful vineyards around Montefalco and Bevagna. These vineyards are spectacular and we cannot wait to share them with you. They are family owned and truly wonderful, hospitable people. Dinner will be on your own this evening in Spello.
Day Four – Wednesday
Today 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’ll start our visit with breakfast together and conversation with our guide, Anne. Lunch will be on your own today so that you can explore Assisi as you wish. Following our time in Assisi we will visit Eremo, the woods where St. Francis lived. It is truly an experience that brings the your time in Assisi full circle. We will enjoy dinner together in Spello that evening.
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. You will leave with all recipes from our class together. 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 simply stay in Spello and live like a local. Lunch will be on your own today. 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, approximately 10am, or wherever your next destination may be. Arrivederci!
Join us in 2026! Reserve your spot in Umbria today!
100% of 2025 Umbria trip participants said the trip met or exceeded their expectations, would travel with Le Bon Chaperon again, and would recommend Le Bon Chaperon trips!
