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 five times since 2016, most recently in 2024. 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.
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 will meet everyone at 6:30pm at our apartment for wine and aperitivo before our first group dinner in Spello.
Day Two – Monday
We will travel to Assisi by train and tour Assisi 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 return to Spello for a special lunch in a medieval wine cellar with tastings guided by professional sommeliers and guided olive oil tastings. Lunch includes fresh pasta with shaved black truffles! We’ll conclude our time with our guide with a tour of your home for the week, Spello. You will enjoy free time to rest or explore in the late afternoon with a group dinner to follow.
Day Three – Tuesday
Today we’re off to the beautiful Montefalco and Bevagna area. 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. If time permits we will visit a winery or two following our cooking adventure. We will return to Spello later 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 Spoleto, the city of ancient splendor, via train 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 Four – Thursday
Today we will explore Orvieto and Civita di Bagnoregio. Orvieto is one of the most striking hill towns in central Italy, with a stunning Cathedral, a secret underground world, St. Patrick’s well, and vineyards that produce Orvieto’s famously crisp white wines. Civita, known as the jewel on the hill as well as the town that is dying, must be seen to be truly appreciated. It is pure Italy. They are both uniquely beautiful towns that we are excited to explore together with our guide. We will enjoy lunch and return to Spello in the late afternoon with 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, such as our favorite place for sandwiches that will change your life! 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.
