Umbria: Culinary Walking Tour – “Absolutely Wonderful”
The Arrival
Traveling together for the first time, two friends and I found Tripsite’s self-guided tour easy to follow. Arriving the night before the official DIY walk, we enjoyed warm hospitality at Hotel Fontebella.
That evening, we wandered around Assisi, spellbound by the breathtaking views of the Umbrian valley and our first taste of local life and local cuisine in the Basilica of St. Clare piazza, where local children played football, families savored gelato, and the water fountain glistened in the orange hues of sunset.
Day 1: A Leisurely Walk in Assisi, a UNESCO World Heritage Site (5-9 Miles)
Early the next morning, Petra, our travel point of contact, reviewed our itinerary with us, set up our mobile apps, answered our questions, and set us off on our first Umbrian walking adventure — a leisurely exploration day of Assisi and its monuments.
Our long, self-paced walk took us to the Basilicas of St. Francis and St. Clare, through enchanting alleyways and twisty-curved streets full of postcard charm, onto a beautiful piazza near the Temple of Minerva, and up to Rocca Maggiore. We found the vibrant green undulating hills with both whispering grass and forested countryside simply sensational.
We stayed at a little cafe outside of Rocco Maggiore, sipping a Limoncello while basking in the beauty of it all. Our spellbinding day ended with reflection on a day rich in Catholic and Franciscan history, stunningly preserved frescoes, the calming hues of ancient stone walls, winding alleys, fairy-tale charm and decorated doors.
After a long day of exploring and walking, our evening brought more delight – gastronomic delight. To this day, months after our trip, we still talk about the exquisite dishes at the Michelin-starred restaurant included in this trip. Words cannot describe; it was divine.
Day 2: Assisi and Its Surroundings (5-9 Miles)
Started with a delicious breakfast at the hotel (included). We walked on the outskirts of Assisi, seeing sites like San Damiano, and spent the rest of the day delighting our tastebuds with the specialities of Assisi: black and white truffles, Pappa al pomodoro, Porchetta, cheeses, and wines from the local trattorias and shops. We had affogatos, and met and shared stories with many shopkeepers and artists.
Assisi was exceptional! Friendly, charming, historical, stunning, and a culinary delight. We found the transitional season to be less crowded and so peaceful.
Day 3: A Walk from Assisi to Spello with an Optional Winery Stop (11.4 Miles and Then Some)
Our morning departure from Assisi was filled with excitement. It started off smoothly, following the app, wandering through olive groves and up into smaller outskirt towns; yet there were times when we became incredibly lost. We thought we were following the written instructions in the app, following the little dot, only to look at Google Maps and see that we had strayed or that the walking path was not where it should be.
After adding a few miles and using Google maps, we found our way back on track to the Sportoletti winery. Petra was on-call to let them know we were running late, and they agreed to stay. We met Matteo, one of the winery owners, who gave us a private tour and tasting of wines, olive oils, and meats that were out of this world.
From the winery and onto Spello – our legs became jello, yet they were energized at the sight of another charming hillside medieval town waiting for our arrival. Once we arrived at our hotel, Spello La Bagista, it was gorgeous. We enjoyed a lovely time in their Venetian-inspired spa; then another walking adventure into town to find a bite to eat.
Spello was equally heart-entrapping as Assisi, yet its offerings were so very different.
Day 4: Spello to Collepino (11-13 Miles)
This was a highlight for sure. My friends and I thought Spello was fantastic, but our walk to Copellino took us through olive groves, forested areas, small-town pathways, and along an ancient aqueduct, with stunning views of the valley, Spello, and Monte Subasio National Park. It was so scenic and so peaceful.
Once in Copellino, we met an Italian man who had resided there his whole life in this very small medieval town. He showed us the view from his garden. His English was not well-versed, and my Italian was equally lacking. He pulled out his dictionary and I, my Google translator, and we learned about his life, his being well over his 90s, and he gifted me this little car – my favorite, most precious item I brought back from Italy.
On this day, we were to walk about 9 miles, but we did walk about 11-13. The long downward slope back into Spello deserves some very sturdy and comfy shoes – it can feel steep and is very gravel-based.
After a fulfilling day of walking and exploring, we were treated to an exceptional meal and time to walk and explore in Spello. The meal and the staff at Endoteca were so wonderful – they were the capstone to the beautiful people, area, and its history. It was truly hard to say goodbye to our trip and our experiences. Our time was short, but our experiences will rest in our memories forever—absolutely wonderful.
Day 5: Departure
We had another lovely breakfast at our hotel (again, included), the staff helped us find the train station, and we bid our farewells to Spello and another fantastically organized and memorable Tripsite adventure.
Note: Although the walking days were longer than expected due to app issues, or wandering off the path intentionally, the distances were leisurely and nothing too strenuous. We had rests along the way.
Shelly Beres is an avid traveler who enjoys discovering unique, off-the-beaten-path travel experiences. Having grown up in California, she has a passion for the outdoors, open-water swimming, cycling, hiking, pickeball, and spending time with her family and dogs.

