_{This is part 4 in a series. If you’d like to read Part 1: Orvieto, Part 2: Massa & Cinque Terre or Part 3: Montepulciano & Florence, be my guest.}

The Umbrian hill town of Assisi is known as the birthplace of St. Francis, Italian mystic and poet. The town is very medieval in nature and played an interesting role during World War II. It, like much of Italy, was occupied by Nazi Germany, but the Catholic Church started the Assisi Network designed to house Jews in the many cathedrals, monasteries and convents, keeping them safe through the fascist occupation.

Our drive to Assisi from Montepulciano was a very easy hour (thank the gods), but due to our checkout / check-in times, we knew we’d have some time to kill. I found a parking garage on Google Maps with escalators that led to Assisi’s city center, so we decided to spend a few hours exploring the town before checking in to our hotel.

After visiting a few different shops and cathedrals, then buying a few souvenirs, we decided lunch was a must. We spotted a cute taverna where we were served crispy pork paninis cut straight off the pig and a glass of wine for a mere €5 each! We found a great spot across the way in front of a fountain where we enjoyed our tasty treats.

We did some more wandering and people watching since there were many, many people milling about. It was some kind of religious holiday that I regret not looking up, but involved pilgrims from all over the world coming to pay their respects to the famous Catholic Saint Francis. We dodged people along the stone streets and eventually jumped into a patisserie called La Bottega del Patriccere where we picked up lemon, Oreo and pistachio cannoli. We carried our precious cargo with care until we found an unoccupied alley where we could enjoy.

Once we made it back to the car, it was a mere five-minute drive up a small hill to get to our hotel – the luxurious NUN Assisi Relais & SPA Museum. The hotel was once a functioning monastery and our room included a 20-foot-tall, perfectly preserved fresco from the 1600s. This was considered our “splurge” stay of the trip and they definitely let their ostentatious freak flag fly!

The hotel boasts a phenomenal spa experience that includes a series of rooms at various temperatures and humidity levels, a relaxing therapy pool with many in-pool loungers and massagers for anything that could ail you and massage therapy (by appointment). I was mostly excited, however, to hit up the hotel’s restaurant. The front-desk staff set us up with dinner reservations before walking us to the hotel bar where we enjoyed a pair of cocktails as a welcome gift.

Benedikto is a Michelin-recognized restaurant on the grounds of NUN Assisi Relais & SPA Museum with a bright, though romantic, aesthetic and a vantage point high above the humble town of Assisi. There aren’t many times you can say you enjoyed a Michelin dinner while the sun sets behind an actual castle in the distance, but Katie and I can.

Our first night at Benedikto involved the Trust Fall experience: seven courses of no-holds-barred gastronomic creativity, each paired with an appropriate wine. When I read the description, I assumed we would receive a tasting of each wine.

I was wrong.

The experience started with our server bringing us a small basket of bread and a bottle of olive oil. He let us know that Riserva Marfuga Olio Extravergine di Oliva has won many awards and is widely considered the best olive oil in the world. I must admit my pessimism — how good can an olive oil be, anyway? Again, my assumption was wrong. It was the most beautiful olive oil I’ve ever tasted in my life.

What follows are each of the seven courses, the type of wine paired with it and photos of my voluptuous wife as the evening progressed:

Course 1: Risotto Fritters with Prosecco

Course 2: Veal Tartare with Orange Sauce and Orange Wine

Course 3: Chicken Caesar Salad Fritters over Romaine “Sauce” paired with a White Wine

Course 4: Spaghetti in a Light Sauce served with Baby Asparagus and a Lambrusco

Course 5: Spinach Tortellini over White Sauce with a Cabernet-Based Red Wine Blend

Course 6: Sous Vide Lamb Filet with Vegetables and Mashed Potatoes served with a much-heavier Red Wine

Course 7: Brownie Mousse with Pear Ice Cream served with a Sweet Red Wine

Bonus Course: Assorted Biscotti and Sparkling Water

Yes, all seven courses were served with a full serving of wine, so you could say we were having a blast by the time that Brownie Mousse hit the table. What an incredible experience! Thankfully, our hotel room was merely steps from the restaurant. We stumbled back to our room and almost immediately went to sleep.

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Our next morning started with a five-star continental breakfast that included fresh-squeezed blood orange juice, a variety of pastries, cheeses and cured meats, different breads, cereals and yogurts, and my favorite part: fresh honey, literally dripping from an actual comb. Holy shit, what even is this place?

Our day consisted of the spa experience and a very awkward moment for me wearing the skimpiest underwear on the planet but those stories are both inappropriate and outside of the scope of this post.

Fully spa’d up and massaged, Katie and I got dressed and walked across the street to a bar called blaMblá for the day’s aperitivi. Here, we enjoyed a couple rounds of Bellinis paired with Bacon-and-Cheese Polenta, Bean Soup and Falafel. We were also introduced to a large group of drummers who pregamed at blaMblá before hitting the streets of Assisi marching in formation with thunderous energy.

Dinner that night was back at Benedikto and we started with glasses of the Lambrusco we’d enjoyed the previous evening. From the antipasti menu, we split Lamb Meatballs with Fava Bean Puree, then for entrees we enjoyed Veal Ossobuco with Potatoes and Anchovies, and Grilled Guinea Fowl with Onion Soup Reduction. We finished our evening with Prosecco and Almond Cookies served with Rhubarb, Passion Fruit and Mango Pavolva.

Our time in Assisi was short – one day, two nights – but it made a powerful impact on our hearts (and palates!). I think Montepulciano is still the Italian city for which I have the strongest passion, but Assisi has Katie’s heart for sure. Leaving that following day, just like all other “last days” of this trip was bittersweet. We hated to leave such a flawless fairy tale city, but our next stop was Rome.

Let’s do it.