Villa le Maschere | Florence, Italy — The Humble Pineapple Club

The basic idea of a hotel is simple: give the guest a bed, and put that bed (and, I guess by extension, that guest) in a safe place. Over the centuries, this simple tenet has blossomed into a multibillion-dollar industry, giving the weary adventurer and savvy traveler alike a place to rest, relax, and recharge. But what is truly amazing in the modern hotel world is how varied and unique the modern place of lodging can really be.

the exquisite Medieval-chic lobby of the Villa le Maschere

To continue my European Adventure, I will find myself caught up in the countryside of Toscana. I awoke rested from my fantastic sleep at the Lungarno Continentale and spent my morning touring the city, stopping by the Uffizi and the Cattedrale di Santa Maria del Fiore, and doing my very best to navigate the crowds streaming up and down Ponte Vecchio. Soon, though, it was time to leave the beautiful little city. I’m sure I’ll be back (I made sure I rubbed the boar’s nose), and after grabbing my bags, I took a quick, pleasant car ride from downtown Florence through the Tuscan countryside. It was stunning. The weather had been on point, and today was no exception.

The reason I am starting quite a bit before actually being in the hotel is intentional. Just as some great movies are more enjoyable when you read the book, or how some paintings are made even more beautiful when you learn of the struggles the artist went through to produce – well, for some hotels, it’s the exact same situation.

And for the Villa le Maschere, well, you really, really need the whole picture.

This hotel is, in a word, astonishing. Before even reaching it, one must drive through the quaint village of Barberino, about 30 minutes north of Florence. The hills roll by, and the air is crisp and cool. The area is famous for its milk and beef, and the people that live in the village are kind and friendly. The little road climbs up from Barberino, passing first by a small castle (yes, a real one), then finally arriving at the gravel drive leading up to the Villa. By this time, it is the early afternoon for me, and the sunlight played off the lightyellow walls of the ancient home.

Astonishing.

The grounds are simple, yet tasteful and inviting, and the lobby and guest areas follow suit. Walking in, my jaw continued to drop. This was a genuine Italian villa, dating from the latter 1500s, home to royalty, haven for popes, and site of many famous parties and events. The lobby and surrounding guest areas were simply stunning. I was given a property tour by the hotel manager, Luiggi, and the moment we stepped into the first room and he began to share the history, I knew this place was one of a kind.

Villa le Maschere, prior to renovations — Villa le Maschere, prior to renovations

The Villa, aside from hosting all those aforementioned guests and events, fell into total disrepair in the 1900s. I didn’t fully understand how bad it was until he showed pictures from before the restoration, but suffice to say, the place was uninhabitable. They spent 5 years painstakingly restoring every detail of the property, under the guidance of the Florentine Government.

The process was a true labor of love. Each room I saw was marked and named by former famous guests, researched and vetted. Tile floors were restored and replicated to exact detail. Grotesque ceiling art was hand-painted. Original paintings and frescos were discovered and preserved. Nothing was carelessly done.

The results are evident in every room, and on almost every surface. This property regularly took my breath away. My room had a view of the grounds of the villa, and the mountains beyond, and I could open my windows wide to the crisp Tuscan air.

The guest areas are also tastefully done. The lobby is large and inviting, with many plus couches to lounge on. The front desk is set off to the side of the front entrance, but the front desk staff were attentive and engaging. The bar is well-stocked, and my bartended Lorenzo entertained me for hours with stories of his time in America, and his well-made amaretto sours. There is plenty of space to sit, although I had the place to myself for most of the evening.

The dining room was gorgeous, and dinner was on-point, with friendly, helpful staff and delicious fare. The back, outside area of the property has walk-able sections, and is used commonly for groups and events. They also restored the original chapel on the grounds, and it along with several other rooms provide ample meeting space.

Seeing places like Villa le Maschere give me a little bit of hope for the future. Knowing that someone saw beauty in the ruins of this centuries-old home instead of demolishing it makes me hope that it will inspire more people to do the same. Modern, sleek hotels are fantastic, too, don’t get me wrong: I work in a modern, edgy, trend-setting property, and I love it.

But should you ever get the opportunity to visit Villa le Maschere and take the time to wander it’s warren of halls and stairs, you’ll understand that not all luxury comes from stainless steel and seamless electronics. Somewhere on this Tuscan hillside, you may just catch a glimpse of an older, deeper-rooted form of luxury, Italian style.