9 minute read

Italian Villa Trip 2024

tldr: We spent 24 hours traveling to 90° excessive heat to get away from 100° excessive heat. Housed (in a posh 2-story stone Villa), fed (from personal chefs + served by staff), and driven (by hired van services) around the Tuscany region of Italy removed the fundamental aspects of life in an effort to spawn this thing called relaxation and rest. Perhaps not ironically, the rest was irksome, and I felt lacking of meaning, purpose, and identity. However, the people, the conversations, and the generosity of the hosts carried the day on this trip.

The Concept

The concept is something I have always wanted to do. Invite your 10 closest friends and their partners and vacation for a week together. Anywhere really. The goal is to be with people you love and have memorable, shared, human experiences away from the typical work/life balance. And Meg’s best friend growing up made this happen!

As part of her honeymoon, she and her husband invited their closest friends to a week-long stay at a rented Villa in the Tuscany region of Italy. Technically, there were 2 Villas needed to house all the guests and family attending.

The Villa we stayed in was a 2-story stone building that had rooms for about 6-8 couples, a kitchen, a dinning room, a parlor, a sitting room, a pool, and more. It had a terra-cotta roof with shingles, a 9-foot high stone wall encircling the compound, and a pebble driveway protected by electronic access automatic steel gates. The hedges along the tops of the walls were squarely trimmed with just the occasional over-achieving stem popping up. There are 50-foot tall evergreen trees that look like giant popsicles making one wonder if they were manicured that way or natural. Sprinkled around them are tall, broad sycamores and magnolias that have to be over 100 years old.

Picture of the back of the Villa where the pool is located.

At the end of the pool and the once functioning fountain are large stone and brick walls decorated with statue-like faces menacingly starring at you. The tops of these walls are crumbling, indicating the authenticity and age of the once elaborate, but now antique adornments of the grounds. Once can sense this is the sort of place where new and perfect lines are associated with gauche, while aged and crumbling provides a sense of authenticity and class.

It is not like the really fancy hotels in the city that have a doorman and you feel like you need to justify your worthiness to enter. Here, I feel like can enter the Villa freely as long as I don’t touch or break anything. That door handle is probably older than I am, and I don’t think you can pick up a replacement at whatever the Italian equivalent of Lowes is (Lowesano?).

The Schlep

Waiting for the 3-hour train ride to Penn Station (achem…Moynihan Train Station now) in New York was hot and sticky both indoors and on the track. The train was delayed 15 minutes in Fredericksburg, VA which was perpetuated to New Carrollton. Next, we took the A C E subway to Brooklyn which was rather easy and quick. Good job New York.

Skipping over the wedding day, we then took the subway continuing to Broadway Junction where we changed to the A J line to JFK International Airport. Side note: Brooklyn Junction was like being in a different country. I saw a 10-year-old boy selling candy bars from train to train and carts with women cutting fresh fruit to sell at the station. At the JFK stop, another Air Train ticket gets you to the airport.

We boarded a somewhat spacious and comfortable 787 Dreamliner airplane for the 6-hour flight to London, Gatwick. I enjoyed the in-flight movies which I am not used to on domestic flights, but my ass did not enjoy the seats and my ears did not enjoy the earbuds for that long. Sitting for more than an hour or so is not in my DNA.

I’ll skip over the 8-hour layover in Gatwick; lucky for you. The EasyJet plane was anything but. A 30-minute late plane caused ripple effects by pushing us out of the tarmac queue which pushed us into a storm delay. Our 2:20pm departure didn’t depart until about 5:20pm. With the time delta, we got to the Villa (via a taxi from Pisa) at about 8:30pm which was 2:30pm Eastern Time or about 24 hours after getting on our Brooklyn subway.

The Food

Nearly every meal is professionally prepared by what appears to be 2 chefs. The spreads are amazing and the thoughtfulness apparent. Off to the side of each buffet is a gluten-free card behind a plate of gluten-free options. Even more adorable is that for every lunch and dinner, they set aside a plate for me labeled vegan. On it, they always have some plant-based nuggets and a side of hummus.

Picture of the dedicated vegan plate.

For dinner, they started putting cubes of tofu and veggie patties. I told the organizer I didn’t need special treatment. I brought pea protein and part of being vegan is being able to scrounge for items I will eat. Nevertheless, it is a pleasant surprise, and Meg likes finding my custom vegan plate off to the side.

Asked if I miss the Italian cheese and meats, I probably do for that instant the savory fats would touch my tongue. Sitting by the pool enjoying both the sun and the breeze, after I have had a full belly of proteins and grains and veggies, I can’t say I would know the difference. I think that is the difference between vegans/non-drinkers and people who eat all food and drinks. One wants the short-term pleasure, and the other is willing to forgo short-term pleasure for longer-term null differences or possible advantages.

The Trips

The bride planned two day-trips to nearby cities (Lucca and Florence) complete with van service from the Villa. Others created their own trips to Pisa or wine tasting. Within the day trips were English guided tours. We took advantage of the Lucca guided tour which was helpful, but we did Florence on our own. Both days were full sun, over 90°F, and humid. The mornings were bearable, but after lunch was a drag. Towards the end, I had to focus just to walk straight and drink fluids.

a. Picture of a Church in Lucca against a bell tower with the sun beating down., b. Picture of the Duomo through the city street.

Some people in the group really like the history and arts. They nerded out on Puccini in Lucca or da Vinci in Florence. For the 100th anniversary of Puccini’s death, the town is doing a nightly concert this summer which was well attended by Meg and others in our group. I am not a fan of museums or concerts. I am good for a painting or two; maybe a song or two. But after that, I am ready for the next thing.

It is nice seeing new things in new cities. If I could sum up the trips, they are one step above sitting around doing nothing. However, asked if I want to go again the next day, the novelty ran out and I would rather sit and do nothing.

The People

The people make the difference, really in all aspects of life, but also on vacations. The people on this trip were knowledgeable, eclectic, sociable, friendly, and diverse in age. We didn’t bring our own kids, but some families with young ones did. The one thing people didn’t bring were their pets and I am grateful.

My favorite part about conversing with all the guests are the breakfasts and dinner conversations. The breakfast tables are smaller, requiring intimate groups of 3-6 before starting a new table. Also, there is a common understanding that people aren’t caffeinated when they first sit down. A grunt is an acceptable response at this point while a question about politics is a faux pas. However, the conversation is allowed to build staring with a “how did you sleep?” to “do you have plans today?” eventually leading to stories about pets or home-life. But only after the mandatory 30 minutes of small talk as the coffee takes effect.

It is also nice to see the slow parade of morning birds, to normies, to night-owls make their repeatable jaunt to the breakfast patio. The brain chemicals are strong and consistent in this species.

Picture of the breakfast patio as viewed by the early birds.

Dinner is a different animal. First, everyone arrives near the same time, near the same level of alertness (depends on how many aperol spritzes they had at the pool), at large group tables. The attire is a step above pool lounging, but not coat and tie stuff. The placement of nice dinning ware with chilled bottles of flat and sparkling water set the mood. Alcohol is not the dominant feature and is only consumed by about half the guests.

Picture of the dinner patio set up nicely.

As it turned out, we sat near different groups of people each night. Gone were the insecurities of youth with their cliques. People were interested in the others whether knowing them for years or just meeting them. There were acedemics, teachers, charitable organizational leaders, therapists, technology adjacent experts, life coaches, doctors, lawyers, and some fields too niche to get into here (you know who you are). The conversations flowed into dessert while the outdoor lights turned on and the young ones were shuttled off to bed. Each couple would then say their goodnights as they departed in a similar pattern to the breakfast arrival.

The Reflection

This was a more than generous gift and a once-in-a-lifetime experience the bride and groom gave to their family and friends. For the traveler, it was most ideal; for the non-traveler, it was an ordeal. As a wise man I met at the wedding put it, “Why are you traveling to Italy? What is there that is so special?”. I whole wholeheartedly agree. If there was an easier way to get people from all across America to meet up for a meandering breakfast each day, that would be amazing. Then, at the end of the day, if those same folks came together after a full and meaningful day at work to share a dinner, what could be better? But in the modern world with everyone spread out, not knowing or liking our neighbors, the comfort of solitude, this sort of togetherness is more the exception than the rule.

As much as I disliked the schlep, disliked being in foreign countries, disliked visiting historic cities, and disliked even more sitting around the pool with nothing to do but read or dip into the water, the trip solidified the importance of people and conversation. Returning to home/work brought back the sense of pride and meaning one gets from achieving, providing, learning, and doing. Instead of looking forward to another trip to Italy, I will rewrite the goal as “Next Year in Maryland!”

Here is a gallery of some of the photos of Villa. 2024 Italy Trip Gallery

Matt relaxing at the pool on a lawn chair.