Family Plan

When I first decided this adventure would be starting in Europe, I knew that I would finally be visiting Italy. I also knew I wanted to give it as much time and attention as I could. After informing my family of my plans, my sister Liz was the first person to say they were definitely going to visit me. I immediately knew she meant Italy, long a dream destination for us both. With my three months in Italy decided for late summer through early fall, we set about booking flights, and then she went into planning mode.

As I've made my way around Europe, and with the months flying by, the date of her arrival snuck on me a bit. Nevertheless, I was so excited to spend some quality time with her and her partner Topher.


I left Genova mid-morning, targeting an arrival that would be as close to hers as possible. Our apartment rental was in the Navigli neighborhood, which was exciting since Eli and I only spent a short time exploring back in August.

Upon meeting up at Milano Centrale station, we made our way to the apartment. Being back in Milano, a place I knew very well now, meant navigation was my primary role in the group. As a geography aficionado, I relished this role. It also felt great to be somewhere I could navigate without constantly map-checking.

After a quick rest, we made our way out into the streets of Navigli. We grabbed some Arancini, deep-fried cheesy rice balls, to snack on as we continued on. With a long day of travel behind them, we kept our first evening quite mellow, not straying outside of Navigli. We capped our night with cocktails at a wonderful bar around the corner from our apartment, before retiring early.

The next day was an all-action sort of day. It began with a stop at the Wes Anderson-designed Bar Luce for caffe and breakfast. A quick metro ride had us at Duomo, in the heart of old town, in no time. We had tickets for the Duomo rooftop, but not until 12:30, so we strolled through the Galleria and wandered the streets of old town.

At our assigned time, we ascended to the roof of Duomo for some of the most amazing views of Milano. You can walk around the edges of the cathedral, but the real gem is walking its spine, giving you 360º views of the city. Amazing, even if my acrophobia was in full effect.

With our views indulged, it was time for a bite to eat. We found our way to Bar Bianco, in Parco Sempione, where Eli and I had enjoyed a great lunch the month prior. Refueled, gelato was now on our minds. We were close to one of my favorite spots, and a quick walk through the Brera neighborhood found us at Oggi for the best gelato in town.

Feeling like quite the tour guide now, I lead the group to Cimitero Monumentale. The large, opulent tombs never cease to amaze. It really is quite a destination. Feels like a park but it's definitely a cemetery.

This set us up perfectly for a visit to my favorite destination in all of Milano, Biblioteca degli Alberi, and the beautiful Bosco Verticale. I've been here more than any place on my adventures. As we lounged in the park, I mindlessly picked at the grass. Then I realized I had found my first ever four-leaf clover! I wasn't even looking for one, it just presented itself to me.


The next morning, we hopped a train bound for Rome. As with many of my other train journeys, our departure was delayed. Feeling a bit tired upon arrival, we chilled for a bit, before making our way into the neighborhood to grab some delicious pizzas for dinner.

Morning arrived with a slight drizzle, but not enough to dampen our spirits. So we set out to see the sights, full tourist mode! You name the old thing, and we saw it! Trevi Fountain, Pantheon and Piazza Venezia were all appetizers for the main course … the Colosseum.

The weather cooperated wonderfully. The sun broke out from behind the clouds just enough to bathe the ancient building in its warm glow.

So far Rome was giving me that impersonal “just another big city” vibe that I’ve found in a few other large cities, like Madrid and London. It didn’t feel as ancient as I thought it would and it didn’t have the Italian charm of other cities I’d visited.

Then Rome answered the call. Leaving the Colosseum, our meandering led us into the Testaccio neighborhood, and Piazza Testaccio. I was immediately enthralled by this tiny, unassuming piazza where everyday life was happening. I felt like I was missing something about Rome, with all the touristic locations we had visited that day, and this place was the perfect tonic for that. I love finding the everyday, slice-of-life parts of a city. It connects me to a place and gives me a sense of belonging.

The piazza was alive with the life of Romans. Kids kicking a soccer ball, adults conversing, drinks in hand. And a couple of musicians serenaded everyone. Topher grabbed some Aperol Spritz’s and we joyfully took in the scene. When in Rome …

piazza testaccio

The next day started much like the previous one. Drizzle and grey abounded. And like the day before, we didn’t let that stop us. Having visited most of the big attractions yesterday, we explored the city in my favorite way, by wandering. Rome being Rome, served up plenty of stunning piazzas and vistas along the way.

In the early afternoon, heavier rain moved in. We took refuge in Villa Borghese, the largest public park in Rome. We found a quiet little cafe to have a few Negronis, watch the parakeets and wait out the rain.

With the rains subsiding, we walked around the massive park for quite some time, having some great conversations. Eventually, we found our way to the Spanish Steps. The sun had finally come out, so I took the opportunity to enjoy its warmth. At this point, Topher decided to explore on a scooter, while Liz and I continued on foot. We planned to meet up for cocktails at a hotel bar Liz had wanted to check out.

After a nice dinner in a quiet piazza, we started back towards the apartment. Along the way, we realized we were coming up on the Vatican, so we decide to check it out.

WHOA! Its magnitude and opulence cannot be overstated. It is massive. We were really glad we came to St. Peter’s Square at night, as it was all lit up, making it even more impressive. A perfect way to cap off our time in Rome.


Cinque Terre

Cinque Terre, meaning five towns. A region of the Italian coastline famed for its tiny towns perched on the sea cliffs, and also for its huge crowds of tourists.

We had hoped that by coming in late September that the crowds would have somewhat abated. Thankfully this was the case. While we didn’t have the place to ourselves, we also weren’t fighting for space or waiting in lines at viewpoints or restaurants either. This made for an enjoyable and relaxing few days along the Italian Riviera.

On our first evening, we shared a bottle of wine and took golden-hour photos of Riomaggiore. Topher then got us a table at a cliffside bar to watch sunset proper. We made friends with another traveler and enjoyed our next couple of days with her. Stephanie was solo traveling at the moment, before heading to a wedding in the Tuscan countryside the following week.

Much of our time over the following days were spent relaxing on cliffside rocks, admiring the view. Liz and I had the chance to spend some top-class quality time together. It was so a great to get one-on-one time together as adults, not something we’ve had the chance to do much of over the years.
On the afternoon of our last day, we venture out to see one of the other town, picking Monterossa. Quite different from Rio, it has a large, sandy beach. It’s Main Street ran along the coastline, rather than up the hillside like in Riomaggiore.

Topher braved the chilly weather, and even cooler water to take a quick swim in the Mediterranean, while the rest of us watched on. We decided to stay in Monterossa for dinner and lucked into the most charming spot. Cucina di Miky is the sister restaurant to Michelin-starred Ristorante Miky.

I had two of the best Negronis I’ve ever tasted. The restaurant smokes, then barrel ages the cocktail, giving it a depth and earthiness I’ve not found in another Negroni. Possibly the best cocktails I’ve had on my travels.

Sadly, this brought a close to Topher and Liz’s time in Italy. The next day they would head back to Milano to catch their flights home. And I would make my way down the entire length of Italy to Puglia, where I would be spending the next month in Torre a Mare.

Making friends and having people to share this adventure with is always great. It's hugely positive for my mental and emotional well-being. But having family along for the ride is a whole other level. There is a comfort with family that is almost undetectable, but in retrospect and in the absence of, it's wholly noticeable. Getting the opportunity to feel that comfort, even for just a few days, was revitalizing.

The time spent together was also an opportunity to know my sister in a different way, as an adult and an individual outside our family dynamic. Throughout our chats, we found we had so much in common. Things I’m not sure we would have known if not for having this time together. The hours we spent on the rocks of Riomaggiore are some of my favorite moments of this adventure.

I’m so glad Liz was the first person to say they wanted to find me on this adventure and I can’t wait for her to join me again somewhere else in the world.