It all started with a dream.
If you really needed me to, I could spend half a day scrolling up through my text thread with Shaun until I found the message—the one where I told him I loved him, I hope he’d have a great day, and I just had a fantasy of us lazing around together on a boat in Italy. It’s something we do often and out loud: dream back and forth of a daring and luxurious sweetness, visions of future experiences to amplify the sweet life we’re already blessed with.

Catching a ride to Europe
I was walking to Trader Joe’s when he texted me back: a friend had just extended a last-minute invite for us to join him on his trip to Milan. It would be quick, easy, and minimally planned, but based on all of my previous travel experiences with Shaun, I knew it would be maximally enjoyed.
Being and having a partner is quite new to me. I’ve always been a bit of a lone wolf, and I’ve liked it that way. But meeting Shaun felt like finding the other half of my soul, and while I’ve always loved traveling and seeing new places on my own, I’ve found that doing so with a partner in life, love, and creativity is one of the best parts of life I didn’t know I was missing.
With him, I can say yes to anything with no anxiety, stress, or second-guessing. I’ll bring my strong suits (navigating public transportation and being able to sniff out a fantastic restaurant from miles away) and he’ll bring his (speaking shockingly good Italian and making friends everywhere we go); together, every experience is amplified in its perfection, and enjoying beautiful sights, incredible food, and international people-watching is so much better when you have someone next to you to nudge.
A quick and easy “yes” is how we wound up in Milan, armed with adventurous spirits and a few great recommendations from my friend who used to live near the city. Instead of researching ahead of time and packing our five-day itinerary with destinations and obligations, we decided to feel our way through the streets, using my friend’s suggestions as a loose compass for the directions we wanted to wander in.
The Type A’s reading this are sweating, but it’s how we usually prefer to travel, and when it comes to trying to see a city in such a short amount of time, I highly recommend throwing a little caution to the wind and just seeing where it takes you. Chances are, there’s beauty, intrigue, history—or, at the very least, some form of dark comedy—in every direction.

In our case, we had a few line items prepared that we wanted to tackle:
Food
Fashion
Coffee
Cool old churches (and general Gothic-Baroque architecture we were sure to find)
Lago di Como was a loose aspiration, solely based on the fact that: 1. Shaun knew it was near Milan and 2. I had dreamed of us being on a boat together. We also knew we’d be spending half of our last day in Venice to fly home from there, and that instead of trying to plan anything with such a tight window, we’d 100% just be wandering through the canals and bridges.
Two days on foot in Milan
Although we were only there for just over two days, Milan felt like homebase to me. I felt like I became quickly and deeply familiarized with it while I was there; this probably isn’t actually true as there was so much I didn’t get to see, but the fashion areas reminded me so much of New York, I sort of felt like I’d traveled back in time to my internship days at Harper’s Bazaar—minus having to lug twenty pounds of garment bags around on the subway.
I found it easy to navigate and packed with such a rich history: imprints of past visitors and locals that have bled into the fabric of the city throughout the years. I remember feeling that way about New York’s old buildings and sweaty streets when I first moved there, and since Italy has thousands of years on NYC, this was felt even more viscerally.
We used the Duomo as our North Star: it was about a 30-minute walk from our hotel, so every morning, we’d get up, set off in its direction, and then take the rest of our day from there. Steeped in centuries of history and one of the main hot spots for tourists, the Duomo is also right near the fashion areas I was dying to explore, so it made for the perfect starting point for our days in the city.

After just under two days exploring the many windy streets surrounding the Piazza del Duomo, we decided to expand our reach a bit and venture out to Lago di Como.
The best day ever: In Como!
This was my favorite day of the trip. We got up early and I took the lead on navigation, dusting off my MTA cobwebs to guide us through the tunnels of the Milan Metro, heading to Milano Centrale. For me, it was a fun challenge: using my knowledge of public transportation and figuring out how to apply it to an entirely new country. It was half intuitive and half very confusing, but with the aid of kind strangers we encountered on our journey, we found ourselves in Como by noon.

Como was insanely beautiful. There were stunning lake views; gorgeous, colorful homes nestled in the hills above; the mouthwatering scents of fresh food wafting out onto the cobblestone streets; and a shopping scene that was comparable to Milan, but more custom, handmade, and affordable.
If you read my previous post about eating our way through Italy, you’ll know it was Como where we had the best bowls of pasta. The cafe had such a friendly, small-town feel; I could easily picture myself ducking in there with my laptop to write the day away in a corner, accompanied by cup after cup of espresso.
The lake was breathtaking; we found a small pier that allowed us to walk into the center of it, surrounded by placid, blue water, ruffled by nothing more than a few boats and quiet fishermen. The day ended with gelato, some shopping, and catching the train back “home” to Milan. It was perfect.
A half- (and final) day wandering through Venice
We ended our trip in Venice, where we had about eight hours to cram in some exploration before we had to go to bed and get ready to make our way to the airport the next morning. With such a small window, we decided to plan nothing and just walk around.
This was the best way to see Venice in a few short hours: letting the paths and canals unfold us from one part of the city to another as we soaked in the history, the tourism, and the largely-abandoned buildings above. While I preferred Milan (there was a much higher concentration of tourists in Venice, which I didn’t love…although the fact that I was even there means I was part of the problem!), it was cool to see Shaun take in Venice; he fell in love with the history of the city, and I enjoyed watching him take it in.
I guess that’s one of the best parts of traveling with a partner you love: Their joy becomes yours, and what cool experiences you might have cherished on your own are doubled. And joy felt endless on this trip; I was and am still overwhelmed with gratitude, and I can’t wait to go back and explore more.
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