Our Italy adventure was based in Milan, where pizza was Dylan’s main priority and music was mine. We got lucky—Pearl Jam was playing at San Siro Stadium, and it turned into one of the most unforgettable concerts we’ve ever seen. In between, we took day trips to Monaco (lunch at Port Hercule), Lucerne (a train ride up Mount Pilatus), Venice (wandering canals and Murano), and Modena (home of Ferrari and incredible food). Italy gave us a mix of history, food, and music that shaped how we’d travel going forward.
This was the trip where our style started to take shape. We weren’t just sightseeing anymore—we were learning how we liked to travel: small hotels, local advice, loose plans, and a willingness to just figure things out when shit went sideways. And on this trip? It did.
🇮🇹 Milan as Our Base
We stayed in Milan for about two weeks and used it as our launchpad. The highlight—for me—was Pearl Jam at San Siro Stadium. Nothing like hearing “Alive” in a stadium full of Italians screaming along with you.
We also made time for some of Milan’s heavy-hitters:
The Last Supper – You need to book ahead, but it was worth it. The Duomo – We climbed it. So many stairs. Worth it. WWII Museum – History lesson tucked into our food tour.
And speaking of food…
🍕 The Food Was the Star
This trip was all about eating—and eating well. Pizza, pasta, gelato, repeat. Every place we stayed, we’d ask locals for their favorite spots, and we skipped anything with a menu full of pictures (that rule was starting to set in).
I always had Dylan order for himself. It’s part of the training—get comfortable with menus you don’t understand. Ask questions. Be okay with being awkward.
One of our best stories came from that: Dylan wanted fries on the side with his pizza. But something got lost in translation… and the pizza showed up with fries ON TOP. Like, baked into the cheese. Still one of our favorite meals.
🚆 Day Trips That Didn’t Go According to Plan (and That’s Fine)
We took some wild day trips on this one:
Monaco: We had lunch at Port Hercule, living bougie for a day. One of those spots where you look around and think, “How did we end up here?” Lucerne, Switzerland: We rode the steepest cog train in the world to the top of Mt. Pilatus—incredible views, chilly air, and a lot of “wow.” The ride back? I booked the wrong train and didn’t realize it until we were already moving. We had to figure out new connections on the fly and somehow made it back to Milan. Travel lesson: have a plan, but be ready to pivot. Venice: No itinerary. Just vibes. We got off the train and wandered through the canals. A local told us to skip the tourist gondola ride and hop on a vaporetto instead—Venice’s water bus. We ended up on Murano Island, way less crowded, great gelato for Dylan and wine for me. No regrets. Modena: Quick stop to see the Ferrari Museum. Not a full-day thing, but totally worth it if you’re a car nerd or just want to see something shiny and red go fast.
🧳 How Our Travel Style Started to Shift
This was the trip where I realized:
I don’t like big hotels—I’d rather stay in a small hotel or hostel with character Tourist restaurants are fine, but local recommendations are always better I love having a plan, but I love ditching the plan even more The less we scheduled, the more we discovered
This trip had it all—music, mishaps, incredible food, and those small, in-between moments where you just get it: travel isn’t about checking boxes. It’s about being open to whatever the day throws at you.
Next stop: Peru—with lifelong friends, big mountains, and a totally different kind of adventure.
Thanks for reading. Wherever we may roam… we eat well, roll with it, and always learn something new.
Wherever We May Roam 