Everywhere we stayed, dined, drank, and shopped (!!) in Milan
Recapping everywhere we checked out in Milan during the Olympics
Happy Olympic Closing Ceremony Sunday!
Did you catch that nail-biter gold medal win for the US men’s hockey team today?? Full body chills. Between the men’s team snagging their first gold since 1980, the women’s hockey team also claiming an OT win against Canada, and Alysa Liu’s poetic performance, these last few days of the Games feel like they’re following a movie script.
Before we dive into all of our Milano fun, I need to take a beat to look back at last Sunday’s letter. If you haven’t had a chance to read it just yet, I’m shamelessly going to redirect your energy to what was a very special “Between the Lines” edition with Julia & Thomas Berolzheimer. I’m still not over her thoughtful answers and what an honor it was to feature a creator whom I’ve admired for so long.
Before we dive in, a quick note on what this recap is—and in equal measure, what this Mini Milan Guide isn’t.
I’ve written plenty of destination guides for my paid subscribers in my years of writing TSS (including Nantucket, Paris, Mallorca, and more), each meticulously crafted after multiple visits to a destination—once I’ve wandered enough neighborhoods, tested plenty of tables, and stayed in enough hotels to feel like I can offer holistic recommendations.
And while it wasn’t my first visit to Milan, I hadn’t been back since I was seventeen, so it may as well have been. With the Games as our primary focus, our time at leisure was limited. So, think of this as my curated edit of Milan, shaped by Olympic energy, tables recommended by trusted locals, all anchored by two very chic hotel stays. It’s not exhaustive, but a roundup of exactly what I feel is worth your time. As always, I’m reserving these tidbits gleaned from my visit for paid subscribers.
On that note, let’s dive in. The city was absolutely abuzz with energy during our time on the ground—from brushing up with Martha Stewart at the original Prada store to spending a perfect 60-degree Sunday having lunch at a local friend’s favorite trattoria, we were riding a major high the entire trip.
For fear of being too name dropp-y, to further paint a picture of just how vibrant Milan felt this past week, beyond Ms. Stewart, Tieghan of Half Baked Harvest-fame struck up conversation with us while having coffee at Principe di Savoia, Regé-Jean Page (Bridgerton) was checking out of The Carlton as we were leaving the hotel for the day, and Seth Meyers was checking into our Emirates flight at the same time as us at Malpensa yesterday. Needless to say…VIBES WERE HIGH.
There are so many sensational hotels in Milan, even more so this year, with a great deal of development happening in the city. We did a split stay since we broke up our time with FORESTIS (more on this Dolomites oasis in a future letter) at two very different properties!
Hotel Principe di Savoia: We were fortunate to start our trip in a well-appointed suite at the Principe. I’m a huge fan of the Dorchester Collection properties, and this stay was no different. Their team always nails it from a service perspective—they made us feel SO special, even going so far as to make our Valentine’s Day arrival extra sweet with red balloons anchored by photos of us! The club sandwich we got from room service on arrival revived me, and the sensational daily breakfast spread was also a treat to wake up to each morning. Notably, this hotel is turning 100 next year, so it’s got some old bones—you’re not coming here for the freshest product in town, but instead a property that has a soul.
The Carlton, A Rocco Forte Hotel: On the complete opposite end of the spectrum, on our final two nights, we stayed at the newest property in Milan. Opened in November 2025, The Carlton is an elegant 71-room oasis. As with all other Rocco Forte properties, this family-owned gem was designed by Olga Polizzi and is bursting with color. The subterranean Irene Forte spa (her products are incredible!) and fitness center stood out as feeling especially fresh. Don’t miss ordering the carbonara omelet at breakfast. Especially love the location, with a back entrance directly onto Via della Spiga, a spectacular shopping street.
Nuova Arena (Piazza Lega Lombarda, 5, 20154 Milano MI, Italy): This spot was the aforementioned Sunday lunch, and I can’t overstate how much we loved it. Probably my favorite meal of the trip, not just because we were the only table speaking English, but because the ambiance, service, and food were everything you want from a no-frills Milanese trattoria. Will be 10000% be back.
Trattoria Milanese (Via Santa Marta, 11, 20123 Milano MI, Italy): Located in the narrow streets of the historic city center, this has been a meeting point for posh Milanese for decades. Here, we opted for prosciutto and melon, the classic veal Milanese, sauteed veggies, saffron risotto, and tiramisu. No notes.
