milan - a long weekend
fun ways to spend a few days
Milan is a wonderful city for a long weekend + with so much going on here this month (Winter Olympics, Women’s Fashion Week, my birthday), I thought I’d put together a little guide. Milan can be so spread out, that it’s hard to feel the heartbeat. But there are pockets of life. This guide focuses on hanging out like a local and less on top hits lists. Grouped generally by area* and ease of getting around. A lived in experience of a high-end city.
VENEZIA / TRICOLORE / OTHER?
Grab coffee at Loste (the best macchiato in Milan) on the way to the gorgeous Villa Necchi. Looking into open Palazzo doors is a must, as there are so many cool entryways in this part of town. And make sure to stop and see the flamingos at Villa Invernizzi! It’s a peak through the gate situation, so it won’t take a lot of time but is well worth the walk by.
After pretending to live at the villa for a while, continue that lux life at Terroir. Here you’ll find speciality groceries, a cool curation of products, or get a hit of health with a juice. You can also have a glass of wine and chill on the benches in front if it’s actually nice out. Or maybe it’s proper wine time. If so, Temp is a lovely little wine bar just down the street. Then definitely dinner at Giacomo Bistro. It’s well-known, but for a reason. The interiors are incredible and it’s one of the best meals I’ve had in Milan (and I’ve had a lot). All the other Giacomos are also worth a mention.
VENEZIA (this one I’m sure about!)
Or if you want less fancy and a bit more hip, head to Venezia. Coffee at Orsonero, check out the magazines at Frab’s, maybe get some more film at Film Color. There’s several cute shops in this neighborhood, including one of the city’s best Bivios (designer resale at really reasonable prices). They currently have a gorgeous Loro Piana suit that I wish fit, but alas I’m not a men’s size 48.
Then you’re all set for aperitivo with a wealth of choices. But if you’re only here for a few days, Bar Basso is kind of a necessity. While it’s one of the most-hyped spots, it’s also an institution and actually fun! Embrace the grouchy servers (not literally) and enjoy your giant negroni (the negroni sbagliato was invented here, but they only come in normal sizes…).
TRICOLORE / PORTA VITTORIA / I DON’T KNOW
Another east side hood with some cool spots. The Seed is great to get some work done and have a healthy snack. Or sneak in some yoga at The Garden next door. It’s all about balance, right? Vicolo via Mameli for home goods for sure, including fantastic in-house candles. Rehub is worth checking for affordable second-hand designer. The Etro outlet is nearby.
At this point, you’ll want something more than avocado toast. There are a few great food, great vibes non-Italian restaurant options in the area - Le Presine Volanti, Money in the City, Pizza Stella (I mean ok, it’s pizza. But it’s NY style pizza). For Milanese, which you are here after all, Trattoria Masuelli is a classic. Make a reservation. Eat a giant cotoletta (off menu).
Or head a little south and hit up the wine bars. Vino is small and a bit of a scene but nice wine and proper music. Get there right when they open to get a seat. Enoteca LM (is that the name of this place??) is bigger, more chill and has some great classic wines if you’re over the whole natural wine thing. Being Italy, both of course also have food. So either could be a keep it cozy, one spot night.
PORTA ROMANA / AGAIN NO IDEA
Admittedly an area I’m not as familiar with, but there are some sights worth checking, especially if you’re staying in this part of town.
Not only is the chicken at Giannasi fantastic, so are the rosti! It looks like chaos, but grab your number and be surprised by how smoothly the whole thing runs. Just take a seat in the little square and eat it there.
I mean, I feel like I should tell you to go to the Prada. I was a little underwhelmed and maybe you don’t have time? But parts of it were really cool! And Bar Luce is cute, if crowded, and why not get a drink or dessert. The tiramisu was very good! And the whole place is photogenic if that’s your thing.
A bit of a walk, but in the general area sorta (since what is even near the Prada), Non la solita vineria is a cute wine bar with fun snacks and lots of Tuscan wines, thank goodness. And really the bathroom decor steals the show. Trendy Lacerba is next door, so the crowds spill into the streets making for a lively evening.
CENTRO
Is always, and will be, crazy crowded. The classics are so for a reason, so yes see the Duomo and Galleria. Brave the crowds. Stop for a drink at Camparino for a break from said crowds. Browse the photo and art books Libreria Bocca. Marchesi can be a nice respite, but I also like Sant Ambroeus a bit out of the madness for a quick coffee and treat.
The Cloister is worth venturing into Centro for alone. A must shop - impeccably curated designer vintage, home goods and rad magazines and books. Plus the people there rule. Nearby Peck is also worth a pop in. The aperitivo snacks are good + plentiful and you can get the veggie chips from the store on the 1st floor to take with.
There’s what is surely an incredible Mapplethorpe exhibit at Palazzo Reale right now. I haven’t been yet but will definitely be checking it out. Open 29.1 - 17.5 2026.
NAVIGLI (kinda)
Heading south, there are several amazing high-end vintage shops - Cavalli e Nastri and the city’s other best Bivios (separate stores for mens + womens) - all on one block. Prepare to spend money.
And speaking of Navigli, if the antique market is happening while you’re here, go! While it’s usually on the last Sunday of the month, but there’s also a special Olympic edition this February: markets 8.2 and 22.2. Double trouble if you’re into vintage or all things second hand.
BRERA (and near by)
Brera is home to my favorite burger in the city - Fonzo’s. It’s a hole in the wall. A delicious dive. A perfect pitstop after the Pinacoteca, browsing the monthly antiques market, or just wondering around the neighborhood. It gets crowded and you will smell like burgers after if you eat inside, be warned and plan accordingly.
10 Corso Como is generally this direction and very Fashion Week relevant. While the boutique is a well-curated edit of top designers, the upstairs with books and beauty is magic. See what’s up in the gallery. Hang at the cafe for a while and you’re likely to see fashion royalty swan by.
Later in the evening: N’Ombra de Vin for wine and vibes. Trattoria del Ciumbia for food and vibes. And a downstairs disco club. Ideally you are dressed and smell stellar.
CHINATOWN is a short walk and Cantine Isola is good fun, wonderful wine and perfect for people watching. Stay alert to grab a seat and hang for more than a minute. Chinatown is another part of town with lots of energy and street life.
Alright! That’s a pretty nice little tour of some of the city’s hoods. Like mentioned, I kept it all walkable, but honestly one of the best things about this city is the public transportation. The metro is fast and efficient, the buses are on time and don’t blow up (hi Rome) and the trams are cute and mostly less crowded. So technically, you could tackle all this in a 3-4 day trip. Or explore some of the many other areas not even mentioned.
But don’t feel like you need to do it all. The idea is to just wander, peak in open doors (seriously, so much of Milan is hidden), and get a sense of the pulse of the city. To be open to seeing the substance beneath the style. But mostly, to drink wine and buy vintage.
* Honestly, I’ve lived here for over a year now + somehow still don’t know the neighborhood’s proper names/divisions.
I want to go!!!✨
Fabulous curation and insight!!🩵