Everyone knows that person who spends weeks sniffing around travel blogs, going deep into Tripadvisor rabbit holes, collecting Google docs from friends of friends, and creating A Beautiful Mind–style spreadsheets to come up with the best vacations and itineraries possible. In this recurring series, we find those people who’ve done all the work for you and have them walk us through a particularly wonderful, especially well-thought-out vacation they took that you can actually steal.
With a work trip in Geneva wrapping up just as Miart (Milan’s annual contemporary and modern-art fair) was beginning, it felt like the perfect time for creative director and photographer Diana Bartlett to make her eighth trip to Milan, one of her favorite cities. “I’ve always loved the pace, how every day the routine is almost the same,” she says. “It’s calming to be on Italian time.” After months of consecutive work travel, Diana settled into slower mornings with room service in bed and three cups of coffee before walking out the door (this is the espresso capital, after all). As a self-proclaimed foodie, her days revolved around meals, like the ravioli with fried sage at her favorite Italian restaurant in the world, and were balanced with exploring the city’s ever-impressive art scene. “The architecture and materiality of this city are always inspiring,” says Bartlett.
Day 1
2 p.m.: After a long lunch in Geneva, drive to Milano
It’s about a three-hour drive if you’re going fast. I was in Geneva for work the week prior and decided to drive with local friends who had their own car there. You’re driving through the mountains sometimes with no service, so make sure to download your road-trip playlist ahead of the trip. We listened to lots of karaoke classics and sang our little hearts out.
6 p.m.: Arrive at Principe di Savoia
Principe di Savoia (Piazza della Repubblica, 17) is a pretty ritzy hotel with a great gym and 24-hour room service. Ask for an unrenovated room if you stay here, but to be honest, I prefer to stay in an Airbnb slightly more central because I like to have a kitchen. But if you’re more of a hotel person, I love the new Vico Milano (Corso Genova, 11), which just opened last year. It’s a seven-bedroom boutique hotel and is the passion project of Neri Baccheschi Berti of Castello di Vicarello in Tuscany. Neri wanted to create an ultraboutique guesthouse feel, which he’s done beautifully in partnership with Sicilian architect Giuseppe Alito. It feels like a very chic home away from home.
9 p.m.: Taxi to Da Giacomo because you know you’re already running late
Ideally I like to walk, but I’m always running late (especially to dinner). Da Giacomo (Via Pasquale Sottocorno, 6) is always my first stop in Milan so I feel like I’ve seen a bit of the scene and Italian elegance. There’s not a better people-watching restaurant, from fashion week to Salone to a regular night — there’s always something to admire here. They are also home to the best espresso martini I’ve ever had in my life and the loveliest manager, Pajja, a legend! After dinner, we walked home past Villa Necchi in Porta Monforte, which is one of the most beautiful neighborhoods in Milan.
Day 2
Noon: Visit Villa Necchi
I visited Villa Necchi (Via Mozart, 14) for the first time this trip, which is the most beautiful house in all of Milan. It was designed by Piero Portaluppi in the 1930s for sewing-machine heiresses Gigina and Nedda Necchi and Gigina’s husband Angelo Campiglio. The Art Deco design was a modern departure from the decadent palazzos of its time and features a beautiful garden and a collection of art by Picasso and Matisse.
The home is lush and elegant; it showcases the materiality of Milan — grand marble bathrooms, elegant canvas coverings, and velvet couches, making it very easy to imagine all the swanky fêtes that were thrown here. You can book tickets for a self-guided tour here. It was also the home in Luca Guadagnino’s 2009 film I Am Love, which is exquisite and a must-see.
1:30 p.m.: Head to lunch, walk past the Duomo
I’ve been to Milan quite a few times now. I’ve spent weeks on end there and out every meal of the day exploring all the right restaurants and wandering into even better ones. Trattoria Milanese (Via Santa Marta, 11) is still the perfect place for a solo lunch or a lunch date. Order the vitello tonnato, asparagus and parmigiana, risotto with osso bucco, and the milanese.
7:30 p.m.: Get to La Latteria right when they open
It’s really nice to be at La Latteria (Via San Marco 24) because it’s completely authentic and you feel like you’re in nonna’s kitchen. On day two of my trip, I usually like to have an early night so I don’t burn out midway through (this is only something I’ve learned recently). La Latteria is perfect for that — a big bowl of pasta and a few glasses of wine before a good night’s sleep.
Day 3
5 p.m.: After a long walk, grab an apperò
I took it easy today, walked around without a map, just roamed, which is my favorite way to be surprised in a city. I leisurely made it over to the Milanese institution, the iconic Bar Basso (Via Plinio, 39). I usually go pre- and post-dinner, but it felt right to do a pre-art-viewing cocktail here with an Italian friend who is a painter. I always go for a spritz, but they’re also famous for their negroni. Please steal my entire vacation, but map it out first because Bar Basso is across town from Miart! A mistake I will not be making again.
7 p.m.: Go to the opening of Miart
Get someone who works in art to show you art. For this evening at Miart, I was in good company as the friends I was with are a painter and gallerist, respectively; they were the perfect tour guides to walk around with. Grab a glass of Ruinart from the lounge before your tour. The Mapplethorpe solo at Franco Noero was incredible, as well as the Salvo sculpture at Norma Mangione and Giacomo Balla at Galleria d’Arte Maggiore G.A.M.
9:30 p.m.: Settle in for a big dinner at La Libera
La Libera (Via Palermo, 21) is one of the best places in Milan for a big group dinner, casual enough that you can add an extra seat and iconic enough that you really feel like you’re in a spectacular room. The owner, Italo Manca, has a lot to do with the vibe of this place, he is one of the most elegant and well-dressed men in Milan.
Day 4
11 a.m.: Have breakfast in bed
My job requires a lot of travel, a lot of working weekends, and no real day off. I’m on a plane more times in a month than I can count on one hand and likely not home for more than a week straight. So when I can, I take the opportunity to just lay in bed — especially in a luxurious hotel room. When ordering room service, I always get a pot of American coffee so I can get my three cups in without having to order a bunch of lattes. I take each cup with a heaping teaspoon of honey and milk.
1 p.m.: Hit the galleries because you didn’t see enough art yesterday
Once I’m fully caffeinated, showered, and dressed, it’s time to gallery hop. We went to Galleria Massimo De Carlo (Viale Lombardia, 17), which is by appointment only, and saw “You” by Maurizio Cattelan. His work is incredible and so is the interior architecture of the gallery, so don’t miss it — the same architect (Piero Portaluppi) designed Villa Necchi.
4 p.m.: Snack at Bar Luce and visit Fondazione Prada
It’s a spritz, prosciutto and mozzarella, followed by stracciatella ice cream at Bar Luce inside the Fondazione Prada (L.go Isarco, 2). Ms. Miucca Prada was also there, dining at a corner table by the kitchen pulled out just for her that disappeared when she did. Pro tip: If you tell them you’re celiac, they’ll make you a plate instead of a panini (if you’re not celiac, they only have paninis). Once I’m two spritzes deep, it’s time to see the show. Make sure you see what’s currently on view as well as the permanent collection. For tonight, we’re taking it easy to prepare for our little day trip tomorrow.
Day 5
9 a.m.: Drive to Torino to see Mollino’s house
It’s a two-hour drive to Torino; it’s easy and worth it. We went to see the Italian architect Carlo Mollino’s house, which he designed as a late-19th-century villa; it is now a museum, Hotel Casa Mollino (Via Giovanni Francesco Napione, 2). It’s a private tour, so book in advance, and they do not allow photographs of the space. I snuck this one for you. The space isn’t large, but the tour is about two hours long, and you get an extremely educational explanation of Mollino’s life and work.
Remember that a good lunch in Italy isn’t served unless you’re there before 2:30 p.m., so keep this in mind if you want to have lunch in Torino. We opted to walk around instead and stopped at an amazing Italian pasta shop and deli, Pastificio Ferro (Via Michelangelo Tonello, 2), specializing in Piedmontese cuisine on our way back to Milan. They have incredible fresh pasta and sauces to bring home and lunch or snacks for the road. Make sure to grab what’s specific to the region. P.S. This is also truffle region, so it’s best to go in autumn.
8 p.m.: Order ravioli with sage for your last dinner in Milan
Always save the best for last. Antica Trattoria della Pesa (Viale Pasubio, 10) is hands down my favorite Italian restaurant in the world. Everything about this restaurant is perfect — from the Italian woman at the front desk in full Pleats Please, the linen coverings on the window, and how they bring all the food out on a metal cart. It truly feels like you’re in a film of old-school elegance. And you could watch the clientele speak Italian like you’re watching a screen all night. Order the ravioli with fried sage, risotto alla milanese, and end with the flan.
Diana’s Milan packing list
I only ever travel with a carry-on, so it’s important to have a good one!
Nothing soothes dry skin and gives an instant glow like this cream.
You can’t go to Bar Luce unless you’re repping Prada — what if you run into Miuccia like I did?! But really, this bag is the perfect size for sightseeing. It fits a camera and some snacks.
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