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The Winter Olympics are coming to Italy, and suddenly I'm everyone's travel agent. I adore making a good list, but this one is no easy feat. The geographic spread of Milan to Cortina is hard to put into words.
Within the Dolomites, which is an enormous region in and of itself, you’ll want to pick one of two main areas and adventure or prepare for many stops along the way. In the summer months, it’s a different story, you can hike from town to town or make it a road trip to remember.
My best advice: pick your battles, do some heavy lifting with the newly renovated trains, hire a nice car, and enjoy the journey as much as the destination. Italy has the charm and food to carry you through any wild journey.
No matter what, you’re in for some spectacular food, stunning views, and a lot of walking no matter what. These are top of my list if I’m hitting multiple locations in one short journey. Enjoy!
MILAN
Yapa · Milan
Yapa
While your instincts in Milan might be to eat Italian all day, every day, don’t sleep on the Japanese. Yapa is exceptional, by any city’s standards. Sit bar-side for a view of the grill and ogle at the food the chefs plating. And you’ll want to order at least one cocktail.
Palinurobar · Milan
Palinurobar
There’s no shortage of vibey wine bars in Milan, from Bar Paradiso to Zazie, but the best atmosphere award goes to Palinurobar. In the summer, sit on the terrace. In the winter, cozy up under the red light of the entry signage. These guys serve tons of small producers, many limited edition, so just ask for what you like and let them guide the way. Pair it with the sardines for the perfect pre-dinner or late-night snack.
Wait and See Srl · Milan
Wait and See
This shop is the type of place you expect to quickly pop into, only to find yourself there for an hour. The owners are adorable and have curated a fantastic collection of unique pieces. It might feel like a vintage shop (it isn’t) with how much there is to discover. While you’re there, head over to the very new Minina flagship that opened across the street. They sell high-end coats and clothing that all the cool Milanese are wearing.
Antonia Stefanaki Oceano · Milan
Antonia Stephanki
Wander through a courtyard and up a flight of stairs to enter the sanctuary of Milan’s best beauty secret. Antonia offers far more than the typical facial—she focuses on facial massage for the world’s most wild instant facelift and drainage. You’ll come back to Milan just for her.
HONORABLE MENTIONS • Loste Café: Best, can’t-miss coffee shop in the city. Don’t skip the pastries. • Antonia: Great curation of modern luxury brands. • Peck: The Dean & Deluca of Milan. The packaging is iconic and perfect for gifting. • Bar Paradiso: Another great vibey wine bar. • Terroir: If you’re looking for a good food gift to take home or a very quiet place for an apero, this is your spot. • Rovello 18: Classic and downright delicious Italian food. This is true most places, truly, but this one is particularly good.
CORTINA D’AMPEZZO
Alajmo Cortina · Cortina d'Ampezzo
Alajmo
A short and doable walk from town lies this gem of a restaurant. The interiors are lovely, the food is a modern twist on Alpine classics, and the wine list is great. It’s a great spot for a large group. When it’s not too cold, you can sit on the deck and enjoy the spectacular view. Although the view through the windows from inside is not too shabby either.
HOTEL de LËN · Cortina d'Ampezzo
Hotel de Lën
While this hotel isn’t five stars like many of its neighbors, it has some of the best and most contemporary interiors in town. The rooms are large, with beautiful views from the balcony, and it has a small spa upstairs. But the real star here is the breakfast, which is a never-ending arrival of local cheeses, meats, jams, dips, breads, and pastries. The way they make tea here deserves to be seen.
Ancora · Cortina d'Ampezzo
Ancora Cortina
This hotel is an institution, but its recent renovations have made it even more visit-worthy. It’s right in the heart of town, above Loro Piana and next to the Louis Vuitton. Splurge and stay, or enjoy a very good cocktail at the bar.
HONORABLE MENTIONS • Sottosopra Casa: Cute, been-here-for-forever home goods shop, but you’re going for the socks. • Baita Fraina: Ask anyone in town where to find the best refugio and they’ll name this spot. • Mauro Guerresco: If you find yourself in need of chic, slightly boho, and infinitely wearable ski bunny attire, this is where to go (and get lost in).
DOLOMITES
Aman Rosa Alpina · San Cassiano
Aman Rosa Alpina
This new Aman property just opened and—as one would expect—it is gorgeous. Nestled in a more reserved and quiet location in the Dolomites, the hotel is located in San Cassiano, a picturesque albeit windy one hour drive from Cortina. While a stay would be legendary (say hi to the lovely GM Harry) if you can’t swing it, it’s still worth going for the spa, which is open to non-guests in the mornings (just make sure to book ahead).
Kränzelhof · San Cassiano
Kränzelhof
This place feels a little bit like a storybook: it’s part garden maze, part wine tasting, and part fine-dining restaurant. Sip and stroll through the art garden or tuck into a high-end meal in the restaurant hidden in the back. Best in the summer but the restaurant is open year-round.
Adler Lodge Ritten · San Cassiano
Alder Lodge Ritten
Frankly, this place is hard to beat. Just a short train ride up from Bolzano, this hotel is absolutely lovely. It’s all-inclusive but not in typical fashion; think top-shelf the whole way. Prepare to want everything on the menu at the spa, which has saunas, cold plunges, an infinity pool, and gorgeous hikes in every direction. The rooms are great, but if you’re really treating yourself, splurge on a private cabin.
HONORABLE MENTIONS • Rifugio Fuciade: This rifugio offers a pick-up in a snowcat for an epic arrival. • Baita Pauli: One of my favorite food spots in the region. Walk up from town in Ortisei and feast on grilled steak and great wine. Vibes are 10/10. • Restaurant Bistro Alma9: Located in Bolzano but not central, this restaurant serves great contemporary Middle Eastern food with a local twist. The cool patio in the back makes it perfect in the summer.
ALTO ADIGE/TRENTINO
Azienda Agricola Pojer e Sandri · Santa Caterina
Pojer E Sandri
Many outside of Italy aren’t as familiar with Trento Doc as they are with Champagne. Trento Doc is made in the same style and can be just as exquisite. Pojer E Sandri make their sparkling wines in this style too, with the extra benefit of washing every grape with a proprietary machine. The must-try is their Brut Rosé. They also produce a great Port-like product called Merlino that makes for an excellent gift. This is a fantastic location for an event, too; their top-floor tasting room has gorgeous views and a full professional kitchen.
Seehotel Ambach · Santa Caterina
Seehotel Ambach
Step back in time in the best way possible at this modernist landmark. Designed by Othmar Barth in the 1970s, the hotel has been impeccably preserved while still offering a contemporary touch in the rooms and spa. Go for a drink if you’re just passing through, and in the summer months have lunch on the deck overlooking the lake. But you’ll probably regret not booking the night if I’m honest.
Alois Lageder · Santa Caterina
Alois Lageder
This adorable winery and restaurant is a sixth-generation affair. Come for a wine tasting of some of the best bottles of white and red from the region. Better yet, combine a tasting with lunch. The menu is small, but the food is good. Sit inside during the colder months—but the courtyard shines in the summer.
HONORABLE MENTIONS • Scrigno del Duomo: If you find yourself in Trento, this spot on the square serves delicious, slightly modern Italian food and an epic cheese selection. • Ristorante Il Capello: Another amazing Trento spot, this place serves classics in a great environment. It’s one of our go-tos.
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