Apolide Travel co-founder Chiara Caremoli, a Milan native, shares how she experiences the city, from intimate restaurants for date-nights to favorite local boutiques and overlooked sights.
1. What’s the perfect restaurant for a romantic date-night?
When I think of date night in Milan, I think about dressing up and choosing low-lit, intimate restaurants, places where you can talk, but that also set the mood.
Da Giacomo Bistrot is always my first thought. It’s very classic, very Milanese, and elegant in a 1920s way. Yazawa is also a top choice for a dressed up date; it’s refined and elegant, with a focus on wagyu and grilling at the table which makes it feel new and genuinely fun to try.
If I’m in the mood for something more lounge-like, Casa Tobago and Sogni both feel moodier: low-lit, atmospheric, and perfect when you want to set a more sultry tone.
For something more casual and more intimate, I love Vasiliki Kantina & Gastronomía and Rovello 18. They’re warm and personal, places where conversation really comes first.
2. What’s a Milanese tradition that people should experience at least once?
Going to a football match at San Siro Stadium, even if you’re not into football. The atmosphere is so intense in a way that really captures Milan and Italian culture. It’s one of those things that helps you understand the city beyond aesthetics.
3. Where do you shop in Milan when you want to find something unique?
It really depends on what I’m in the mood for, but Milan is incredible if you need pieces that are rare.
SO-LE is special because it’s a one-of-a-kind boutique creating handmade leather jewelry and accessories, and it’s exclusive to Milan. Timothy Oulton is a hidden gem for statement furniture that blurs the line between design and art, and Michel Leo has some of the most beautiful antique furniture I’ve seen in the city.
I also love Le Nom for their handmade leather bags, especially because you can personalize them and have whatever you want painted directly onto the bag, while Motel Miro is great for affordable, hand-painted ceramic home pieces.
10 Corso Como is always a go-to when I’m looking for something a bit out of the ordinary from luxury designers, and DMAG is chaotic in the best way, it’s a warehouse of vintage designer pieces where you never really know what you’re going to find.
I also love going to the weekly markets. They’re such a goldmine for basics and knitwear—especially the Mercato di Via San Marco, Mercato di Viale Papiniano, and especially the Mercato di Monza if you feel like going a bit further out.
4. Where do you go for aperitivo when you’re meeting friends, not entertaining visitors?
If we actually want to talk and catch up, we usually end up at TakeAway Bistrot or Tommasi Milano—very relaxed, and spacious outdoor seating.
If it’s more of a “start of the night” situation, then Altrimenti Mixology Art or Onda Listening Bar for more energy and a social crowd.
5. If someone is visiting Milan for the second or third time, what would you tell them to do differently?
There’s lots to see and do beyond the main tourist attractions in Milan, you just need to know where to go. Instead of focusing on the major museums, I’d suggest underrated ones like the Bagatti Valsecchi Museum or Palazzo Clerici, which give you a tangible idea of Milanese taste and history.
I’d also encourage exploring neighborhoods that are often overlooked the first time around. Chinatown Milan is great for casual, affordable meals and walking around, and Colonne di San Lorenzo is perfect for vintage shopping and getting a sense of everyday local life.
Day trips make a big difference too. Monza is an easy option, you can visit the Villa Reale di Monza and wander the historic center, or you can head to Bergamo Alta or Lake Como for a change of landscape.
And finally, I’d build in time to slow down. De Montel Terme is a great reset, and in spring or early summer I love booking a picnic at Cascina Pizzo, just outside Milan, when the tulip fields are in bloom.
6. What’s your favorite place for a drink after dinner?
It depends on the mood. If I’m in the mood for something polished, Bamboo Bar at the Armani Hotel is always a classic, and Rumore at the Portrait Hotel is great for live jazz and a social crowd. Officina is an eccentric cocktail bar while BY IT has that low-lit, slightly private lounge atmosphere I love.
If I want something more casual and energetic, I usually end up in Brera or Moscova—around Via San Marco, Via Solferino, or Piazza del Carmine—where bars are tiny and everyone spills out onto the street. And for a similar vibe in a different part of the city, the Cinque Vie area is great, especially spots like Flow or B Café.
