48 hours in Milan

BOSS and travel company Black Tomato partnered up to create the ultimate Milan Guide
Black Tomato x BOSS - 48 Hours in Milan

We sat down with Tom Marchant, co-founder of cutting-edge travel company Black Tomato , who gave us his take on what to eat, drink and do during a visit to Milan. A travel innovator who splits his time between his home-town of London and various far-flung destinations around the globe. Tom’s travel insight directly inspires the bespoke trips that Black Tomato create day-in, day-out. Check out his personal Milan recommendations and get inspired to visit this stylish, vibrant Italian city.

“Of all of Italy’s incredible cities, for me, Milan stirs the most senses. It’s a passionate city that’s fiercely fashionable, but it maintains a personable edge that makes it one of the most exciting and stylish outposts in Europe. The food is second to none, the architecture will leave you speechless at every turn and the art scene offers a window to some of the world’s most creative minds, past and present. Every time I return home I can’t wait to book another flight back, if you’re planning a visit any time soon, be sure to add these spots to your list.

Milan Black Tomato x BOSSMilan Black Tomato x BOSS
Milan Black Tomato x BOSSMilan Black Tomato x BOSS
Stroll through the boutiques of Corso Vittorio Emanuele

Milan and fashion walk hand in hand and my favorite off-the-track spot to go in search of up-and-coming designers is this quieter street, set back from the big hitters at Via Della Spiga. It’s also located round the corner from Cracco, offering the perfect gourmet refueling.

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  • Luini
Perfect bites for a busy day in the city, Luini makes amazing panzerotti – pillowy fried dough parcels stuffed with tomato and mozzarella. Locals have made a beeline for Luini's window since it first opened in 1888, it’s my go-to for breakfast on-the-fly.
  • Pavè
Innovation sits centre-stage at this modern take on a classic neighbourhood cafe. Focusing on creative pastries crafted from local ingredients, the founders refer to Pavè as a laboratory, but there’s nothing clinical about this friendly, bustling cafe.


  • DRY
Where Milanese pizza meets craft cocktails (focus on the first at lunchtime and the second when the sun sets) DRY is always my first stop for pizza in Milan, it’s a must visit.
  • Ratana
It’s easier to describe this hip lunch spot by my three favourite dishes: Italian risotto with squash blossoms and basil pesto, game hen with lemon-glazed scallions and mondeghili.


  • Osteria Del Treno
This is the best slow food spot in the city. Originally a club for local railway workers at the nearby Stazione Centrale, Osteria Del Treno now offers formal fare in a refined setting. If you’re visiting on a Sunday, be sure to check out the milonga tango show in the ballroom.
  • Cracco
Cracco is Milanese sophistication epitomised. Inside it’s gilded and golden, yet un-garish, and offers a creative menu which is complemented by the best wine cellars in the city.


  • Bar Luce
Colour and flavour are everywhere in this unique watering hole housed inside the Fondazione Prada. But what would you expect from a bar designed by Wes Anderson. If you’re looking for a cinematic afternoon, this is where to get your spritz.

  • Ceresio 7
The perfect place to transcend the city if you ever feel the need, Ceresio 7 is an idyllic rooftop bar with two perfect pools and the finest attention to detail.


  • Experience Italian opera at Teatro alla Scala
Nothing comes close to La Scala for a taste of authentic Italian opera. Offering a sense of place like no other Italian house, be sure to visit the Museo Teatrale Alla Scala before the show, where you’ll gain a great insight into the history of this cornerstone of Italian art culture.
  • Take a private tour of the Fondazione Prada
Once an old gin distillery, the Prada Foundation is as intoxicating today as it was in times gone by. Inside you’ll find a melting pot of works that explore the profound impact of ideas and visual perspectives upon the art world.

Tom Marchant

Co-founder of cutting-edge travel company Black Tomato

Black Tomato Co-FounderBlack Tomato Co-Founder

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