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2015 was Milan’s year – the Italian metropolis appeared in four of our top 10 Travel Hacker lists and garnered quite a bit of industry buzz. With all eyes on Milan and a World Expo just about to wrap up (doors close on October 31st), there’s never been a better time to explore this European hotspot. But what are the must see, must eat and must do’s of Milan? As part of a newly established employee program at KAYAK, we sent three of our own across the pond to check out what the hype is all about, so you know exactly how to make the most of your time. Travel Problem Solved.

Day 1

Ease into your exploration with a stroll through the quaint, artsy Brera district. Full of streets lined with cute cafes, shops, and galleries, it is also home to some of Milan’s great museums (notably the Pinacoteca Brera). Make sure to check out Cavalli e Nastri for vintage finds and refuel at Salsamenteria di Parma with delicious prosciutto and sandwiches.

Some plates from our delicious lunch spread!

After a long day of rigorous strolling and discovery, you’ll be ready for Aperitivo, the Italian version of “happy hour” and a must-do while in Milan. In the early evening, many eateries will offer half-priced drinks along with a buffet of snacks to enjoy. Give Bar Brera a shot – beautiful location right in the action, and a great deal!

Entrance to Mercato Metropolitano

End day one with a stop at Mercato Metropolitano – this nighttime food market has a lively but low-key vibe. The illuminated outdoor venue offers an extensive array of trendy food trucks, drink stands (including a wine vending machine!), and picnic-table style seating perfect for large groups of friends. One of our favorite spots was a grunge-chic alcove where you can lounge on industrial sized bags of lentils and milk crates while sipping craft beers and cocktails.

Futuristic wine-tasting vending machine where pre-paid “credits” buy various samples and pours – a few euro will get you plenty

Day 2

Entering the seemingly endless World Expo

The World Expo undoubtedly had a lot to do with Milan’s fast and furious rise in traveler interest and as such, was an absolute must-see for us. So on Day 2, we decided to join the masses (of tourists and locals alike), hand over the €5 for a subway pass and embark on the 30 minute journey to the Rho Fiera stop just outside the security plaza at the World Expo. After a seemingly endless hike through heavily armed security checkpoints (with a day old bottle of wine in your stomach, even a 15 minute walk can feel like a marathon), we arrived at the entrance and were stunned at the sheer size of the expo grounds. The World Expo is massive!

One could spend two full days and not see everything. Start your exploration at Pavilion Zero, the largest exhibit which also introduces the expo’s theme – Feeding the Planet, Energy for Life.

Outside Pavilion Zero

There’s a wide range of exhibits. Some feel as though they were designed in a weekend and some could remain a permanent attraction like the Eiffel Tower, a leftover from Paris’s World Fair of 1889. A favorite among our group was the Japan exhibit – waiting an hour for entrance proved worthy. Honorable mention goes to South Korea for its modern art museum-like architecture and psychedelic video installations.

Visual interaction inside the stunning Japan exhibit
The Tree of Life

When you’ve seen as much as your eyes, mind and legs can take, hop on the metro back and get off a stop earlier at Porta Venezia. Once you’ve emerged from the underground, cross the street to find Da Oscar (on Via Lazzaro Palazzi) – a truly authentic, local dining experience. It’s small with only five or six tables available – we arrived after 10pm so if you’re planning an earlier dinner, you may need a reservation but regardless, the experience is well worth it. The owner made frequent visits to the dining area for boisterous banter with his guests, making us all feel right at home.

Veal at Da Oscar

 

Day 3

The Duomo and Da Vinci’s Last Supper are Milano staples so we dedicated Day 3 to checking these wonders off the bucket list.

Tim taking in the Mailänder Dom!

The Mailänder Dom is one of Italy’s most iconic cathedrals so we decided to get up bright and early to enjoy exploring the famous Piazza del Duomo. Plan to arrive early – we strolled up around 9 a.m. to beat the crowds and hardly had to wait in line (even without reservations). This gem, located in the heart of the main piazza, is world renowned for its artistic and historical significance and let us tell you — it is MASSIVE!

View of the Piazza del Duomo in the early morning.

Be prepared to dedicate several hours to exploring – it took us about 3 hours to work our way through, but could have easily spent the whole day studying the breathtaking stained-glass windows, marble work floors, paintings, sculptures and various treasures.

We highly recommend considering the ticket option with terrace access, where you are actually allowed to climb up to the top of the church and out onto the roof. The traditional architecture is juxtaposed with modern sculpture displays, and there’s a great view looking out on the piazza and the city. An early morning well spent.

View from the terrace.

Walk to a side street about a mile from the city center to find Santa Maria delle Grazie, a modest brick church containing the Last Supper fresco. While in the church, there is a very strict no photography policy and a tight 10 minute viewing window before getting the boot. The Last Supper and Crucifixion (a slightly less well-known mural on the opposite wall) are breathtaking and rich in history, but if a long wait to enter or a tight budget are concerns, your morning might be better spent at the Duomo or Sforza Castle grounds.

Check back soon for our tips and tricks for a beautiful day on Lake Como and even more Milan. Travel Problem Solved.

Salute!

  • Chloe Gettinger, Tim Ward and Scott Brucato