Renowned for being the capital of ‘La Moda’, where the overly fashion conscious sip cocktails in fancy bars against grey skies and comparably grey buildings. This is not a city people particularly flock to for a holiday, but delve a bit deeper and you will find there is more to this amazing city than meets the eye. It’s not just high fashion; cool hipster bars sit alongside down-to-earth wine bars, which rub shoulders against trendy independent boutiques selling beautiful handmade jewellery and clothes at not such crazy prices. This is somewhere that, once you venture further than the cathedral and its surrounding luxury, is a city that might actually throw a few pleasant surprises your way.
Stay
A twenty minute walk from the Duomo, south of the city, the Navigli area is not considered majorly central but you could easily spend a few days exploring this trendy area and it makes a great base, due to its nightlife and picturesque surroundings. The Navigli is a series of canals, and the Navigli Grande canal is lined with bars and restaurants providing a buzzing nightlife continuing well into the early hours.
‘Maison Borella‘ is bang smack in the thick of it all. To the extent that if you’re a light sleeper I wouldn’t opt for one of their canalside rooms; choose instead an internal room overlooking a picturesque courtyard. Or brave the atmosphere of the canal and wake up every morning to a gorgeous view. This is a beautiful four-star boutique hotel, and my balcony overlooking the canal made for some great people watching well into the wee hours. With a comfy communal lounge area full of soft plush sofas, there is also a restaurant ‘Restaurant Bugandé‘ serving delicious food and in summer there is al fresco dining in the courtyard. Come here to experience a different side to Milan.
The balcony of my room overlooking the canal. 
The internal rooms facing the courtyard. 
The comfy lounge area of the hotel, overlooking the internal courtyard. 
Restaurant Bugandé at the hotel had quirky and comfortable decor and the food was delicious.
Lunch
Just down from the Navigli and near Porta Genova, an area which has some great shops on the streets leading away from the station, is the incredibly cool Japanese concept store ‘Tenoha’. A co-working space with a cafe and restaurant and a shop selling beautifully stylish and minimalistic goods, this place is an experience. Stark but stylish decor, and a menu inspired by the street food of Japan, it just exudes trend appeal.
Tenoha is also a co-working space, with an outdoor courtyard for the summer. 
A Japanese concept store, Tenoha also has a shop selling beautifully crafted and original items.
Aperitivo
Milan is the grand dame of aperitivo hour. They invented it, they know how to do it, and they know how to do it with style. Between the hours of 6-8 bars are buzzing with the Milanese looking sleek whilst enjoying nibbles and cocktails in suitably fashionable surroundings. In Milan aperitivo is taken pretty seriously so it’s best to book, especially in the more upscale bars. The area around Arco della Pace has some suitably fancy places to try. Or head to La Rinascente (Piazza del Duomo), Italy’s luxury department store. They have a rooftop bar overlooking the Duomo, perfect for a spritz with a view.
For something more casual I recommend ‘Enoteca Don Pietro’ (Via Vigevano, 9 open 4.30pm-12, closed Sunday) near the Navigli. Small and brimming with a bustling ambiance, the owner is friendly and he offers a delicious selection of wine by the glass or bottle and a variety of small tapas style bites. Whilst not an aperitivo as such, it makes a great place to stop for some wine and nibbles. Always busy, you might have to fight for a seat. But once you find it you’ll be loathe to move from it until closing time!
Dine
Two Milan specialities are saffron risotto (risotto allo zafferano) and veal in breadcrumbs (vitello alla milanese). Neither have great aesthetic appeal but they taste pretty delicious and are worth trying, and whilst a plate of rice without any veg doesn’t seem overly appealing, it really does hit the spot with its rich flavour. If you’re looking for a casual but atmospheric place to dine, try ‘Le Belle Donne’ (Via Tortona, 28 open daily for lunch 12.30-3.30, dinner 7.30-11.30) not far from Porta Genova. Reminiscent of an Italian restaurant from the nineties, with black and white framed pictures of celebrities, and the constant dimming of the lights as the waiters visit various tables with sparklers whilst singing happy birthday to some cheesy background music, this place was fun. Everyone was welcoming and extremely friendly, the food and wine were delicious and for Milan it was very reasonably priced. Myself and my friend had a great time here, felt utterly welcomed and, despite it being the weekend before Christmas, everything ran like clockwork. Definitely one to try, and they also have a more casual pizzeria next door also. Booking essential.
Shop
Where not to shop is the question! Milan has everything you could ask for when it comes to shopping. High-end fashion, designer shops, independent boutiques, as well as the high street. My favourite area has to be Brera. Quaint cobbled streets leading away from the Teatro della Scala are full of luxury boutiques. Whilst expensive they are unique and often independent, and even window shopping is a pleasure in this area. If you head over to Corsi Garibaldi nearby you’ll find a few more affordable places, as well as some nice bars. Be sure to stop for a glass of wine at Procacci (Corso Garibaldi, 69 open 12-2am closed Sunday), a gorgeous wine bar with a great atmosphere.
If high-end is what you’re looking for then you need to head to ‘Galleria Vittorio Emanuele II’ and the surrounding area near the Duomo. The gallery is a beautiful covered passage and an eye-wateringly beautiful marvel of architecture, and the prices of the shops might make your eyes water too. But when in Milan do as everyone else does, shop till you drop!
If you’re looking for something a bit edgier then head to Via Ticense and follow it down to the Navigli. Explore the boutiques of this area that continue over to the Porta Genova area. A bit more urban and gritty, this is an area where you can find something really unique that definitely can’t be found elsewhere. And of course all the great bars in this area make perfect respites for a post-shopping glass of wine!
