This is the third of my three part series on exploring Italy with two friends.
Milan was on my list of “must-see places before I die” and while I’m not quite ready to die, I will die happier for having seen it. (How’s that for a convoluted sentence?)
In hindsight, I realize that somewhere in my mind I had this vision that Milan was going to transform me from someone with no style or taste in clothing to a fashionable, sophisticated “My GOD, isn’t she CONTINENTAL?” type of person. Kind of like the transformation Audrey Hepburn makes in Sabrina when she leaves for Paris as a girl and returns as a woman who has grown into herself, so stylish as to be practically unrecognizable.
Alas, I should have gone to Milan as an 18 year old, or even a 20 something. I am afraid my senior citizen body is no longer suited for sleek Italian dresses and stiletto heels. But oh, I can sure admire the offerings in the shop windows while standing in my comfy running shoes.
Everything about Milan speaks to luxury, from the prices of hotel rooms to dinners out, the jewelry displayed both in stores and on people. The shops carry designer names from Bulgari, Dolce & Gabbana, Armani, Fratelli Rossetti, Gucci, Valentino, Prada—it’s a shopaholic’s paradise. We were there right before Christmas and the city was decked out in lights. Can excess ever be tasteful? Only in Milan. The Swarovski Christmas tree in the Piazza Duomo was stunning (and sparkly!) and the perfect backdrop for a social media post if you wanted to make all those girls who were mean to you in high school jealous. (Not me, of course. I don’t hold a grudge…)

The entire area around the Piazza Duomo is lit up. We were visiting in what is typically “off-season” in most places. I don’t think the Duomo has an off-season.
The first night we went to the Duomo, the sidewalks were packed with locals and tourists, and while we could have made our way through the shops in the Galleria Vittorio Emanuele, there was no way we wanted to put ourselves into that crushing mass of people during a pandemic. We’ve seen Inferno. My friend, Mary Anne, and I returned a couple of days later in the afternoon, and were able to actually enjoy the shops, take a selfie in front of the tree, and (most important) grab a gelato.
There were several Christmas markets as well as the normal outdoor markets. There’s a huge market in front of Castello Sforzesco with food, souvenirs and gifts, handcrafts, leather goods, clothing… so many little booths that you could spend the day and probably not get to them all. We wound our way through about a quarter of the market and then went into the castle grounds.
As an American, I just can’t resist a castle. In Europe, it seems like there’s a castle just about everywhere you look. Americans have to go to Disney World and that’s not even a real castle. Castello Sforzesco dates back to about 1350, and in 1450, Francesco Sforza started reconstruction and expansion of the castle for his residence. Over the centuries, it has been taken over by both the French and the Spanish, added to, damaged and restored, used as a fort and as the governor’s seat. Most of the outer fortifications were destroyed during the Napoleonic rule of Milan. The castle and grounds passed into the possession of the City of Milan after the Unification of Italy in the 19th Century.

Don’t let the door hit you on your way out. I mean, Seriously.
Many, if not most, European castles are ruins. Castello Sforzesco is very much intact and it takes little effort to imagine it as it was 500 years ago. It has towers at all four corners, thick walls (in some places, over 20 feet thick), tons of arches, and is rimmed with a parapet of crenellations. It is the medieval style castle that you see in movies, with archers shooting down from the towers and through the narrow slits designed to keep them protected.
We didn’t have time to go inside, which I regret, because it contains frescos painted by Leonardo da Vinci and Bramante. The beauty of restoring a castle in Italy in the late 15th century is that you get to hire some pretty high level designers and artists.
We also hit a few charity shops (a favorite hobby) and came away with some treasures. Mary Anne has a much better eye when it comes to fashion (and design and color and everything visual because she’s an artist) and she is able to stick her hand into a rack of clothing and pull out pure quality. I have to say, hitting the charity shops in a city known for fashion yields some incredible finds. It also helps if you are a size 8 or smaller. We are convinced that fashionable Milanese women sneak into shops and retag size 2 clothing as size 16 to make us feel bad. That’s our story and we’re sticking to it.
We found several routes back to our Airbnb which is a nice way of saying we didn’t have a clear idea of how to get back but we knew the general direction. This allowed us to discover back streets and a wonderful shop full of antiques and odd items run by an elderly man. The shop was closed but he opened it up for us and we got to poke around and chat with him. Mary Anne had been looking for a magnifying glass and she was thrilled to find exactly what she had been looking for—a one-of-a-kind antique that was perfect.
For the most part, we don’t have an agenda for every day of our trips. We tend to wander and discover as we go. Some people want to check off all the “must-sees” in each city they visit, making sure they don’t miss a thing. We’re more relaxed travelers; we’d rather get a feel for the people and the backstreets that are away from the tourist areas. We hit the grocery stores and the mom and pop restaurants and the little family-run stores. For me, the idea is to get a feel for a city, decide what I would like to investigate further on a future trip, or if I want to go back at all. Milan is a place where I will always stick out as an American. The women are far more chic than I ever was or ever will be. I’d love to go back—there’s so much more to see—but if I never make it, that’s okay, too. It is enough that I could experience Milan at its most magical time.