My First Time in Milan: A Stylish Italian Adventure

Ciao! I’ve returned from my  first-time visit to Milan.

It was wonderful, or as they say in Italian– è stato meraviglioso! It’s a sophisticated city filled with high-end fashionistas, artistic architecture and design, authentic Milanese foods and cocktails, and Italy’s largest business center.

My traveling companion was my sister N and our trip was in honor of her 70th birthday. We had been planning our vacay for almost a year and I can’t wait to tell you all about it.

My sister N and I went on a  stylish Italian adventure in Northern Italy to celebrate a special birthday

Over the next weeks, I’ll be sharing details about our stylish Italian adventure — from our walking tour of the city with a visit to DiVinci’s Last Supper and entry to the Duomo; to our boat ride on Lake Como and at-home cooking class with a Milanese chef. Then I’ll top it off with highlights from our second half which included a 4-day stay in Monterosso, one of the charming villages of Cinque Terre on the Mediterranean Sea.

Are you ready to jump in? Let’s start at the beginning.

It had been six years since my last visit to Italy. This trip I selected Milan as our base since I had never been and knew that N wanted to visit Cinque Terre, which is located on the northwest coast. I was looking forward to exploring a new Italian city. The New York Times ranks Milan among its 52 Places to Go in 2025. The Olympics will be there in 2026 – glad we got there before the crowds.

An iconic MIlan photo in front of the Duomo

An early touchdown in Milan

I booked a 4;30 pm ET flight from JFK airport in New York which landed at Milan’s Malapesa airport the next morning at 6:45 am. It was quite early but we wanted to have a full day to peruse the city.

Without much sleep, by the time our taxi (which costs around $120 euro) arrived in downtown Milan, N and I were in need of caffeine.

Boutique hotel in a great location

Our lodging for our 5-night stay was Hotel Gran Duca di York.  A smaller boutique hotel with 33 rooms, Duca is about a 7 minute walking distance to the Duomo and other Milan landmarks. The rate is reasonable for a room with twin beds (about $310 euro per night) and included a buffet breakfast – which was really good with all kinds of pastries and breads, eggs, pancakes, meats and cheeses, and of course cappuccino.

Hotel Gran Duca di York is located minutes from the Duomo in downtwon Milan

Milan Travel Tip: Hotels in Milan are very expensive. I reserved our hotel room almost five months in advance on Booking.com. When researching hotels I knew I wanted a room with two twin beds, breakfast included and in a location that was near the center of the city. I passed on AirBnb as being a first-timer I thought we would feel more comfortable with the guidance of a hotel concierge.

The only negative during our stay was the noise from the cars and motorcycles as they whizzed past the hotel each night. In hindsight, we should have inquired about the air conditioning instead of opening the windows.

Bongornio mini-walkabout around the city

The nice Duca team stored our luggage and welcomed us with a warm cappuccino and croissant. Since our room wouldn’t be ready until afternoon, we headed out for a morning walk to get a quick lay of the land. The next day we would be having a tour with a guide. With map in hand, it was pretty easy to find our way around.

Duomo Cathedral

Our first stop was the Piazza Del Duomo, where in front of us stood Milan’s famous Duomo Cathedral. The Duomo truly is a magnificent structure. In some ways I thought it looked like a gigantic sandcastle. We went back to the Piazza later in the day to see the facade during sunset — which looked even more amazing with the night sky. The Piazza is a bustling place and we were told to keep an eye on our handbags due to the pickpockets.

Piazza del Duomo with the Cathedral as its backdrop is the spiritual and geographical center of Milan

Galleria Vittorio Emanuele II

Looking to the left we saw a covered passageway with a huge arch. “That must be the Galleria, ” I said.

Galleria Vittorio Emanuele II is the most famous shopping gallery in Italy. According to history books, “the building’s neo-Renaissance style is considered one of the greatest examples of iron architecture in Europe.”

Galleria Vittorio Emanuele II is where high-end fashionistas go to shop in Milan

It was a fun place to go window shopping at the luxurious branded shops. There is Prada, Gucci, Bottega Veneta, Louis Vuitton, Chanel, Giorgio Armani, Dolce & Gabbana, Moschino, Fendi, and more.  I loved seeing the pretty spring and summer fabrics and catching up on trends for the season.

Ooh, ooh, ooh, I went back another day and splurged on a new purple Chanel lipstick. Purple is one of the in-colors for summer 2025.

Purple is all the rage for spring/summer 2025 — I bought a Chanel purple lipstick set

Teatro alla Scala Opera House

Exiting the Galleria on the opposite side is the Teatro alla Scala, among the world’s most famous opera houses. Not being a fan of opera, we passed on any tours. If you are an opera fan, you’ll want to plan a visit. There are also ballets and other concerts held at Scala.

Teatro alla Scala is the historic opera house in Milan

The Brera District

The Brera is an artsy district in the heart of the city. A few friends had recommended the district when they heard I was going to Milan. It reminded me of Greenwich Village or Williamsburg, Brooklyn in NYC.

Brera has cobbled streets lined with contemporary fashion and home shops, bistros and restaurants, and galleries and museums. The only issue with being an early shopper in Milan is that most stores don’t open until around 11:00 am. So we didn’t get to see much that morning.

The courtyard of Palazzo Borromeo D’Adda, an 18th-century palace in the Brera District

We did go back to the Brera for dinner the last night of our stay at Stendhal Brera Restaurant. It was where we had our best meal in Milan including delizioso yellow risotto, a traditional Milanese dish.

Risotto alla Milanesea creamy saffron risotto is a famous Milano dish

There’s always room for pizza and gelato

Luckily our room was available by early afternoon. We were ready for a short nap before our evening meal.

“I suggest Sophia Loren Restaurant,” said the hotel manager. “It’s around the corner.” Sophia Loren says “In my life I have had many passions, one of which is undoubtedly food. No director has ever managed to put me on a diet and I have never given up a good plate of pasta in favor of my figure.”

Around the corner sounded like a good option for two tired travelers. We shared a Bufala pizze with buffalo mozzeralla from Campania, EVO, and basil and raised a glass of Prosecco to toast our first day in Milan. “We did it, we made it here, despite our three bad knees,” I said to N. “Happy Birthday!”

A delizioso Bufala pizze

(Quick backstory: I had runners’ knee on both knees and a torn meniscus in my left knee before I left for Italy. It required two cortisone shots to get me up and walking without pain. N had a cortisone shot in her left knee too. So as you can see, we two old ladies were beyond happy to have made it to Milan.)

With the little bit of energy we had left, we walked back to the Piazza del Duomo to watch the crowds and grab what would be a first of several cups of gelato during our vacay. My favorite stracciatella (vanilla with chocolate shavings) was so good, so good, so good.

Gelato in Italy is the best

Buonanotte day one

Clocking 12,000 steps or almost 5 miles on day one, N and I were ready to relax. It was a great first day and we were looking forward to more stimulating  days ahead.

“Buonanotte,” said the Duca manager as we entered the lobby. And to all a good night.

Judi

Stay tuned: Next up I’ll be sharing our visit to the Last Supper and give a peek inside the Duomo.