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The joy of traveling alone in Milan

Updated: Jun 15, 2022

I take more in. I hear more. I see more.

The first time I traveled alone it was not planned that way. On September 9th, 2001, I flew to England to see my relatives for a few days before a friend from Wyoming was going to meet me in Prague. And then we were planning to travel to Italy and Paris as well. Back then I worked in retail marketing for Discovery Channel and I could have four weeks off in a block for vacation, which was amazing!

We all know what happened on September 11th, which completely shut down travel from the USA to other parts of the world. My friend was unable to meet me, and as this vacation was already booked and paid for and I couldn't travel back home - I just forged ahead on my own.

It ended up being an incredible, life-changing trip. Everyone I met in Europe was so loving and kind as they knew I was American and trying to grapple with the tragedy our country had just faced. I was greeted with hugs from complete strangers, saw many beautiful memorials full of flowers for the US, and leaned into the solitude of being on my own in a foreign place.

Many memories were made that I still cherish today. I traveled again to Europe the following year in 2002 and spent half the trip alone, and the other half with friends and family. And that's how I like to travel now.

My foreign trips were on hold for a while when I moved, changed jobs (goodbye 4-week block vacations!), and started a family. Fast forward 20 years, and now I’m traveling back to a foreign country alone, and one I love deeply. Italy.

The sounds of Italian chatter from people passing by, the ringing bells from the duomos, the street noise, singing from the alleys and windows, and children laughing. Awww, a little slice of heaven.

I see more intensely when I am alone - colors are brighter (or is that I notice them more!), the details on the buildings, the gargoyles in the sky! Just incredible!

Duomo of Milan

I eat when and where I want, walk for as long as I want, go at a slower pace, and fill my days by soaking it all in. I enjoy striking up conversations when I want to and have met the most lovely people this way.

When I was younger, one of the hardest things for me was to walk into a restaurant confidently and sit down and eat by myself. Now that I’m in my 50s, I have absolutely no problem doing that, but certainly, 20 years ago, it was a difficult thing to do. So having a sketchbook or a diary was a very handy way to occupy myself!

These "alone" days are when I sketch more and paint in my journals.

Here are some more photos of Milan and a few sketches:

There’s a hidden botanical garden inside the city of Milan - Orto Botanico di Brera. It’s absolutely stunning, and I’m so glad I finally found it after walking around in a few circles!

This is a watercolor sketch of one of the walls. I highly recommend it to anyone traveling to Milan.

I also explored Leonardo DaVinci's Casa and Vineyard in the middle of the city!

The gardens were incredible!

I was only in Milan for 2.5 days, but clocked 27 miles walking! Beautiful weather to just walk and walk and take it all in!

Here are a few more fun photos (I have 100's to choose from - lol)

Flea market, roses, my hotel right around the corner of the Duomo; Gran Duca di York Hotel

Have you been to Italy? I'd love to hear your favorite spot as I am planning my 2023 trip!


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I loved looking at your pictures from your trip! I just returned from Lake Como and Milan myself! You should definitely visit the old city of Lake Como next time. My husband and I loved it!


Yummy treats, colors and textures!


Lynne Davey
Lynne Davey
Jun 18, 2022

This was so fun to read. I agree, traveling alone is very special. You certainly do see things differently. I always make notes of what I want to tell my husband about though. Loved looking at your journal sketches. Can’t wait to hear where you are going on Italy. I’ve only been to Lake Como, Varenna, and Venice. Beautiful country indeed.

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