I had two weeks off between jobs in October 2021 and with travel starting to open back up, I decided to take advantage of it with a 10 day trip to Italy.
I planned this trip in about 3 weeks, but I crowdsourced so much of it from family and friends so it ended up being absolutely perfect! I think this is the itinerary I get asked for the most from friends and colleagues, so I figured it should be the first one I post here! At the bottom of the post I have a PDF of the exact itinerary so if you (like me) hate reading all this ish feel free to scroll down there.
I started in Milan where I spent less than 24 hours. The flights were more reasonable flying into Milan than into Florence and I wanted to fly in and out of different airports to avoid wasting time traveling. This was the trip that finally convinced me to get a Delta credit card (#nofreeads) just to get those sweet sweet points.
I stayed in this really charming AirBnb and while I usually try to avoid AirBnb's when traveling alone, this one felt very safe with separate keys needed to get into the building and into the apartment. The apartment itself was on the small side (would be a tight fit for two people) but for my purposes it was perfect!
After grabbing a quick bite to eat, I headed to the Duomo to do a cathedral and rooftop tour that I had booked in advance. The views were incredible and the architecture was so cool. You get to actually walk on the roof and see the intricacies of the details.
I then did the thing and walked through the Galleria Vittorio Emanuele II (which you can actually see in one of the pictures above). If you're into luxury shopping and that's why you're going to Milan, then great! You'll love this! If you enjoy watching influencers shamelessly take photos that involve getting in everyone's way and then running back to their open suitcase to do a quick change before getting more content, then also great! I am unfortunately not into either of those things so I did a quick walk through to see the vibe and then skedaddled.
I did take the cheesy next step of going to the Aperol Cafe. Is it a tourist trap? Yes. Is it overpriced versus the 1000 other Aperol Spritzes you can get throughout Milan? Yes. Do you still get a helluva view of the Duomo and do I recommend going? Also yes. The first pic of this post was from there. The view was amazing and the aperitivo was pretty darn good too. I posted up here for a bit to do some serious people watching and reading before heading on.
The rest of the itinerary is much more ~walking based~ unless you're the kind of person that needs to read every single plaque at a museum (eek). I basically just walked through the Sforzesco Castle to see what the dealio was and then was on my merry way to the Arco della Pace for more people watching. It was a lovely little stroll through the park but at this point my feet were straight up not having a good time and I needed a nap.
My favorite thing to do on vacation is take a quick lil siesta after my daily activities before getting ready for dinner. Usually I grab a bottle of wine and some snacks on the walk home so I can revive myself post-nap. I grabbed a bottle of red from Tacito (and a corkscrew!) and headed home.
Dinner was at Ostaria della Darsena. This was a great first meal in Italy. I got this mouthwatering plate of risotto with a glass of red wine. The highlight of the meal though was their tiramisu, which was the dessert that inspired me to have tiramisu every night of my trip chasing that high. Also like looooook at this freakin risotto. (There is no picture of the tiramisu because I INHALED it.)
That's a wrap on Milan! The next morning I was on a train to Florence...
Milan Itinerary:
10am: Land at MXP
11am: Take train from MXP to Milano GP and then take the Green M line or walk to AirBnB
12pm: Grab a bit to eat and walk around (honestly I think I got some weird panini to go)
1pm: Duomo Cathedral & Rooftop Tour
2pm: Walk through the Galleria Vittorio Emanuele II
3pm: Have an aperitivo at the Aperol Cafe
4pm: Walk through Sforzesco Castle and then through the park to people watch at Arco della Pace
5pm: Grab a bottle of vino at Tacito and head back to the AirBnB
6-7pm: NAP AND RALLY
8pm: Dinner at Osteria della Darsen
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