If you’ve been getting my newsletters or following along on Insta, you know I got back from my honeymoon in Italy last week!
I’ve gotten a bunch of questions about the trip so I thought, why not share our itinerary here - along with some travel tips and useful nuggets that may be helpful if you’re planning something similar.
Full disclosure: this was my first go at spending a considerable chunk of time in Italy. I’m not an expert whatsoever, making this a very subjective and non-exhaustive guide.
Before we dive in… when you go to Italy, it’s hard not to think you’re doing everything wrong back home. “Why don’t I start my days with a frothy, rich cappuccino instead of my utilitarian coffee with stupid flat milk?” “Why don’t I have a lengthy aperitivo with my husband every night while we discuss the meaning of life and stare at each other?” and my favorite, “Why don’t I just… sit more?”
A trip to Italy - or anywhere, really - is an opportunity to reflect and maybe even bring some new habits back. It’s not just about checking landmarks off a list.
Our Itinerary
We began our trip in Milan, where we spent 3 days. We then took a train to Cinque Terre, where we also spent 3 days. Then we took a train to Florence for 4 days, and finally a train back to Milan to catch our flight back to NYC. It felt like a good amount of time to get a decent feel for each of the three places.
Things to Know About/Impressions of Milan
I hadn’t given Milan much consideration prior to going. To be honest, one of the reasons we chose it was because it was the cheapest round-trip flight to Italy we found without layovers.
We were both surprised by how much we loved it. The pace of the city, the mix of old and new, and the cafe culture reminded me of Paris, while the contrast of charming old streets and Fascist-era buildings felt like Odessa (my home city in Ukraine). Outside the city center (Duomo area), it felt less touristy than Florence and Rome.
Milan also feels more people-friendly. It has wide sidewalks, making it comfortably walkable - which can’t be said for Florence, where you share the narrow streets with bikes, Vespas, and cars. Milan also has an easy-to-use metro system.
We stayed at a hotel (linked in the pdf below as a special bonus for my paid readers 💕) near the Central Station.
Not to Miss In Milan
The main attraction is the Duomo and it is 110% worth it. The building - inside and out - is truly awe-inspiring. (It took nearly 600 years to complete and has a whopping 3,400 statues!)
After you climb the 256 stairs to and from the terraces, reward yourself with a cold spritz at the Terrazza Aperol, which overlooks the grand building itself.
For another day, I recommend Fondazione Prada, a sprawling modern art museum commissioned by the Italian fashion house - with a Wes Anderson-designed cafe attached.
At night, head to the Navigli canal, which is lined on both sides with bars and restaurants. Come for aperitivo and people-watching, stay for dinner and the lively after-dark energy.
A Note on Restaurants
Tbh, it’s hard to have a bad meal in Italy. Avoid tourist traps, though, (usually near the big attractions) since the food is overpriced and subpar, and the atmosphere is unwelcoming. My suggestion is to not go out of your way to make it to the “famous” places but rather seek out lesser known spots where locals go. They almost always have better food, service, prices, and ambiance. Ask your hotel concierge or Airbnb host for recs in their area.
Nonetheless, I compiled a couple of our favorites in a Google map at the bottom of this newsletter (also for paid subscribers).
Since dinner in Italy is presumed to last ~2 hours, there are likely to be only two seatings per night. Call/email a few days ahead to reserve a table.
Things to Know About/Impressions of Cinque Terre
Cinque Terre is a chain of “five villages” on the coast of the Ligurian sea. They’re connected by train, ferry, and a breathtaking coastal hike, so you can technically visit them all in a day. But, it would be exhausting and you’d kinda miss the point. (This vintage Rick Steves video gives a great overview.)
We chose Monterosso Al Mare as our “homebase” - the resort-iest of the five and the only one with sand beaches - and visited a few of the other towns by hike and ferry.
Hands-down, Monterosso is one of the most beautiful places I’ve ever visited. It’s got charming winding streets, green rolling hills in the distance, and stunning sea views with clear blue water breaking on rocky cliffs. It’s family-friendly, so there are no late night clubs (a la Mykonos) or wild drinking.
Not to Miss in Monterosso
The food is understandably seafood-heavy, which I certainly indulged in. Liguria is also the birthplace of focaccia, so you’ll find lots of it around town (focaccia sandwiches seem to be the standard lunch).
There is a public pebble beach where you can lay out and swim for free. The other [sand] beaches offer chair rentals, as well as waiter service, which at around 15 euro/person is well worth it.
If you’re physically able, we highly recommend a cliffside hike between two towns (we went from Monterosso to Vernazza). The views are unbelievable. It may be just over 2 miles, but it’s mostly uphill on stairs/narrow paths, so it’s not for the faint of heart. Wear sunscreen and a hat, and bring water.
Things to Know About/Impressions of Florence
Florence is the birthplace of Renaissance art and known for its old-timey charm - tiny winding streets, green shutters, and all. The oddest thing about Florence was the weather, which was identical for all four days. Gray in the morning, hot and sunny midday, followed by an hour or so of rain, then a cool dry evening. It didn’t get in the way of sightseeing, but did make getting dressed more challenging.
The city center (Duomo/Ponte Vecchio area) is extremely crowded with tourists. Although there’s so much to see, the constant flow of faces, backpacks, and selfie sticks was a bit exhausting. My advice: conserve your energy and don’t spend too much time there at once.
Not to Miss in Florence
Strolling by the Arno river makes for a pinch-me, “Wow, I’m in Italy” moment.
Compared to the Milan Duomo, the interior of Florence’s Duomo struck us as scarce, which was annoying to learn after we waited an hour to get in. Giotto’s Bell Tower, though, was worth the climb - the views were fantastic.
For a respite from the city center, I really liked Boboli Gardens - a massive Versailles-like space open since 1766.
We did visit Uffizi gallery (one of the main art collections in the city), but in hindsight, I would’ve skipped it. It was extremely crowded, making it impossible to enjoy the art (even if it was “The Birth of Venus”).
Since Florence is in Tuscany, I recommend booking a wine tasting in the Chianti hills. We found a group tour through Airbnb Experiences and it was one of the best memories we made. (Tour linked in the pdf below.)
General Tips and Reflections
Don’t overbook yourself. It’s tempting to pack out a full itinerary of tourist attractions, but my advice is to leave time to just chill. Wander the streets, sit in cafes, let yourself be charmed, chat with locals. I promise: your best memory is not going to be the day you spent two hours waiting to see Michaelangelo’s David.
Learn a few phrases in Italian. Manners are a much bigger part of European culture than American and people really appreciate when you make an effort. If you have any knowledge of Spanish or French, you’re halfway there. A simple buongiorno and grazie can go a long way. YouTube is your best friend here.
Check your credit card for fees. Gone are the days of cash-only, need-exact-change-for-every-cafe travel. You can pay with a card for everything but remember that most American cards will charge you ~3% for every transaction abroad. Check with your bank before leaving.
Yes, you can travel with a carry-on. Although many might use a Euro-trip as an opportunity to bring all their favorite outfits and 10 pairs of shoes, it would not be wise if your plans involve trains, stairs (like our Florence Airbnb), etc. Embrace being an outfit repeater - you can always wash a t-shirt in the hotel sink…
Click to check out my Italy Google Map 🌎
Get all the links + resources I mentioned above in a printable pdf:
I’d love to know your Italy recs and travel tips! Tell me in the comments.
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