Last fall Emirates had a one-day sale - $450 round-trips to Milan - a deal we couldn't resist! We picked dates in April and gave ourselves 21 days to explore Europe. Within that time period, we considered traveling to many different countries, but eventually settled on spending two out of three weeks in Italy. Rail travel is easy and somewhat inexpensive, and ultimately the Italian destinations were at the very top of our wish list! (We spent 2 nights in Venice, 4 nights in Monterosso, 4 nights in Positano and 3 nights in Rome.)

When packing for Europe, first and foremost, ask yourself: can I run an obstacle course with my luggage? No... really. Most train stations don’t have elevators or escalators so even if you're splurging for taxis, you’ll need to be able to carry whatever you bring up and down flights of stairs, possibly while sprinting if you’re trying to catch a train. For me, this meant:

One suitcase - the largest of this trio we purchased. The key here is that many "large" suitcases are 31-32 inches, but mine was only 28 inches - it makes a huge difference. You don't need all that space because you can't go over 50 pounds without paying additional fees anyway, and the shorter suitcases give you more leverage when picking them up.
The game changer - wearing my laptop in a backpack so that my hands were free to manhandle my suitcase. I had the hardest time finding a backpack to fit my 13-inch laptop that wasn't ginormous, but this one was the perfect size. Highly recommend. (More backpack options here.)
I brought one straw hat which I tied to the backpack, so it wouldn't get crushed in my suitcase.
I usually had my small crossbody purse with me, too.

That’s it. My hands were completely free for my suitcase, just like pictured above!

Jewelry holder / Set of suitcases / Atomizer
Charging station / The perfect backpack / Privacy screen / Laptop sleeve
Travel adapter / Almonds / Larabars / Travel peanut butter

Every pound counts so I didn't pack any reading materials. Instead, I borrowed e-books from the library and uploaded them to my iPad. (See the seven books I read here.)
I put together a nighty night pack for overnight flights. I like to change into leggings, take out my contacts, use a makeup cloth to wash my face, brush my teeth, socks for my always cold feet, eye mask, and ear plugs or headphones for the white noise app on my phone.
My husband swears by this remote charging station for all his photography gear.
I swear by this atomizer for perfume - simply fill it up with your favorite scent! And only bring as much as you'll use because after about 3 weeks it will start to evaporate.
Consider bringing travel size laundry detergent so you can hand wash or use it at a laundromat.
For the bros, instead of a wallet, consider using a money belt to fend off pick pockets.
Other items to bring: a privacy screen and neoprene sleeve for your lap top, a travel adapter for the power outlets in Europe, and your favorite snacks!

Okay, now get ready to see everything I wore in 21 days. Ready?

Venice / Burano
Cinque Terre / Portovenere / Cinque Terre

Amalfi / Positano / Capri
Rome / Rome / Rome

Paris / Paris / Rennes / Montfort-sur-Meu

This was one of the best bags I’ve ever packed. Because trust me, I’ve had some real doozies! Can't count the number of times I've arrived at a destination only to be freezing to death, melting, or both. On this trip I used everything I packed (usually 2-5 times), and never wished I had brought something that I didn’t. You may not want to replicate exactly what I did here, because taking outfit photos was a major goal for us (and major fun, because we are nerds). Most of our fellow tourists were in casual athletic gear, which is what I wore for travel days. But on day trips like Capri, for example, I wore a floral maxi that was just as comfy but also made our pictures and memories that much more special. Here’s how to do it:

Dolce Vita / Coach / Nine West
Nike / Steve Madden

Pick your shoes and jackets first! How I was able to fit 21 days of clothing in one (somewhat small) suitcase was by only bringing things that worked with the same shoes and jackets. See shoes I brought above, and jackets I brought were brown leather, white blazer, denim, and black bomber.
We walked an average of 10 miles per day! I was meticulous about comfort, and only packed outfits that worked with probably not the ideal shoes for the outfit, but were super comfy.
You may not need five pairs of shoes, but bring several so if one pair gives you blisters you can easily rotate to a different pair. I tried to never wear the same pair two days in a row for that reason!
Make sure your shoes and clothes run the gamut weather-wise. I brought both sandals and shoes with socks, for example, in case the weather surprises you one way or the other. (And it did!)
Go light on jewelry. It's heavy, so I packed only delicate pieces for the most part.
Check the weather. We went in April, which meant it was both cold and hot. Hot in the sun, and cold in the shade. (At any given moment there would be someone in a bikini on the beach, and also someone in a puffer jacket!) Layers are everything, and my main rule: only pack things that look equally good with or without a jacket. This meant off-the-shoulder styles I love were pretty much off the table, because the star attraction – your shoulders – are covered up with a jacket. Another strategy: make one area of your body warm, and the other breezy (things like sleeveless with ankle boots, or a heavier jacket with sandals), so that one part of you might be warm/cold, but the other is comfortable. It helps balance out your temperature!
Wind is such an important factor to consider. You will notice that I only wore dresses that were midi or maxi length, or jumpsuits. You want to be able to sit cross-legged at a moment’s notice, and not be constantly worried about the wind blowing up your skirt.
My white blazer made it home in one piece but that was probably not the best idea. I felt responsible enough to keep it clean, but all those tourists rubbing up against me can’t be trusted. ;-)

My overall philosophy when packing for Italy is to wear the good china. This is your vacation!! You will have tons of photos and memories from this trip. Don’t be afraid to wear that maxi you normally reserve for weddings, for example, or to be a little fancier than usual. If you’re like me it will make your trip that much more fun!

Dining Tips

You will find so many wonderful Italians who speak English, however, if you want your food to go, be sure to ask for “take away.” If you say “to go” they will likely have no idea what you mean! Also tap water = aqua naturale, and rocket salad means arugula.
It’s not customary to leave a tip at restaurants, however, they pretty much all have a cover charge. Usually $3-5 per person just for sitting and eating.
Check the menu/door/window for a credit card sign. They may ask you pay cash but ultimately they take cards if listed.
You will always have to ask for the bill. The Italian culture loves to take their time at meals and they will never want to rush you! So sit there all you want and then ask for the bill when you’re ready.
Asking for substitutions is not really a thing in Italy. Even something as simple as chicken with that pasta dish, they will not hesitate to tell you no!
Bread comes with every single meal, all gelatti is good gelatti, and pizza three times a day. Also, try the hot chocolate. It’s actual chocolate in the cup and not nearly as sweet as the American version.
My favorite meal is Cobb salad, so I struggled to find restaurants offering protein with greens. That is, until I found my meal of choice: "ensalata tonno" (tuna on greens, picture below). Tuna in Italy is different than ours, it’s delicious. And salad dressing is not usually available, which means I discovered the joy of using olive oil and/or balsamic, which pairs especially well with ensalata tonno.

Train Travel

We used ItaliaRail.com for most trains within Italy, and EuroRail.com between Italy and France.
Make sure you download your train tickets to your phone before you leave, print them out, or put them in a Dropbox folder that’s accessible without Wifi.
Trains are great because you keep your bags with you, you only need to show up a few minutes before departure, no need to turn off your phone or the other time consuming rituals that come with air travel. But it also takes longer to get there via train, so there’s a trade off.
If you haven’t gone to the bathroom while the train hurtles 120 mph down the track, you haven’t lived. Bonus points for open toilets where you can see the ground underneath you.
Minimize connections if you can. The slightest train delay (and they do happen) can screw up the entire journey if you’ve got several connections. We preferred the nonstop trains so much more – you get a bit of a break from sightseeing and you can take a rest. Plus longer trips have a snack car on board with food and drinks for purchase.
The reason everyone is huddled around electronic boards at train stations is that they don't post which track your train is on until 10-15 minutes before it departs. So you will wait there, and then sprint to your track. Also - use your time departing and train number to find your track, not your destination. Everything tells you last stop, not necessarily your stop, so just ignore that part and use the time and train number to narrow it down. (Same concept as using a subway train – but if you’re suburbanites like us, we were sorely out of practice!)
Be proactive; don’t take directions from someone without checking. We missed our ferry once because the ticket window told us the wrong platform number and we didn’t double check.

Misc. Tips

You will encounter many travelers from other cultures in Italy (not Italians), and many do not believe in two things Americans hold in high esteem: 1. Personal space. 2. Taking turns. During our boat excursion in Capri, people were literally stepping on us and pushing us (kiss your personal bubble goodbye), and even if you wait your turn, they will go in front of you. It’s every man for himself!
Exchange money at your bank before you go, or use an ATM when you arrive. Avoid the exchange money windows if you can.
Bathrooms are often co-ed. There might be separate stalls by gender, but then the main area with sinks is shared. Sometimes there’s a coin deposit of .50 or 1 Euro to get in, so carry coins with you. Also, carry hand sanitizer because there is often not soap available.
Tap water is perfectly safe for Americans. Consider carrying a reusable water bottle and using the fountains you’ll see located throughout.
We are intense non-stop travelers so we needed to be reminded to consider taking a chill day. We did our laundry and basically nothing in Positano one day and it was heaven.
Rick Steves is the man. The man who loves Italy more than anyone, and has tons and tons of free podcasts and walking tours to listen to at major attractions. Buy his book or download free walking tours before you go.