The biggest factor when packing is knowing how much your airline allows. Some are 1 carry-on only for free, others are a checked and a carry-on for free. Some airlines even charge for just bringing anything on board with you! When buying your ticket, it's always good to note what the limitations are for: carry-on and checked bags, size limitations, and weight restrictions! Knowing the weight restrictions is also helpful for your return trip...you may have left space in your suitcase for 2 bottles of wine but do you have the weight to spare when it comes time to weigh it at the airport?
A smaller or carry-on bag is also helpful for just manuvering around Italy. A good rule of thumb is if you can't lift your suitcase then it's unlikely you'll get it up in the overhead storage on a plane...or up the steps onto a train...or up a hill when walking from the train to your AirBnb!
After over a decade of visiting Italy, I bring home less souvenirs now BUT I know how tempting all the goodies in Italy are. I like to bring a collapsible duffle that fits in my suitcase and I can expand it for the return trip if I need a second checked bag. The 2nd checked bag fee may be steep BUT it's often cheaper than paying to ship stuff home.
Another factor that helps me pack less is being strategic about where I stay while I'm in Italy. By that I mean I try to stay somewhere with a washing machine at least once a week! This allows me to pack less and still stay fresh! Keep in mind, we have laundry facilities in both retreat locations so don’t feel like you need to bring an outfit for everyday!
Now for the fun part...what do I actually pack?!
Even in my heavier packing years, I limit myself to 1 small suitcase (carry-on size with GOOD WHEELS) and a backpack! Within that suitcase, I try to bring no more than these items, and while using packing cubes:
And that's it! I do my best to have everything somewhat coordinate so I can mix and match too. I prefer wearing dresses and skirts during the summer so sometimes I never even wear that pair of jeans! But adjust as needed to your comfort level and stylish desires!
Within my backpack (or suitcase, if there's room), I also bring these items:
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