I’ve been dreaming about traveling to Italy ever since I can remember. Maybe it’s the Italian in me, but it has always been at the top of my travel list. So on the occasion of my 27th birthday, I finally decided to take the plunge and book a flight. After some deliberation, my boyfriend, Holden, and I decided on four cities: Cinque Terre (which is really an area with five adorable towns!), Florence, Capri, and Rome. While they’re all in different regions, we were determined to see as much as possible during our two-week getaway. I knew packing for 14 days wasn’t going to be easy, but I focused on simplicity, comfort, and threw in a few standout accessories for good measure. For the most part, I stuck with the basics and added a few layering pieces, as well as pieces that could easily make up an entire outfit, like dresses and rompers. Since this trip was going to be a non-stop adventure, I wanted items I could put together effortlessly to make for a stress-free vacation. Here’s what I landed on.