When I think about it, this trip to Malta and Italy has been in the works for about two years. First, my friend Sarah went to Malta two summers ago, and when she came back said something about having us all come to visit the next time she went. That set the seed in motion. Then, we discovered, through various smaller trips, that we travel well together. Thus, when Sarah said that she was heading to Malta this summer again, I was fully on board.

Of course, my thinking was: why stop at Malta? I’m already paying for the flight, right? I’ve got a whole summer off, right? Why not extend the trip and take advantage of already being in Europe and having the luxury of a summer vacation, and really just treat myself.

And thus we added Italy into the mix.

The itinerary is as follows: Malta for two weeks, then off to Italy for about twelve days. We’ll hit the major plays: Rome, Florence and Venice. We have day trip to the Amalfi Coast (probably insane, but what the hell??) and Verona (because I am nothing if not a huge Shakespeare nerd, and trust me when I say that I want and need the luck that visiting Juliet’s home is supposed to provide), and we’re planning a few other stops here and there along the way.

Malta will be me and Sarah – and Sarah’s family! We’ll actually be attending the wedding of one of her cousins about midway through the Malta leg of the journey. I’m excited to have a really authentic local experience, mixed in with the big sights and slightly touristy things. We have a spa day planned and boat trips, something that I really wanted to do given how much I like to be on the water, and Malta is island, after all.

Though Sarah is an old-pro at Malta (much of her family lives there), neither of us have ever been to Italy, and our thoughts these last few months have been filled with cobblestoned streets and gelato – lots and lots of gelato. And pasta. And wine. And cappucino. And… you get the idea.

In Italy we will hit Rome, Florence and Venice, spending varying amounts of time in each city. It took some strategy coordinating all the stops, but we got it down to a science eventually.

With flights and hotels booked, and the trip official, it was time to start thinking about the suitcase. As with any vacation, I wanted new fun outfits to wear, but I still had to plan to be away for an entire month while not overpacking. I decided to rely on sundresses – it’s going to be crazy hot anyway, so I might as well be comfortable. I also bought a new sunhat and a new spinner suitcase, as well as a five or six new dresses. And some skirts. And some bras (yeah, I went on a massive journey for the perfect strapless bra to wear with all these sundresses). Throw in a couple of pairs of shorts and some new strappy tank tops, and I think I’ll be good to go. And because I’m nothing if not practical when it comes to shoes, I also got a few pairs of Ked-like sneakers that I think look adorable with dresses to wear for sightseeing. I do love to walk and get lost when I travel, and I have no intentions of spraining an ankle trying to do so in heels.

I’m also not ashamed to admit that I bought an outfit purposely because I thought it channelled Audrey Hepburn in Roman Holiday to wear – where else? – in Rome. Who doesn’t want to channel Audrey Hepburn? (Probably lots of people, actually, in this Kardashion-centric world, but for me it’ll always be Hepburn.) I am a notorious overpacker, and I need twenty-six days worth of toiletries and those will not be allowed on an airplane.

I can’t promise that I’ll be doing daily posts, or even any at all while I’m actually on the trip. Honestly, I’m not even bringing a laptop, and I will want to post using pictures from both my phone and my dSLR. My goal, however, is to do a little fashion post each day if I’ve got wifi in the evenings to show off all the outfits.

My main goal is to enjoy the trip, take lots of pictures and eat, eat and eat. I’m not too worried about the internet or making sure I post about every day of the trip as soon as it happens. I’m hoping our days will be too busy and I’ll just want to sleep when we return to the hotels in the evenings. I will be journaling the whole time however (on PAPER – imagine that!) to make sure that I remember every detail (and to practice my travel writing), and I will get around to all twenty-six fun filled days on here eventually, and I’ll enjoy the rest of my summer vacation by reliving the trip and typing up the posts. Once I do, I will post them in the order in which they happened, complete with more photos than you’d ever be interested in, I’m sure.