Vacation Planning : Dreams to Reality

Vacation. Sigh. Just the word sends me off in to daydreams about lying on a white sand beach,  exploring every spare inch of a foreign city on foot and the hours and hours I get to spend planning (which I LOVE).

If I had my way, in my fab fab life, I would not work full time, and I would spend as much time as I could on vacation. Of course, this isn’t reality (yet), so I will take what I can get. Having a husband who owns his own business; vacation time can be slim, but we’ve been lucky enough in the last few years to have some exciting opportunities when it comes to vacations. This year, most of our travel has centered around weddings, which is totally fine with me because I get to spend much treasured time with family and friends.

We have a wedding coming up this weekend so naturally, I’m already wondering what vacation I can be planning next since the wedding travel has run out (oh? a cousin is getting married out West next summer? let me get on that). Just when I thought I was going to have to be scrounging around for our next vacation opportunity, all of a sudden DH and I are going with his parents to Italy for ten days at the end of the summer. As I said. I love going on vacation. But, almost even more than going on vacation I love planning them.


So of course, I’ve been crowned planning queen of this vacation. Needless to say, I will be spending hours planning where to stay, what to do, and of course what to wear! The morning after this trip was decided on, I was up at 5:30 AM researching the weather in Italy in early September (hot!) and stressing about what I would be packing. I eventually fell back to sleep but these are the things that will keep me up in the middle of the night for the next few months. Frivolous? Maybe. But that’s just me. Also, I will only be allowing myself a standard carry-on plus the standard “personal item.” Crazy? Maybe. It takes a lot of planning up front but it’s worth it. Last December, DH and I were fortunate enough to spend the holidays in Germany, Austria and Paris and somewhere along the way of planning I made the grand statement that I was going to pack for 12 days and do it all in a carry-on. DH laughed at my grandiose ideas and gave me a ‘good luck’ along with raised eyebrows.  Well. I did it and because I did it, this means that I will never ever be able to check a bag again.  So, you would think that planning for summer months will be easier. Perhaps. And we have a washing machine in our apartment in Rome (cheating? maybe). However, walking around in the middle of summer in Italy is a lot different than traipsing through the Christmas markets in Germany in winter.  I’m already picturing two outfits a day because I’m sticky from walking around. And, I live in Upstate New York. I do winter like a pro and jeans and boots and a down coat are how I define comfort.  I don’t mind summer, but my comfort zone is fall.


You’re probably asking why are you going to Italy in the summer? Don’t get me wrong, I’m not complaining…I will make this work and I will make it fabulous. Just giving you some insight in to my very full brain when it comes to things like this.

So, you can look forward to a lot of planning on my part and probably some advice seeking from those more experienced than me when it comes to summer European travel. I have to say I’m the most stressed about shoes, as I know we’ll be doing a ton of walking and my search results for “fashionable travel shoes” seems to still yield pages and pages of shoes that I don’t foresee myself wearing.  I do recognize though that there is nothing worse than walking around on vacation with sore feet, so whatever I can do to avoid this I will. I’d just like to make it look good if possible. I really don’t hope this is an impossible dream!

So there you have it. Travel planning fills my brain but I love, love, LOVE sorting it all out. Any out of the gate advice? A piece of travel clothing you can’t live without? Comments, please and thanks for visiting!