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From the “Duh” Department: More Travel Experience Makes You a Better Traveler

It feels like only yesterday I was packing up and returning back home after spending a month house-sitting for a friend in Milan… And yet here I am back again, subjecting myself to the torture that is Milan in August, so that I could sign a few papers and add to my Italian red tape collection.

(There’s no such thing as an Italian red tape collection, but seriously, wouldn’t that be cool if there was?)

The last time I was here in Milan, I’d been relaxed enough pre-trip to mention it on that little BootsnAll Italy guide I write, WhyGo Italy, but this time I’d just barely gotten back from an 11-day road trip with my mom, and haven’t even posted that I’m back in Italy on the Italy website. I literally unpacked the road trip bag about five minutes before I repacked it to fly to Milan the following day.

I’ve done so much travel in the last few years that I wasn’t my old stressed-out self about the quick turnaround, but I think that’s at least partly due to the fact that I was coming back to a city I know pretty well and not going somewhere new or more unknown to me. The rest, however, is due to just being a better traveler these days.

On this trip (which is two weeks long) I won’t be spending any time in Rome. As much as I’d love to visit with the friends I made there on my last visit a few months ago, knowing that I won’t be making any overnight trips during my stay in Milan made my pre-trip prep easier. I’m planning a couple of day-trips, one to a city I visited many years ago and another to a city I’ve never visited before, but otherwise I’ll be in Milan, cuddling with the portable air conditioning unit in my rental apartment and pretending it’s February.

But I digress. You’d digress, too, if you were dealing with about a million percent humidity.

It’s not just the lack of day-trips that made this Italy trip easier than it might have been a few years ago, however. I’ve gotten to be a better traveler. Back in college when I studied in England for a term, I spent a few days here and there in London – a city which overwhelmed me at the time. When I returned many years later during my honeymoon through Scotland and England, I found the city to be equally overwhelming, even though some of it was familiar to me.

I’d done far more prep for the second trip than the first, but I somehow feel like I’d feel even more comfortable and less overwhelmed if I was headed back to London anytime soon – even if I didn’t do nearly as much planning. Of course, I’d consult BootsnAll’s London travel guide (which for years was written by a London resident, and so contains some nice inside info), but I also have way more travel experience now that leaves me far less worried about the “what ifs” than I used to be.

I mean, on this very trip, I arrived on Tuesday after missing a too-short connection in Frankfurt, and my bag didn’t arrive until Thursday afternoon. I had enough stuff in my carry-on bag that I was fine, but still kind of surprised myself by not freaking out. The me of even four years ago would have been doing much more freaking out. I feel like I’ve graduated or something.

Now, I will say that while I feel like I’d be pretty comfortable being dropped into many countries and many cities around the world, knowing a few things to look for or do that would help me in unfamiliar surroundings, I also know there are some places where I’m going to want to consult a guide (or even hire one).

Leading up to next year’s World Cup, for example, I’ve been browsing through BootsnAll’s South Africa travel guide and eyeing the post-World Cup Africa tour that our Africa expert, Peter, has dreamed up for BootsnAll. It’s not just because I’ve never been to Africa that the idea of joining that tour is appealing to me, but that’s certainly part of the reason.

In short, I think that some of what makes me a better traveler now than I was four or five years ago is knowing some things to do to make a trip easier on myself – and some of it is knowing when to let someone else do the heavy lifting. It’s okay to hand over the reins now and then.