What makes a vacation amazing?

amazing vacation

Being able to identify what makes a vacation amazing is a key element of travel blogging. In putting together itineraries or describing experiences, I think about the tips I might offer others that will maximize enjoyment and reduce hassle and inconvenience. But sometimes, a vacation is amazing for reasons you can’t quite describe or condense into tips.

For instance, I was in Milan last week for no other reason other than that it cost me 40 American dollars to fly there. I had been there before, and though I remembered liking it well enough, I also didn’t have any particular attachment to it as a destination. Yet, for some reason, this time around I totally fell in love with Milan. Even though my girlfriend and I have traveled together quite a bit, this was one of the best vacations we’ve ever taken together.

Is a perfect vacation always amazing?

People who are intense planners when it comes to travel probably believe that if they get to see and do everything they had planned out, they will have the best vacation. And maybe that’s true at times. But you can have everything go absolutely to plan and still be pretty underwhelmed by the whole experience. You can’t really account ahead of time how you’ll feel about the place or even who you’re traveling with.

More importantly, imperfect vacations can be amazing, too. For instance, our friends had just gone to Milan about a month before us. They gave us some awesome recommendations, including this restaurant in Como called Figli Dei Fiori. We shuffled our whole vacation around to make sure we went to Como on a day when it was open. Then we arrived, and they were fully booked. Despite this disappointment, our time in Como was magical. Como was gorgeous and romantic, and we had an awesome day.

Are unexpected surprises what make a vacation amazing?

The problem with planning everything to the last detail is that you inevitably create expectations that may or may not be met. Maybe the key to an amazing vacation is to just let it happen and experience things as they come without your pre-established impression interfering. That’s why sometimes you have fonder memories of whatever place you had ice cream one time as opposed to the museum you had been looking forward to seeing your whole life.

In part, going with the flow probably made our trip to Milan so fantastic. This was one of the few times while traveling that I had the opportunity to meet people who live there. One night when we were set to meet with our mutual friend, one of my English students who I’d never met in person reached out to see if we could get together. In the interest of convenience for everyone, we decided to get together with both of them at once. I tend to hate situations like this because they give me social anxiety. As the person closest to everyone else there, you have to put a lot of effort to create conversation among them.

To my surprise, the night was amazing. In really unexpected ways, everyone had a lot in common. My Italian student took us to a great bar I wouldn’t have otherwise visited, and with the wonderful social lubricant that is alcohol, we all had a great time.

Are the little things what make a vacation amazing?

The thing about the world’s most awesome, photographed sights is that you know they’ll be great. So just like you’d expect, the big things like the Duomo are beautiful and awe-inspiring. What you don’t expect are the small delightful things about travel that you couldn’t have possibly foreseen. Like that if you wait in line for Pizza Am to open, the owner will welcome you with a small bite to eat and a glass of prosecco. Or that the wall of the metro stop of Milan’s gay neighborhood is a giant rainbow. To be honest, I didn’t even know Milan had a gay neighborhood.

amazing vacation
Aside from the warm welcome, the food at Pizza Am is totally worth waiting in line for.

These are the small but wonderful experiences that you didn’t realize you were looking for, that just kind of happen. And maybe alone, they don’t mean much, but taken together they make for a pretty amazing vacation.

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