Should you go to the same vacation spot again: The pros and cons

One of the most appealing parts of traveling (for most people) is seeing a place for the first time. It’s hard to match the excitement of landing in a faraway airport and seeing new kinds of trees and buildings and even beaches. Some people love that feeling so much that they only go back to the same place when there are no other good choices.

But other people tend to find a place they like and then go back every year, at least until they get bored. Some of these are people who’ve been tricked into buying a timeshare, but others just really love the familiarity. Below we’ll discuss the good and bad points to help decide whether it’s a good decision for you.

Pro: You can really get to know a place by going again

One argument is that if you really like, say, Jamaica, the first time you go there then going again will give you a chance to get to know it even better. No one could honestly say that spending a week at a beach resort there is enough to really know a place, so going back allows you to dig deeper if you choose to.

Pro: Going back again is less stressful and more certain

Another compelling argument, at least for some people, is that a bird in the hand is worth two in the bush. For many, the process of researching destinations and hotels is a stressful one, especially on a low budget, so there is always that chance of checking into a paid-for hotel to discover it’s a dump. If you go back to a place you’ve loved in the past, you know where everything is and there is no stress.

Pro: You can really relax the second time

This is something I’ve encountered myself a few times recently as I return to cities that I’ve visited before. The first time in each place I made sure to see all the checklist attractions and try the favorite foods and all of that, so the next time the pressure is off and I can do only the things I enjoy. Removing the pressure of sightseeing can be liberating.

Con: Life is short so see as much as you can

The best reason to keep trying new places is that the world is huge and we can never come close to “seeing it all” but that doesn’t mean you shouldn’t try. Imagine, for example, if you visited Philadelphia or Reno and loved it, so you didn’t even go to New York City or Las Vegas. The same could be true of Cancun or St. Maarten. For all you know, the next place you go is far better than the last one, and you’d never find out if you keep going to the same place.

Con: The same place will get boring before you know it

Some good friends of mine took their first Caribbean holiday to the Turks and Caicos and they loved it so much that they returned to the exact same resort the next two winters. I thought it was strange, but it was there vacation. However, on the third trip they both revealed they found the place boring. The first time was new and exciting, the second time was like seeing old friends, but by the third time it felt like watching a rerun. They spent over US$10,000 on that trip, so it’s a shame they didn’t get what they hoped out of it.