Taking Your Dream Vacation

Years ago, a friend called me after returning from a life-changing event called a vacation.

“Scott, do yourself a favor and book passage on a cruise,” he told me. “It’s nothing short of amazing! The ship takes you to different ports where you can shop and gamble. And on board they have art auctions and 24-hour buffets. They will even deliver a tuxedo in your size to your stateroom so you can dress up and have dinner with the ship’s captain!”

That’s not a dream vacation in my book. It’s a nightmare in which I try desperately to wake myself screaming.

Obviously, there is not a single “dream” vacation, because we all enjoy different things. However, if you plan to take something that resembles your version of a “dream” vacation, I suggest–

3 TIPS to a rewarding, memorable vacation!

Oh, and in case this doesn’t jump out at you, the same tips apply to building happiness the other 50 weeks of the year.

1. Have realistic expectations.

Don’t get sucked into the hype. Just because the ads for Vegas promise that you can go “From rags to riches” and “What happens in Vegas, stays in Vegas,” be skeptical. Those ads were paid for by the 99% of people who subsidize Vegas by losing vast amounts of money. And that disease you picked up in Vegas? It doesn’t stay in Vegas. It comes home with you.

There’s nothing wrong with wanting to see a pod of whales on vacation. But the only way you can ensure you’ll see one is to watch a video called “A Pod of Whales.” Seeing a pod of whales falls outside of your control, so don’t go in expecting a pod. Instead, hope for maybe a single whale…or maybe just an unusually long fish. And then be happy for it!

And for the love of Pete, don’t go on vacation with your family expecting that you’ll get closer. Yes, you will experience extended periods of forced proximity, but that’s not the same as closeness. If you enjoy your family, taking a vacation with them will deepen your love and appreciation for each other; however, if you can’t stand your family, you’ll just be finding a new, more expensive location where you can hate them. Don’t expect the nature of your relationships to change with the zip code.

Expect nothing, appreciate everything. If you enter vacation with that mindset, you can find a reason to be grateful even when your plane has a mechanical problem that leaves you delayed at the gate–i.e., it didn’t have a mechanical problem in the air!

2. Set some goals.

No, I’m not trying to squeeze all spontaneity out of a vacation, but enter your time with some sort of stated goal. It can be as simple as “I plan to go to bed when I’m tired and wake up when I wake up.” That’s a great goal, especially if your day-to-day doesn’t give you the option to sleep until you wake up on your own. And by stating that goal, you won’t feel guilty for “sleeping the week away.” It was a goal, and you nailed it!

When we took some time off this Summer in southern Oregon, my wife and I planned to hike one of three mountains. That was our goal. We ended up hiking two of three, and we will hit the next one when we return. We left with a sense of accomplishment.

I’ve had more than one person tell me that the greatest joy of writing down goals is the satisfaction of crossing them off! Try it. Set a few goals the next time you take time off. And see how much joy you get from checking them off.

3. Invest in new experiences.

One 2014 British study reported that most English vacationers eschew trying new activities, testing out different hotels, tasting new cuisines or even touching their lips to an unfamiliar ale. Instead of risking disappointment, many go to the same vacation spot year after year.

How about you? Do you tend to go to the same restaurant, sit in the same seat, ask for the same server, and order the same meal when you go out to eat? If you’re like most people, you do. You tell yourself that you do it because you’re loyal. But in reality, we all tend to find what we like and then stick with it, because it’s safe and predictable.

Your dream vacation requires you to invest in new experiences. I still remember vividly getting up on water skis for the first time when I was thirteen years old in a small lake in Indiana. I remember my first fish taco in Mexico and the freshness of something caught and cooked before my eyes. I remember the first time sipping house wine in Rome that was cheaper–and better–than anything I had tasted. I remember the first time I rented a motorcycle in Jamaica and toured the beautiful countryside far away from the resort. I remember the first time I drove a Jeep over real mountain trails, trails that turned out to be snowmobile trails that were so dangerous and snow-covered that the place I rented the Jeep from yelled at me for twenty minutes when I told them where I’d been.

You don’t get those kind of memories from staying in a safe, predictable rut. No one cares that the McDonald’s in Paris didn’t have sesame seeds on their buns. The way to return with a story worth recalling is to go bold and order escargots, confit de canard, and mille feuilles. Lasting memories bloom from trying new things.


So how can you take a vacation today, even if you’re at work all day?


Leave a Reply

Your email address will not be published. Required fields are marked *