
Most people go on vacation with expectations of a non-stop extravaganza or with the hopes of an interruption-free solitude. That’s what I call setting yourself up for failure. Neither of those two is going to happen. We both know it. Whether you are envisioning a week of beach lounging and Pina Coladas or a week on the slopes around Grand Teton National Park and plenty of fresh powder, there are a few things you need to make sure to do to set yourself up for a successful vacation. The following tips should show you how to go about planning your vacation most effectively without risking disappointment.

Photo by mode via Flickr
Hands down, budgeting will make your trip go much more smoother than otherwise. A few useful basic budgeting tips to keep in mind are:
Each step relies on the preceding step. It’s like a deck of cards — if one card gets pulled, the rest might come crashing down.
Budgeting will enable you to plan your vacation without rose-colored glasses. If you have the numbers staring you in the face, you can’t fake yourself out that the Waldorf is within your budget… you might have to settle for the Holiday Inn!
It’s funny how much of personal finance comes back to budgeting. It’s the tired old mantra, “Spend less than you earn!”
Two of the most expensive parts of vacation are the transportation and the housing accommodations. So naturally, you should try and save money in those areas first.
In order to make your job easier there are a plethora of online travel aggregators to help you find cheap airfare and hotel. Whether your vacation is domestic or international, these sites offer you a ton of options. You can search by day and location and opt to allow it a certain degree of freedom in day variations to find cheaper prices. You can search for just the flight on all of them, and some even allow you to search for vacation packages! These would include the airfare and hotel with the option of including a rental car.
Another area I try to focus on is critical reading. What exactly does critical reading have to do with saving money? Well, I think reviews are pretty cryptic so I try my hardest to decipher vacation reviews that I read on travel sites. Expectations are everything and I have found 5-star hotels that sucked and 3-star hotels that were awesome. If you read the review on a 3rd world hotel that mentions their unpowerful toilets, the person obviously had an unreasonable expectation of an “Un-American toilet.” Hence, their review is crap.
For the people whose family consists of a furry critter, pets are another expensive concern to think about. If you are gone for 5 days and have to pay for boarding, it could cost you an additional $300 on top of your trip. However, if you follow the tips on reducing pet care costs and set up a care network, there would be no cost associated with this.
Two psychologists named Boven and Gilovich wrote a paper in 2003 called “To Do or to Have? That Is the Question.” The result of the study was that they found out people wind up appreciating their experiences over their possessions in the long term. Interestingly enough, the data appears to show that experiences matter more as income levels rise. There are other interesting causalities, click and read through the data!
More data suggests that people often stick to the norm even if they think trying new things would make them happier. So here you have people who know experiences matter more and who want to try things but wind up sticking to the norm.
What should people do? Take more experimental vacations!
In an essence, all of this advice boils down to a few things:
On that note, I am back to planning my vacation. It’ll be on the first week of November! I’ve been looking at two polar opposites: Montreal (Brrr) and Costa Rica!

All posts by MLR (Staff Writer)
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I also think that being open to new experiences is a good idea. Meaning that even if things don’t quite turn out the way you’d envisioned, maybe what actually happened is still enjoyable.
@ Jackie –
Expectations are often times will make or break your vacation. I’ve learned my lesson from the few vacations that were “terrible.”
Live and learn, right!
Hey MLR! I can’t really debate you on this topic here as we did on your site and mine
I gotta say, the past 12 months have been staycation time! Discovering San Francisco and the surrounding Bay Area has been wonderful. Going to watch the President’s Cup golf tournament was sweet, and the Blue Angels flew by that weekend too.
As winter comes, it’s all about enjoying the snow in Squaw, Lake Tahoe. In fact, I’m here right now writing this entry!
Discover your local city. I’m sure there’s so much to learn!