A cheap vacation is a flexible one

The fewer things you lock into stone in your vacation planning, the more opportunity you have to dig into better values when they come up. For maximum flexibility, schedule more time off than you absolutely need, if possible. 

Kathy Willens/AP/File
This 2010 file photo shows Coopers Beach in Southampton, NY. Hamm recommends taking more time off than you need for vacation travel. That way, it's easier to take advantages on deals on flights, lodgings, and activities.

During the last few years of my previous job, whenever Sarah and I began to plan a vacation, I would request time off in a block that was significantly larger than the length of the vacation we were planning.

Sometimes, I’d wind up with several days off before the vacation. Other times, I’d wind up with several days off after the vacation.

Why would I do this? I had to take time off pretty far in advance in order to get it off, but I didn’t want to lose the flexibility of vacation planning opportunities, so I’d schedule more than enough time off so that I could be flexible within that larger time frame.

This isn’t just a principle to apply to time off. The fewer things you lock into stone with regards to your vacation, the more opportunity you have to dig into better values when they come up.

For example, let’s look at flights. If you absolutely have to fly out on a Friday evening and then absolutely have to fly back nine days later on Sunday evening, you’re going to pay out the nose for those flights. Now, let’s say you have some more flexibility there and decide instead to have one of your flights on Wednesday instead of Friday or Sunday, you’re going to save a lot of money on your flight.

The same thing happens when you look at activities during your vacation. The more flexible you are with those activities, the less your trip is going to cost you.

Our usual plan is to come up with a large list of potential activities that we might want to engage in on our trip. We make a list that’s far longer than what we could possibly fit into a vacation.

From that list, we seek out bargains for each item on that list. Which ones are cheap on particular days? On which day does that baseball team have a “bobblehead night”? On which day does the museum have a “kids are free” day?

We’ll slot in activities on particular days, but we still don’t jump on tickets unless (a) there’s a genuine danger of a sellout or (b) we find an exceptional deal (50% off or more) that comes from buying right now.

Often, we’ll start our vacation with very few things firmly slotted in place.

Then, when we arrive, we’ll ask around for discounts. We’ll ask the hotel concierge if they have any extra discounts on the things we’re thinking about doing. We’ll read some local newspapers and local brochures.

Because so much of our vacation is flexible, if we find an activity is cheaper on a particular day, we can easily do it on that particular “cheap” day.

In the end, we find ourselves with a pretty low-cost vacation that ends up filled with things we enjoyed as a family. That’s a winning trip.

This post is part of a yearlong series called “365 Ways to Live Cheap (Revisited),” in which I’m revisiting the entries from my book “365 Ways to Live Cheap,” which is available at Amazon and at bookstores everywhere. 

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