Planning Summer Travel

This seems rather strange, perhaps, but Sarah and I have our summer plans more or less penciled in through 2015.

That’s right, 2015

This summer, we’re going to Seattle. The following summer is a trip to New Orleans with my family. The summer after that will feature a trip to Boston, with the summer after that featuring some extensive national park camping. The summer after that? Disneyworld.

We’ve even started talking about subsequent vacations, including trips to Norway, Japan, and France by the end of the decade (we want our children to be older before traveling internationally).

Why plan ahead so much, you ask?

It’s simple. Planning ahead on your summer vacations is an enormous money saver. Sure, maybe we’re going over the top a little bit with the advance planning, but having a firm grip on where you’re going at least a year in advance can save a huge amount of money.

Here are some of the reasons such advance planning really helps.

The day of the week you travel on really matters. If you watch airline ticket prices, you’ll quickly see that not all days are created equal. Tickets for flights on Wednesdays and Saturdays are much cheaper than tickets for Mondays or Fridays.

This, of course, means that planning the days you travel in advance can save you a lot of money, and the further in advance that you plan it, the easier it becomes to get the needed vacation time at work and so on.

You have more time to shop around for better rates on plane tickets, lodging, meals, and any other events. I’m not going to get into the mountain of travel sites out there, but suffice it to say that shopping around for tickets can save you quite a lot of money. The further in advance you’ve planned for a vacation, the more time you have to shop for such things.

The more time in advance you have, the more you can focus on banking frequent flyer miles. There are lots of ordinary things you can do that will help you to bank frequent flyer miles, and the more miles you have banked, the fewer tickets you’re going to be buying. Considering that our family’s travel in the air requires five tickets, that’s a fair chunk of change. Thus, for us, sites like TravelHacking actually pay off.

You have plenty of time to make (or re-establish) connections in the city you’re traveling to. Having people in the area means an inside track on things to do, places to see, bargains, lodging, food, and countless other expenses for travel. If you know long in advance that you’re coming to the area, start making contacts and re-establishing old ones. For me, this is easy – I know readers of The Simple Dollar in most of these areas, so I just send them an email. For you, look for any groups that you might be involved in. Put out a notice on Facebook. You might be surprised who pops up.

You have plenty of time to learn about the area you’re traveling to. This doesn’t mean filling your schedule with more stuff to do than you could ever possibly accomplish. It means investigating the area you’re traveling to thoroughly so that you can truly find the best experiences for your dollar and time.

In my own years, I’ve found that it’s rarely the “name” attractions that are worthwhile. My best memories from virtually every vacation I’ve taken have not been the expensive attractions, but the small free things, like walking past Westminster Abbey and Parliament with my wife while in London, her hand in mine, just absorbing the history of the area, or sitting next to my sister-in-law in a park in Canada, taking our shoes and socks off, and splashing our feet in some freezing water.

There is some serendipity in these moments, but the more time you give yourself in advance of leaving, the more likely you are to find things and events that are going to provide a very powerful media for such serendipity to grow in.

But what about spontaneity? Yes, it can be a lot of fun to just jump in the car or on a plane and see what happens. The problem with that, however, is that it tends to be expensive. You’ll often wind up in suboptimal situations. If you’re planning for that, great, but you can have just as much fun for a lot less if you put in some legwork in advance. A second problem is that it’s extremely difficult to go completely unstructured with young children, because while single me would have happily slept in a sleeping bag in a state park, I wouldn’t do that with a one year old and a three year old in tow.

However you decide to travel, good luck on making it cheap and fun!

Trent Hamm

Founder & Columnist

Trent Hamm founded The Simple Dollar in 2006 and still writes a daily column on personal finance. He’s the author of three books published by Simon & Schuster and Financial Times Press, has contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and his financial advice has been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.