Plan the Trip of Your Dreams

Posted On July 8, 2018

Well, provided your dreams are reasonable and you’re flexible. I love to travel, and I’m not rich. You, too? Let’s talk.


Six years ago, we took our three children to Italy. Never in a million years did we think that would be possible. Three things made it a reality: an abundance of painstakingly hoarded frequent flyer miles, a free place to stay (in other words, luck), and a good travel agent. This summer, having rebuilt the airline miles bank, we’re going to France, albeit without the free place to stay. Here’s how we do it.

First, we adjust our expectations for how we get there. When you use frequent flyer miles, you don’t always get your choice of flights. (Spoiler alert: You never do.) This summer, two of our sons are flying separately from us and will have to go through several cities and change airports in London. I was worried about it, but they’re 17 and 20, so if they don’t make it, then we’ll know what we’re dealing with. Not everyone is flying in on the exact day we wanted, but so be it. Those flights are free!

Sign up for a credit card that gives you miles for every dollar you spend and charge everything. Just make sure you pay it off every month or your vacation fund will go to the interest. It can take years to build up enough for a family trip, but it’s worth it. Try to get a card with a big sign-up bonus.

If we’re traveling somewhere less than ten hours away, we usually drive. Disney World is a lot less expensive when you cram five people into the car, instead of shelling out for five plane tickets, and what’s a few hours of driving when you get to hang with Donald Duck on the other end? Need a bigger car to fit your whole family? Renting one is probably still less than flying.

Second, we work hard to find free or less expensive accommodations. Having a friend who lives in Italy helped with that trip, but that technique isn’t guaranteed. But have you ever had someone offer to let you come stay? Do it! Assume they mean it, or they wouldn’t ask. Barring that kind of luck, try Airbnb, VRBO, or any online service offering short-term rentals. Staying in an apartment or house is usually a lot less expensive than a hotel, and since you’ll have a kitchen to make meals, you’ll save a lot on food.

Our third secret weapon is our travel agent. You might assume working with an expert adds to your cost. Au contraire. A travel agent is usually paid by airlines, hotels, and resorts, not by you. A knowledgeable pro saves you money and misery. If you want a room upgrade or your flight is canceled, and you need to be rebooked, an agent’s ongoing relationship with the resort or airline gets her foot in the door, and you won’t have to spend your vacation screaming on the phone.

A good travel agent can handle a budget. He or she should be able to offer a few choices that suit your needs or explain what’s reasonable in your price range and what you might have to give up. Agents can also save you from costly mistakes based on the area where you’re traveling. Mistakes cost money.

You can take the trip you want, if you plan way ahead. Last-minute trips are costly, but if you’re patient, you can travel the world. (Or at least the country or the state.)