How to Make the Most of Your Money While on Vacation

Magazine Contributor
3 min read

This story appears in the August 2014 issue of . Subscribe »

Like many small-business owners, I'm a workaholic. My girlfriend chides me for my tendency to do "just one more thing" in the office at the end of almost every day. And it used to be impossible for me to justify a vacation. It wasn't just the time away from work that worried me; it was the cost--every dollar I spent on travel represented more work I'd have to hustle up to pay for it.

Turns out I had it all wrong. Research has shown that people are most satisfied when they spend on experiences instead of things, and spending on vacation is one of the best ways to buy this kind of happiness--and keep your sanity.

Why else would a company like Clif Bar give its employees an eight-week paid sabbatical after every seven years on the job? For starters, it's a fantastic recruiting and retention tool. And it allows employees to decompress, then return to work in a clear mental state, one that is conducive to coming up with new ideas to make the company better.

Why would you or I think we're immune to these vacation benefits simply because we own businesses? News flash: What's good for employees' productivity is good for us, too. In the last couple of years, I've made vacations a priority, and guess what--my business doesn't collapse because I take off for a week.

Vacations don't have to be expensive--just approach them like you would any business or personal expense in which you seek to maximize value. In his book How to Travel the World on $50 a Day: Travel Cheaper, Longer, Smarter, Matt Kepnes argues that with creativity and careful planning, you can get out there for much less than you'd expect. "If you travel like you live at home, travel suddenly becomes a lot more affordable," Kepnes says.

To make the most of your money, focus on the "big three" vacation expenses:

  • Lodging. Kepnes recommends using to find family-size accommodations for less than you'd pay for a hotel. If you must stay at a hotel, use or to find the best prices--but do a search for "winning hotel bids" before you make an offer, so you know you're not bidding too much.
  • Transportation. A round-trip flight to visit my girlfriend's family in Sacramento, Calif., usually costs about $280 per person, but I use to alert me to fares as low as $108. When I must travel on a specific date, I use to find the best prices.
  • Food and entertainment. If you're traveling in the U.S. or Canada, order a copy of the Entertainment coupon book for your destination city at It's packed with coupons from local restaurants, theaters, cultural attractions, amusement parks and even hotels.

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