“I am generally careful with money but when I go on vacation I like to live large.

Unfortunately, I end up spending more than I can really afford. Can you offer any tips for saving money without depriving myself of fun?”


You want to remember your vacation forever… but not because youʼre paying it off forever.

Nothing is better than a good vacation to recharge your batteries, broaden your experience and make beautiful memories. But automatically switching into extravagant mode “because hey, Iʼm on vacation,” is a big mistake. You can have just as fantastic a trip while remaining your frugal self.


Start with a dollar amount, not a destination.

When planning a vacation, I like to start with a number. Picking a budget before Iʼve even picked a place is surprisingly liberating. Setting strict economic boundaries will set you free—from agonizing over endless options (“Should I upgrade to an exit row seat?” “4- or 5-star hotel?” ad infinitum). By settling on $1,000, say, as your departure point, the decision-making process suddenly becomes more efficient, like with a dating website when you narrow your romantic options down to a specific age range and distance.


So you’ve picked a number—what next?

  • Sign up for email alerts from travel websites that will find you the best flight and vacation deals within your stated budget.
  • Use Airbnb instead of a hotel. By renting someone’s apartment instead of a generic hotel room, you’ll not only save big but also have a more interesting experience. For stays longer than a week, I recommend VRBO.com as an alternative to Airbnb. I have used the site to rent out an entire house for a family get-together, and it was so much more enjoyable (and cheaper) than separate hotel rooms.
  • Don’t wait too long to use your reward points. Increasingly, airlines are setting expiration dates for redeeming air miles and other points. I’ve spoken to a lot of people who saved their points for some special occasion, only to find they were no longer valid. Use them or (eventually) lose them!
  • Booking your flight no less than 30 days before your departure date is the general rule. But if you are utterly flexible, you may prefer to wait for last-minute deals from companies eager to get rid of excess inventory. Some websites are dedicated to offering bargain-priced hotel rooms, flights and packages at very short notice. There is something exciting about going to an unexpected city and hotel at a moment’s notice. If you’re in the early stages of your retirement, in great health and have a sense of adventure, this wait-and-see option can really work in your favor.
  • Use a price comparison website like Hipmunk.com to search for flights; no one airline has the best prices all of the time. Be willing to fly on an unpopular day like Wednesday and at less convenient times of the day to snag rock-bottom prices.


When attempting to get the best deals, it’s important to consider the trade-offs you’ll be making and the possible wear and tear on your body. If you become too fixated on cost savings, you might overlook the cost to your overall well-being. A grueling journey to and from your weekend retreat, with a 3-hour layover en route, may leave you exhausted for the entire trip. If you’re not a morning person, don’t book that 6 a.m. flight, however alluring the price. It may be worth paying an extra $50