For the past 7 or 8 years I’ve gone shopping on Jan 1, at Dillard’s, and I usually buy the majority of my clothes for the year during that sale.

I don’t think I’ve ever walked out of Dillard’s from a Jan 1 sale with less than 15 items of clothing (usually 20 or 25), and I don’t think I’ve ever paid more than an average of $20 per item that would normally have cost $60 to $100.

Even better, because they have so many name-brands to choose from, I can be 10 times more discerning than any other time of the year when shopping for clothing.

  • $60 Levi’s jeans for $20? Not when I can get $150 Armanis for $28
  • Dress shirts I buy range from $12 to $26 and I only buy brands people don’t bat an eye at paying $50 to $120 for any other day of the year.
  • I rarely even bother giving my kids clothes for Christmas any more because I know I won’t find a better deal than what I find for them on Jan 1.
  • I’m going on vacation to Turks & Caicos in a couple weeks and was so mad when I realized that the sale applies to sunglasses/watches too! (I rarely leave the clothing department because I’m so exhausted by the end of my shopping spree. Next year, I’m starting in sunglasses. They apparently get cleaned out within 30 minutes of store-opening.)

As I was walking out of the store feeling like Santa with a bag of goodies bigger than me slung over my shoulder, I realized something…

Finding a good deal on vacations is a lot like shopping.  

Sure, you can find flights to Cabo like everyone else does, and you can pay what everyone thinks is a good price. Or…

  • If you can be flexible on where you want to go,
    • you could find flights and an all-inclusive resort in Cancun for the exact same price.
    • you could fly to Belize or Aruba and stay for 7 nights for even less than a flight alone to cabo.
    • Depending on how long you’ve got for a vacation, you could spend even less for flights and lodging for a couple weeks in Europe or Asia.
  • Much like buying summer clothes during winter sales, if you plan vacation time around when you find an amazing deal (vs hoping to find an amazing deal between July 1 and July 10) – you can save a ton. (That only works if you plan ahead though.)
  • Decide to try a new credit card once a year in return for 50,000 or 100,000 frequent flyer points, and the game changes even more.

I don’t care if you use my premium email alert service, or a mashup of my free service and a dozen others …

Make the following 3 things a priority for your next vacation, and I promise — you’ll save more on your next vacation than you ever thought possible.

  1. Don’t plan trips around vacation time… Plan ahead and schedule vacation time around trips that are too good not to go on.
  2. Plan 6 to 12 months ahead
  3. Be flexible on where you’re willing to go.

(Extra credit): Get a new credit card, and save the bonus miles for a rainy day. (Not 5, not 10. Just throw your old card in a drawer (after paying off the balance) and get a new card with a 40,000 to 100,000 point signup bonus. You never know when those miles will come in handy, but it only works if you plan ahead. (And you know what they say about planting a tree…)