Saving Money vs. Jumping at a Vacation Deal

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How do you normally travel?  Do you plan it out far in advance and search for the best airfare deals first?  Or the best hotel deals first?

I’m in a bit of a predicament right now (albeit a good one!)

For the next 12 days, TripAlertz has this deal for 1 week’s worth of hotel stays for only $395… and that’s not per person.  There are a lot of countries to choose from, but my main focus is Hawaii.  Right now there are a few resorts in Kauai that offer 2 bedroom apartments and can house up to 6 people (if friends decide to join us.  That would up the savings even further.)  Justin and I have enough points for 5 round trip tickets to Hawaii but at the moment we don’t have any for hotel stays.  If we were to buy this and go alone, we’d only pay less than $60 per night for 7 nights.  This seems like the perfect opportunity to book a quick 1-week vacation to Hawaii!

But… there are a few caveats.

  1. Justin won’t have enough vacation time until next year.
  2. The TripAlertz deal can only be used within 1 year of purchase.  Therefore, with Justin’s vacation limitations our time to travel will be between January, 2013 up to August, 2013.
  3. You can only reserve the TripAlertz deal within a 60 day travel window.Ex:  If you are planning to travel on February 1, 2013, you will not be able to view available hotels until December 3, 2012.”  If I didn’t have the flights covered, I wouldn’t take this deal.  Buying a flight only 2 months out would most likely end up with an expensive fare.
  4. Our airlines award miles can only fly Alaska Airlines, and I’ll have to reserve flights less than 2 months out to match the hotel stay.
  5. We’re already going to Fiji for 2 weeks in May, 2013.
  6. Even though this will be an inexpensive vacation, we’ll be spending a lot of money on food, excursions, shopping and car rental (on top of what we’ll spend in Fiji.)

My main concern is #6.  On top of Fiji vacation spending, we’d be spending MORE money that we could be saving for the future.  I’m also a little concerned about hotel availability matching up with my airfare rewards too.  I just checked hotel availability from now until September and there seems to be a lot of hotel locations available.  If I were to book, I’d shoot for January or February… which won’t be a busy season compared to summer time.  So potentially, January would be in Hawaii… and May will be Fiji.  A 4 month spread.

Its funny that one of my main priorities in life right now is going on vacation, yet I’m concerned that I’m taking TOO MUCH vacation (and spending the money that comes with it).  I really wish I could take this trip during the 2nd half of 2013 to spread it out a little bit more.

In Hawaii we normally pay around $100 or so for a place to sleep.  Over a 7 night stay, this would save us $280 in hotel costs in comparison.  Is saving an extra $40/night worth it?  Or should I just wait until the end of 2013 for another trip to Hawaii?

This is all a matter of timing, really.

What do you think I should do?