The Family Trips You Should be Booking Now

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This time of the year often fades into a bit of a blur for me. We are passed the distinct winter holidays, but here in early-ish February, we aren’t yet to the spring holidays or summer break. We are just in the middle of one. big. dreary. chilly. blurry. day. I think this is when the winter blues could easily set in as life is a busy, mundane, cold, damp, whirlwind with some nasty winter illness sprinkled in here and there for good measure.


Book a flight out of dreary old February

Now that we know what time of year we are in, let’s talk about what time of year we should be focusing our miles on right now. If you are the award travel booker for your family, now in dreary old February is when you need to be seriously looking at the 2018 – 2019 winter break schedule as the booking window on most of the major airlines now goes through early January 2019. The exceptions are of course those airlines who don’t open their schedules roughly 11 months out, but for United, American, Delta, etc. you can get to booking…or at least looking.

As you probably know by now, not all award seats are magically loaded at 12:01 AM on the day the booking window opens, but that doesn’t mean you shouldn’t start looking as soon as possible. Sometimes the award flights you want are there as soon as the flights are loaded, and I’ve found that when it comes to peak school break travel times, waiting to book family travel rarely pays off.

Whether you want to head to the mountains, the beach, or just to grandma’s house, I highly recommend spending a few minutes today looking at award availability to see if you can go ahead and lock in next year’s winter holiday flights now.

Holiday festivities at the St. Regis AspenWhile you are at it, I also recommend checking out hotels for next winter break, too. Sometimes you can secure award hotel reservations even further out than airline seats. Hyatt allows you to book about 13 months in advance and Starwood goes up to 18 months out. This means I am actually about to book our Spring Break 2019 hotel reservation using Hyatt points since Texas Spring Break Week is traditionally in mid-March, which is closing in on 13 months away.

If you aren’t used to planning travel this far in advance I totally understand it is a big mental adjustment, but when you need to book multiple seats during peak travel times, the earlier you can start looking the better.

Do you have your winter 2018 – 2019 holiday travels booked or outlined? Where is your family heading?

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  1. We have a family trip to Orlando (2 days Disney/2 days Universal) in October.

    Hubby and I are headed to Park Hyatt St. Kitts the day after Thanksgiving. (Yay!)

    Kids vetoed travel over
    Christmas this year. ☹️

    Starting to look at our January couples trip, and family Spring Break is on the horizon.

  2. Been looking for WAS to HNL flights for Christmas break – Do award flights even exist?!? I swear, every airline seems to want an arm AND a leg.

  3. I’ve already secured a hotel with points in Puntacana for Holiday 2018, but flights are running $700 from DC area!!?? Ouch. Do I book now before they go higher or wait for Spirit/JetBlue/Southwest flights to open up? Unfortunately, we do not have enough miles at the moment…the award mile rates are high too!

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