When to book online travel deals

 In Travel Tips

Every single day an email hits my inbox tempting me to pack my bags and hop on a plane. No joke.

Where will it be today– Fort Lauderdale, Iceland, Costa Rica, Beijing, San Francisco or New York? There are flight deals happening every day, vacation bundles being thrown in my face and hotels offering discounts that can’t be matched– but for one day only. How do I decide which ones to pounce on and which to pass me by? Well my bank account sure helps, but I do have a mental process I go through.

  1. Do I actually want to go there? This is a no brainer, but really, if you don’t want to go to Cleveland or Dubai, you are better off saving that money to go somewhere you really do want to go.
  2. Is it on my “list”? Yes, I have a mental list of places I am dying to go. Argentina and Greece are just two of them. Oddly enough these two places have popped up in my deal alerts and I haven’t book, which brings me to my next question.
  3. Is it actually a good deal? Often times I have a few destinations on my radar. I generally know what the prices look like to get there. If I see a deal come up I can mentally calculate if it will actually save me money and be worth the trip or not. If you don’t have this info in your head, just go to sites like Expedia or Skyscanner.com and do a quick flight and/or hotel search. If you won’t be saving at least 30% then it really isn’t a great deal unless you are already heading that way.
  4. Is it safe? Obviously no one wants to bring their kids to a war-torn country. I tend to go in the opposite direction of strife and weapons.
  5. Can we take the kids? Again, this seems like a no brainer, but it is actually harder than it seems. If you are going to a higher altitude, are your children old enough to go beyond 9,000 feet? Will you and your children need special vaccinations or have to take anti-malarial pills in order to travel to the destinationAnother thing to consider is will you be able to do all you want to do in that destination with your kids? My husband and I struggle a lot with whether to bring our kids with us to Tokyo. It is not that it isn’t kid friendly; they have Tokyo Disney and toyshops that make grown men (i.e. my husband) swoon after all. No, it is because we want to experience the late night culture and abundant array of food. Could we do it with the kids? Sure! But do we want to? That is the harder question.
  6. Can my husband go? There have been more than a few times that I have jumped on a deal knowing my husband couldn’t come. He works long hours at certain points in his projects and it’s easier for the boys and I to just run off for a week instead of missing him. However, every single trip or deal I look at I do talk to my husband first to see if he can come. Sometimes this means I miss a deal while he ponders it, but we haven’t missed anything that was crucial.
  7. Is there any money? Obviously without money you can’t really book plane tickets or a package you see pop up online. We have a travel budget that we regularly add to. From this budget I know if a deal looks feasible or not. I’ve had to skip many because our coffers were running low. The good news is that more deals will pop up.


When a package deal to Iceland showed up in October, I looked at my husband and told him I was booking ASAP. I knew we had the money and he could take the time off to make a quick trip to realize our dream of seeing the Northern Lights. The same could not be true about a flight deal to Peru that came up last year.

For about $400 each we could fly from Seattle to Peru and be staring at Manchu Picchu over Thanksgiving. However, the altitude was an issue for the kids. They were so little and would have had to be carried through most of this world heritage sight. In the end we said goodbye to the deal, which broke my heart, but knew we wanted to be able to fully experience the country with our kids, which maybe we could have, but with an infant and toddler we just weren’t ready to do it.

Not every deal will be right for you or your family. Just like booking any vacation, you need to stop and think. If it is your dream to see Iguazu Falls in Argentina, but your bank account is looking low and the deal is only 10-20% off than maybe this just isn’t your time to go. There will be other opportunities. I promise. New price breaks are popping up every day.

Want to know where to find the best travel deals? Read our top list of travel deal sites to subscribe to this year. 

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Showing 6 comments
  • Lauren Supina

    Iceland sounds great! we have been watching fares there as well. Took my two boys to Peru last year and they loved it! (6 & 7) couldn’t hike the trail – which I’ve done in the past – but taking the train was amazing. highly recommend Peru. great to connect with you.

  • Sally@Toddlers on Tour

    So true Keryn.

    I always have an idea of

  • wandering educators

    Great tips, Keryn – especially about going where you want to go! 🙂

  • Colleen Lanin

    You forgot, “Can I afford it?” Even if it’s a great deal, if it’s not in my budget I have to pass! LOVE your site’s new header BTW!

  • Murissa

    All great tips. I am establishing my travel fund, which has recently been depleted as of late. But I am looking forward to building it back up!
    March will be my first trip on my way to Boston for the WITS conference – will you be there?

    Love the new look of your site by the way!

    • Keryn Means

      Sadly can’t make it Murissa. Have a great time though!

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