Y’all, I just booked my first trip around an actual school calendar. I know it’s a serious rite of passage for a traveling family, so happy to have checked that one off the list. We have been operating largely on a school calendar for a few years thanks to my daughter’s pre-school, but I didn’t give a fee-fi-fo-fum about her missing a day of pre-school here and there. I care a bit more about her missing a day of real Kindergarten, though I know she will never win the perfect attendance award there either. Sorry, kid you just gotta shoot for getting awards based on actual grades, or test scores, or whatever they recognize kids for these days.
Planning way ahead for family travel may make you feel like a crazy person, but it makes your points stretch further and allows you to maximize school breaks much more effectively. Here is what we did today and why.
Plan Far in Advance for Hotel Room Availability on Popular Dates:
I’ve been wanting to take my 4.5 year old to Mickey’s Not So Scary Halloween Party at Disney World for a while, but have been waiting until the “right” age to do so. If you aren’t familiar, they do the event on select nights in September and October with a (not so scary) Halloween theme, and it is very popular and looks super fun for the little ones. I strongly considered taking her this October since I think almost five is a good age for the festivities, but a combination of no availability at the Swan or Dolphin on SPG points + an already busy travel schedule in October killed that plan before it got off the ground. Since this is a once-a-year type of event my mind naturally jumped to October 2015 as a good time to go….I know, crazy person planning syndrome.
October 2015 is too far out to make airline reservations, but it isn’t too far to book hotel nights with some programs like Starwood Preferred Guest (and Club Carlson for that matter). You can make reservations up to 18 months out via Starwood, which meant that I could lock in some nights at the Walt Disney World Swan hotel with two queen beds on Disney property for 10,000 SPG points per night now. SPG offers a standard room on points if it is for sale with cash. Remember that all the October 2014 dates I looked at there were already full, so I was like a kid in a candy store with October 2015 wide open, even on weekends. Paid rates were close to $350/night with taxes (and I expect them to stay close to that number for “Not So Scary” nights), so 10,000 points per night was an easy call at around a 3.5 cent per point return. There are much cheaper places to stay in Orlando, but this property is on Disney sacred soil and thus has many of the associated perks of staying on-property. Being able to use points and stay in the middle of the action is pretty great for a quick weekend Disney trip. My runner-up choice when visiting Disney World from a hotel points perspective is the nearby Hyatt Grand Cypress, though I would love to try the Bay Lake Towers right next to the Magic Kingdom if I accidentally tripped over an extra pile of money or Disney Vacation Club points.
Look for Long Weekends on School Holidays:
Another part of this process was to look at local school calendars from the last couple of years and find a weekend in October that traditionally has a built-in Friday off in order to maximize the weekend getaway without unnecessarily missing school just to trick-or-treat with Mickey. I found a Friday in October that usually at least has early release at the end of the first nine week grading period and let that be our go-date. The school calendar isn’t yet finalized for the 2015-2016 school year, so it’s totally possible I am off with my estimated date, but that’s no big deal because my hotel reservations are changeable until a week before anyway. I have 80-90% confidence that the Friday we picked will be the correct school holiday based on previous calendars, and can see myself becoming obsessed with school calendars in the immediate future.
Since the overwhelming majority of family travelers are looking to travel during the same school breaks you really have to plan as far in advance as you can to both avoid the kids missing more school than they need to, and have your pick of good availability when using miles and points. Planning at the very last minute can also result in success with availability that opens up, but that’s not something I would personally bank on regularly for family trips.
How do you maximize school breaks while utilizing miles and points? I know I’m not the only one with Crazy Person Planning Syndrome!