Planning (WAY) Ahead to Maximize Points and School Breaks

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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.

Mickey Halloween Party

Mickey’s Not So Scary Halloween Party

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!



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  1. For our family we were open to missing school through middle school. Flying to Seattle during Sept to see the King Tut exhibit got her two days off 7th grade. Going to the Apostle Island Ice caves with her Grandpa gave her lifelong memories. I figured she will learn more than she will miss when its just a couple of days.

    • Stretching to travel, I’m sure it does get harder in middle school. I have no doubt we will miss some school days for trips, but I’d like to limit that when possible…especially for things that have zero educational value like Halloween with Mickey. Visiting family and experiencing more educationally valuable places would rank differently for me for sure. Ice caves with Grandpa sounds awesome!

  2. You are not the only one. I am a crazy advance planner. My son starts first grade this year and I am not only already planning 2015 travel, but 2016 as well. At least the dates and places so I can be ready to book the minute the window opens. That’s what you have to do! We used to always travel off-season, but with a kid you have to travel peak season with everybody else.

  3. Booked Tksgiving family travel to Brazil back in February. Got the lowest mileage redemption on Delta for 3 tickets and purchased mine at a very good price. All on the dates and flights I wanted. Kids have the Tksgiving week off at school so it makes the perfect timing to spend 10 days down there. Also, you can plan according to the school calendar on days that won’t make much difference if they miss classes. For example, the last week of school year is more about celebration, cleaning desks, etc… Final exams are already taken and summer is knocking in the door so not much to be missed if a day or two is needed to make vacation plans easier.

  4. My little one starts kindergarten this fall, so we have been planning around the upcoming school calendar for a few months now. Luckily, our district gives two days off for Veteran’s Day, so we will be headed to Disneyland in November!

    We’ve been enjoying traveling at off-peak times for these past few years… not looking forward to the next step. But I will certainly be willing to let her miss a few days of school here and there for something really important.

  5. Our 6yr old’s elementary school Principal was adamant that family vacations not be taken on school days… but seriously? what will a Kindergartener really miss in 5 days? So we pulled him in February for a week in Hawaii. His Kindergarten teacher thought nothing of it.

    I’m sure we will be pulling him for a family vacation when the timing and prices work out this year as well. I think until about 3rd grade, missing a week won’t cause great education harm!

    • I took a job substituting for a 1st grade teacher on maternity leave a couple of years ago. It was at a school located in a rich suburb. The kids were missing school all the time to go to places as far as Israel for up to two weeks in the school year. I think it’s fine, as long as you make sure your kid gets to read something every day (travel guides!!). I think that nothing gets closer to experiential learning than traveling.


  6. I have kids in high school, middle, and elementary. Our district publishes the calendar two years out, and I live and die by it. Our days of missing more than a day of school at a time are gone, and sports schedules put a further crimp in our travel, so I take advantage of every opportunity I can. I have our travel “schedule” planned out for at least the next 3 years!

  7. @Juno – The issue is not what your child will miss by taking school days off for vacation if they are working at grade level.

    The issue is the school district does not receive part of its funding for days your child is not in attendance. If your school district is as cash poor as every school district I worked, then you’ll begin to understand why there are constant fund raiser drives for classroom supplies.

    • @Ric I’ve never heard of this before (lack of funding for absent students), but after a quick Google search…Is it really an individual’s absence that costs the school funding..Or is it an average attendance over the course of the entire year for the whole school that will reduce funding if this average gets high enough?

      Either way, I guess taking kids out of school can hurt a school (it’s just a matter of degree) so maybe including a $20-40/day allowance to be given to the school/teacher for supplies would be a good thing to build into a trip’s budget.

      • Growing up with a family of teachers we have certainly been taught not to miss school for many reasons (including funding) unless you really need to. Being there around 10:30A I think gets you “counted” for attendance and funding purposes around here, but that said for us it will just come down to moderation. We’re not going to be talked out of missing some school, but we will do our best to not abuse that privilege either.

    • @Ric Thanks for the info. I never heard of that but will have to check in to that in our county. What about sick days.. Do they count against the school system?

  8. My parents pulled me out of school for a week every October until I was a Junior in High School. I used to get assignments for the week ahead of time. I would spend an hour or two every day working on my school work. I would go back to school normally a assignment or two ahead of them.

  9. Each school district is different, check their policies. My daughter’s school allows excused absences for up to 2 weeks for experiences that are deemed to have educational value. You fill out a form, list the things she will do, and submit it to the principal’s office. We actually had to do it this year because they added more than a week of makeup days due to excessive snow cancellations, which conflicted with our award flights that were booked ~10 months prior. This meant she would miss a few days of school. We simply listed several museums and cultural places that we were going to visit and the request was approved, no problem.

  10. My daughter’s school is pretty against missing days for travel, though I do plan on her missing the last couple of days of school next year for a family trip to Asia.

    Mommypoints, welcome to my world! I’ve booked hotels for Thanksgiving and Christmas week. In a few weeks we book our flights for next summer; right after I plan on booking hotels. The advance planning is crazy, but the rewards are so great, given how much airlines and hotels jack up prices the nanosecond school lets out.

    When I tell them I’m planning this far in advance my friends look at me like I’m crazy. But to me, paying out of pocket for air/hotel for a family is a a very steep price for spontaneity.

  11. Since school-aged kids limit travel to mostly peek travel times, it helps to think about the quirks of your local or regional school calendars compared to the rest of the country. Are there local holidays or other reasons that your school student is off when most of the country is in school. Some examples are Patriots Day/Evacuation Day, a Monday in Mid-April celebrated in New England, or Cesar Chavez Day (March 31) or Harvey Milk Day (May 22) in California. In NJ, there is a teacher convention every November that every school closed for. Even thinking about the regional differences in when school break for summer can help find less peek travel periods. Schools in much of the South and West have summer break late May to early August, while schools in the Northeast are out late June to as late as early September. That means students in the whole US, (and college students) are out of school – and their families are traveling – during all of July. Fewer in late May/early June and late August.

  12. Planning as early as possible and focusing on the shoulders of summer or local school closing days can help with finding available awards without pulling kids from school.

  13. Well enjoy taking those days off to travel while the are younger! We certainly did. The 10 day Thansgiving trips, extra long spring breaks, days tacked onto to teacher work days to add up to 8-9 days. But high school is a different world for us, especially because of sports and activites where the expectation is that no practice or event can be missed. Our daughter’s school ended June 25, but she is expected to be back for high school dance team practices by July 7! I am working on accepting that we will continue to have pay some flight cancellation penalties and I will be thinking much harder about exactly which miles I use for award flights in terms of the cancellation policies. Booking hotels way in advance, though, makes so much sense.

  14. Pulling them out of school when they are elementary age is not too much of an issue but as they get older, the schools usually frown upon it. It is hard to know in advance when exams schedules will fall and many teachers are pretty strict about letting kids take these tests early or late. I talk from experience. We used to take the our kids out of school each year around October for a cruise. We tried to plan it around a long weekend so that they only missed about two days of school. It got harder as they got older. Even if they get their assignments from their teacher, missing classroom time puts them behind. Third grade is tough. LOL! Really, middle school is tougher. Have fun while it lasts. Now I have one out of college and two in college so we are enjoying a little freedom to travel when they are gone. Adult time!

  15. I noticed that the Swan and Dolphin have a $23 resort fee. Does anyone know if that is assessed on award nights? Resort fee + car rental (because you can’t use Magical Express) + parking fee adds up quickly. I’m trying to decide whether or not to apply for the SPG Amex or not. Contrary to most miles/points people, I’m a big fan of staying at a Disney owned hotel. Swan/Dolphin is a great location and a nice escape from 24/7 Disney, but I like the overload of pixie dust while I’m at Disney. Yes…I’m a little crazy.

    I’m not surprised that there would be no availability at those hotels in October, especially if you are going over a weekend. Epcot’s Food & Wine festival that runs from late September to early November has become very popular and the hotels over by the entry to International Gateway are the best location for enjoying the festival.

  16. I am a faithful reader of your blog, and think you always have some valuable information. I did a reservation before United devalustion and is thinking to make change on the retun date. Does”Cancel without redposit trick” still work?? Since I have booked a business class back then , I am afraid if I change now I might have to use the new chart. Please advise.

  17. Not-so-scary party tickets do read at the turnstile as early as 4pm. Even though the tickets say 7pm….tried it myself at a 2013 party. The stage show was our favorite part. What are you guys going to be? I actually got my husband to dress up with us! Only in Disney!

  18. We have started homeschooling one of our 6 kids which does give much more flexibility, as we consider homeschooling some of the others.

    I definitely agree with you and the other commenters that said “Fe Fi Fo Fum and who cares” to missing school – I would say certainly through elementary school if not middle school.

    • @Points with a Crew, The school district I am most familiar has a policy that all such absences are unexcused and it is up to the teacher whether missed work can be made up for credit or not. Further, an accumulation of unexcused absences, when it reaches a certain point, gets reported as truancy, which means you’re getting the attention of the legal system. Check with your own local authorities before making a child miss a lot of school. (One or two days may not be a big deal.)

      Also I think there’s an equity issue that some may want to consider depending on your school context. Your kid has parents who have the wherewithal to zap her off to Paris, or Disney, or a cruise when they feel like it. Maybe the kid in the next seat has a single parent who is working multiple jobs just to try to put food on the table. Others may view it differently, but I think singling out your kid up as the super-privileged member of the class who always gets to miss school for fun trips may not always resonate well with other kids, their parents, and the school authorities.

  19. What about the parents? Obviously not applicable to SAHMs but if the majority of the office all want to travel at the same time, some folks are gonna hafta hold down the fort.

  20. I have been planning way ahead for years, as this is the best way to secure award seats for my family of 4 during popular family travel weeks in February and April.

    This last March was quite challenging, as I was looking to book flights from NYC to Hawaii for April 2015. I ended up booking the outbound as a one way, then I booked the return 10 days later. Booking 2 1-way trips worked well, as I did not want to grab the saver awards while they were available

    School breaks in February can be a difficult time to find award availability in the US, so check out an offseason trip to Europe. We went to the south of France and Spain 2 yrs ago, and it turned out to be a great trip for Winter break

    • Should read “This last March was quite challenging, as I was looking to book flights from NYC to Hawaii for Feb 2015 (11 months in advance).

  21. We’ve done the super-far-in-advance points bookings for this year and last for Spring break. Fortunately, I think schools across the country stagger their week-long breaks a bit — intentionally or not — but their are always a lot of families travelling in late March and early April, especially to warmer weather destinations. So, if you want to travel using points, you need to do it far in advance. We were able to book the Phoenician in AZ this year during Spring training using SPG points. And we already have our Hawaii tickets booked for 2015 (using Avios!).

  22. I was wanting to book Chicago to Honolulu via United Miles for the family over spring break, March of 2015 and there is nothing within a month or so of Spring Break Season. Is this normal for United? Will they open something up later or should we just plan on trying to go the beginning of summer and book that in the next few weeks? Thanks!!

    • @Brandon I was tracking the same route but for whatever reason United blacked out the saver awards for Hawaii for most of March into April. If you want to go during that same time period and don’t mind a West Coast layover, check out Alaska Airlines, which has several flights into ORD. Although you don’t get a lot of points with their credit card signup bonus, they do give you a companion pass which is worth a lot on a RT between Hawaii and Chicago.

  23. This post and comments remind me so much of my travel as a school age kid! My dad worked for the airlines for 37 years (on the ramp), so we flew for free. But, we flew standby and didn’t have a lot of money, so we flew at off peak times to A) Ensure the flights had plenty of available seats, and B) So that hotels and other things would be cheaper. We almost always went on a cruise every October, when they were super cheap thanks to peak hurricane season. As long as I had a “vacation slip” signed and approved by all of my teachers, the absence would be considered excused.

    In the 10th grade, I brought my vacation slip to my English teacher (let’s call her Mrs. Smith) and asked her to sign it and if I could get my assignments the week before I would go on vacation. She looked at me sternly and said, “Summer vacation just ended six weeks ago, why didn’t your family go on vacation during the summer?” Not knowing anything about family vacation planning at the age of 15, I just shrugged and said I didn’t know. So Mrs. Smith told me she wouldn’t sign my vacation slip until I asked my mother why we didn’t take a summer vacation instead.

    So, I went home and told my mom what Mrs. Smith said. My mom looked like her head was going to explode. Through gritted teeth she said, “YOU GO TELL MRS. SMITH THAT NOT ALL PARENTS GET AN ENTIRE SUMMER OFF TO TAKE VACATION TIME. And that your father has to ‘bid’ for his vacation time in accordance with seniority and it is nearly impossible to get vacation time approved in the summer. And that you are a straight A student and have never had any difficulty in the previous six years that we have taken you from school for a week on October.” And there were many other things.

    The next day I went to my English class and repeated to Mrs. Smith what my mom had said. Needless to say, Mrs. Smith was not happy and she refused to sign the vacation slip. It was a big to-do. My mom ended up calling the principal’s office and eventually my absence was excused even though Mrs. Smith wouldn’t sign the slip.

  24. MP: Just a heads-up. The State of Florida just increased the required carseat age to 5. Don’t know if that impacts your planning.

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