Strategies for Teachers and others

@Ryan Landrum, we are a two-teacher, one student family, so we understand how tied every aspect of life can be to one school calendar. Living in South Florida, we also understand how far that teacher’s paycheck can go when the cost of living (particularly housing) is so high.

Because we live so close, a trip to WDW is more of a weekend escapade for us than a major vacation, but because of this, we’ve been just about every time of year. The last couple of years, summer has been relatively low crowds. As for the heat, you live in Texas. It would be hot and humid if you stayed home. And going to WDW is always better than staying home.

To me, the real tips for teachers are in how to stretch your Disney dollar. There are ways to get deals on tickets like through Undercover Tourist or Park Savers (if you’re in a union, they like to push Tickets at Work, but in my experience they are usually not the best deal).

We save money by staying and eating off property, but we also have a car. YMMV with that tip, but it’s worth researching and running the numbers for offsite and onsite stays. In addition looking at hotels, look into renting someone's vacation home or time share points.

Look into ways to save money on meals. DDP is rarely a real value, but consider other tips like eating breakfast (cereal, granola bars) in your room, packing snacks or sandwiches so you don’t have to buy as much food in parks, keeping water bottles/soda/Vitamin Water (whatever your beverage preference) in your room so you don’t need to pay their mercenary beverage prices, even keeping a bottle of your nightcap of choice in your room so you aren’t as tempted by the really expensive adult beverages that look so good when everyone is walking around with them. It doesn’t have to be a spartan existence, but exploring options like these let’s you prioritize how you really want to spend your money.
 
I am a teacher in NJ and we get out late June and don't go back until after labor day. So far, the best thing for my family is going in late August. We're doing land and sea in 2018 and the later we went in August, the better the price. Granted, then you have to worry about hurricanes, as well. It's all a toss up, I guess!

I'm a teacher and I have July and August off. I go back the Tuesday after labour day weekend. We've been going to DW the last two weeks of August for the past 8 years. It's awesome! We've always found crowds to be low the week before labour day every single year.

Yep to that, me too!
I also teach and can travel during July/august. We never even look into going during the Easter / Christmas breaks as the airfare is way too expensive.

We usually go in August, but I have to say the end of August is a lot more crowded than when we started going 9 years ago in the summer. They had free dining offers and special offers for the UK the past few years making it more crowded than you might think for the last weeks of August, we have definitely noticed a difference.

Also the heat limits us in terms of how much time we spend in the parks (as DD and DH are heat sensitive). But since that's the only time that works for us , we make it work
 
My wife and I are both teachers with 3 children in a district different than the one we are employed by. We are also DVC owners. We travel early June/late May after the year ends for 10 or 15 days, a week or so during spring break, four or so days for fall break, and winter break for about 10 days. The early summer trip and spring trip(when not Easter) are very smooth and moderate to low crowds. We have the advantage of being relaxed as we know we will be back in a few months. The early summer with a moderate level of planning is always smooth. Feel free to message me if you need any information or have any questions. Happy planning.
 
I am a college professor, so also tied into the school calendars. We actually have a couple weeks at the end of semesters when I can get away, but the kids are old enough now that pulling them out at the end of grading terms gets tricky. We have taken annual trips during early July for the last few years. The crowds were much better than Thanksgiving week, and even better than many of the times of the year which were historically lower crowds. You'll be fine any time in June--it gets busier the later it gets in July. The heat will be miserable. Expect it, prepare for it, train for it, and hope for cloudy days with a light breeze.

Since we are actually paid less than most high school teachers, the most important advice I can give is to earn points from the Southwest credit cards. We have saved thousands of dollars on flights in the last 4 years, probably 40 round trip flights for less than $900 total in credit card annual fees. Even a single card with 50,000 point sign-up bonus (sometimes as high as 60K--but don't sign up for less than 50K!) will get you two roundtrip flights from HOU or DAL to MCO. That's a no brainer for the $69 annual fee. Even better is to get two cards in your name and earn the companion pass. Then DW will fly free with you anywhere you go, and you have 100,000 points which should cover 4-5 free round-trips for BOTH of you!
 
glassslippergirl has it right. I don't see being a teacher as an issue. DW works in a school district. Frankly, we see it as an advantage...they're off all summer, Thanksgiving, Xmas, Spring Break, etc...where I work a typical job with only 3 weeks off. We just go when school isn't in, and thankfully my job lets me work remote, so I can stretch my time off.

Budget is key. We are exclusively offsite people and bring our own food in. I'm willing to bet we spend at least 50% less than onsite people who eat in restaurants. We're here now and are spending 11 days in the parks and 12 total nights in our offsite rental. We're a family of 5. Our total food and lodging costs for this trip will come in somewhere around $1750, maybe a bit less
 
I am a teacher and travel solo. I went in July this year and the heat was brutal, so I went again for a 3 day weekend in December, using one personal day. I have gone over Thanksgiving too. Luckily for me Spirit flies to Orlando from my hometown which makes it very convenient for me. Going in the summer usually isn’t too bad.
 
A different perspective: You are lucky to have designated breaks!

It may not seem that way to you but having the months of June and July as open options is actually very lucky. Many people work in positions where it is difficult to get a week away from work at any time of the year.

I am truly not trying to be snarky, just offering another perspective that might change your approach to the trip. You are lucky to have a set aside time that you definitely can go!

Of your choices, we really like June. I’d go shortly after your school year is over. We have teachers in our family who choose early summer.
 
A different perspective: You are lucky to have designated breaks!

It may not seem that way to you but having the months of June and July as open options is actually very lucky. Many people work in positions where it is difficult to get a week away from work at any time of the year.

I am truly not trying to be snarky, just offering another perspective that might change your approach to the trip. You are lucky to have a set aside time that you definitely can go!

Of your choices, we really like June. I’d go shortly after your school year is over. We have teachers in our family who choose early summer.
I agree with this too! I work for a school system now, but when I didn’t I was lucky to be able to take off a whole week at once. Now I know there are built in times that I’m automatically off & I don’t have to get approval to go.
 
DW is a teacher, but then we live not too far away so we mostly do day trips when we can
 
We're not allowed to take the day before or after any day off, off. Won't be approved.

We aren't allowed to take a personal day attached to a 3 day weekend either. We can take unpaid days though, which I have done in the past. Took a whole week unpaid so I could chaperone my daughter's middle school class at WDW! That was a bit annoying, since it was a school trip. The middle school teachers that went got paid, but since I worked at the high school, it was unpaid time.
 
We are not allowed to use personal/sick time or unpaid days for vacations. We're limited to summer and school breaks. We've been during Feb, April and summer breaks. Weather wise Feb was our favorite, but it was crowded. Late August is the best for us crowd and cost wise, but it's so very hot. Our next trip will likely be Feb 2019, but the cost is about double our August trip. Ugh.
 
A different perspective: You are lucky to have designated breaks!

It may not seem that way to you but having the months of June and July as open options is actually very lucky. Many people work in positions where it is difficult to get a week away from work at any time of the year.

I am truly not trying to be snarky, just offering another perspective that might change your approach to the trip. You are lucky to have a set aside time that you definitely can go!

Of your choices, we really like June. I’d go shortly after your school year is over. We have teachers in our family who choose early summer.

Yes!!! I've always felt teaching was an advantage for this reason alone. You know when you're off and you have a decent chunk of time off. It makes booking, planning, etc.... so easy.
 
I’m a teacher in NY and we always do late August, as it’s really not crowded and quite a bit cheaper than the rest of the summer. Last year I set up my classroom first, then took off for WDW for a week and got back just in time for school to start. By going Wednesday to Wednesday, we got a great deal on airfare too - $225 round trip from Rochester with no layover!

I’ve also never heard of a school district giving you additional days, paid or unpaid, for something that wasn’t a truly exceptional situation, which would not include a WDW trip. Even if it was allowed, I can’t even imagine the work going in to sub planning for an entire week and would much rather just go on a scheduled break instead. Our personal days are only for things that must be done during the school day (legal things, family obligations) and can’t be used to extend a long weekend.

Best of luck!
 
I am a retired teacher/coach in Texas with your exact same situation when I was still working... Football/Baseball. I am guessing you are at a very successful football program because December football is rare at most high schools in Texas.

Regardless, I was fortunate enough to be a long standing employee of my district with flexible administrators. We fly out around New Years' Eve (lots of good air fares as not many fly on a holiday) and stay until the end of week 1 in January. Don't know where you are located but JetBlue flies non-stop AUS-MCO with great rates if you book early, also look at HOU-MCO on Southwest) Usually costs me a couple of personal days but well worth it. If there is a policy of no personal days directly after a holiday, just ask administration to waive. You never know. I once took a NYE trip to Egypt and administration recorded the days as "field trip", I was the head of the Social Studies department!

I would definitely consider Christmas break. Yes, the crowds are crazy but you can still get a lot done if you know the system. We never get in a standby line of over 30 minutes. We are currently at 33,000 ft. and arriving at MCO in about an hour. Still sticking to our similar routine from pre-retirement.
 
Another budget idea for you- my primary credit card is the Disney Visa so I build up a lot of Disney points. We don't do the dining plan for many reasons I won't go into now. So I take the Disney reward dollars and pay for our food while at Disney World. Last July it paid for 6 out of our 8 days of dining and that included table service, quick service, snacks, drinks, etc.

Just a thought for those that are looking to save a little $$$.
 
I’m a teacher/football coach as well. We’ve gone to Disney now 3 times over the past 4 years with another trip on the way in June. We’ve went in June about 5 years ago, did a New Years Trip and cruise one year, a Dec 18th - 22nd trip one year, and a spring break trip. I’m in Illinois and July/Aug is summer lifting and mini camps, so basically late June through November is out for us because of football.

The best scenario for us is when Easter is late because our district then does an early spring break in March (this happened last year). This helps us go when prices aren’t so high (we did a parks/cruise combo last year). Problem is we live in a different district with a different schedule and my kids schedules don’t always match up. Last year we pulled the kids out a week - it was the last time as my son in now in 7th grade and misses too much.

We wrap up school the 3rd week of May and I would love to head down right after, but my daughter does dance and her recital is always the first week of June.

We get two personal days a year that we can use whenever, so wrapping them around a three day weekend isn’t out of the question.

So, early June is our standby, if the schedule doesn’t allow anything else.
 
Not a school employee. I agree with others about vacation time for school employees, even if one is a coach, being easier to plan around.

I had a week of use it or lose it time at the end of November. I gave my boss a letter on Nov 30 outlining my days off for December. I am the only full time employee, others are contract workers who do their specific job and that's it.

I stated that I would only be in the office Dec. 27th for that week. Dec. 27th he said 'I've got one more thing for you to do, but we'll get to that tomorrow. 'Uh no, we won't. I'll be out of town using my remaining vacation days. We talked about this and I gave you my time off in November. '

For longer trips, I have to find a volunteer and train them on a few limited tasks and work like crazy before and after vacation to get most of the work done. Very difficult to leave for several weeks on end.
 
I am also a teacher and coach (football and track). Our track season ends when school ends in late may an even though summer football workouts start immediately once school ends we still take the time for family vacation. We normally vacation the second week in June and have Always found it extremely enjoyable during this time period. Yea the crowds are high but they are no matter what time of year. We also tried to go for the first time the first week of August one year. Although it was extremely hot, it was still a fantastic time with manageable crowd. For us there is nothing better than early June. It feels like a great kick off to summer!
 
Most people have far less flexibility because they only have 2-3 weeks of vacation per year. I think if you avoid 4th of July week, any of those summer weeks will work. Given your schedule, I'd consider trying to schedule a longer trip so you can take a more relaxed pace. Lots of people don't have that as an option.
 
I didn’t read through all the replies but I’m a teacher as well. We get out the week before Memorial Day. We go to Disney the first full week of June so I can have Memorial Day week to pack and prepare. It’s not really bad crowd wise. The heat was worse in 2016 than this year but it rained more this year. We do rope drop-midday Break-then evening touring (usually til close). I do lots and lots of planning and research to make the days go as smoothly as possible.
 

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