The first things I do is print off a copy of my vacation spreadsheet. This is my go to tool for all of our vacation planning. I use a one page "at a glance" structure for my planning, that you can see in the below image. This spreadsheet lists every checkpoint in our vacation, where we need to be, with times and reservation numbers. For our upcoming trip we won't have housekeeping, so my anticipated tips will be for Magical Express, Bell Staff and Table Service meals. I take a marker and notate how much money I will need to tip for each situation. Then I list it out how many of each type of envelope I will need.
Over the past several vacations I've noticed that I use some pretty standard tip amounts when traveling with 2 people. $5 goes into the envelopes for the magical express and bell staff, $10 for breakfasts, $20 for table service lunches and $40 for signature dining experiences. These amounts may seem high for you as we often order wine or cocktails with a meal. You should figure out what amount will work best for your family.
Next I print our labels for the front of the envelopes with a couple of graphics and little note of thanks for the service. This year I used the new DVC Mom logo for our envelope image. Included in the design I usually add something that says "Tip Inside," because I have on occasion run into the odd cast member that just thought I was giving them a note.
Finally I place the labels onto the envelopes and stuff them with the appropriate amount of money and seal them lightly. Handwritten on the back of the envelope I add a note stating where the tip should be used such as "Bell", "Boma", or "Magical Express. This way when I grab an envelope I'm sure that the appropriate amount is inside.
I then group my envelopes by the day that they'll be used. If you use the Passporter Guides, you can slip the tip envelopes into your pass pockets. These days I use a document holder when traveling so I group all of my envelopes by the day that I will be using them and clip them together with a paperclip. Then I stick them in my document case and I'm ready to go!
For more tipping tips, follow this link to my check out my original tip envelop post here!