Hi Angela,
Welcome to the Disney Parks Moms Panel! I am delighted to discuss this
dining plan question!
On the day you checkout from the first resort hotel, you can redeem your remaining dining plan entitlements up until midnight. I always create a chart of our dining plans to be sure I have calculated dining plan entitlements correctly and that I know exactly how many entitlements we will use for each dining experience. Doing the chart helps me to make sure that we use all of our entitlements and I like to make sure we have at least one entitlement remaining for the day we checkout. It actually may be possible for you not to need to use any dining plan entitlements from the second dining plan on the day you check-in to the second resort - it depends on the number of meal entitlements you have remaining from the first dining plan!
We did a split stay on the Disney Deluxe Dining Plan last summer. When we checked out of the first resort hotel, we still had two dining plan meal entitlements remaining, so we used those on the day we checked into the second resort hotel. It was lovely. I do have a few additional tips - remember that your dining plan entitlements are calculated per night of stay so if you are staying for six nights on the Disney Deluxe Dining Plan, you would have 18 meal entitlements per person 3-years old and over. Also, know that entitlements are all loaded onto your account when you check-in and you can use them in whichever order you choose. To check the number of entitlements a restaurant requires, go to that restaurant's home page and, if available, click on "Some Dining Plans Accepted." A pop-up menu should appear that illustrates the number and type of meal entitlements required.
Angela, my family always finds a dining plan to be a great value. I trust that you will as well!
Magic, memories and Minnie Mouse hugs,
Donyell