Hi Lisa.
In order to take advantage of the Free Dining Plan promotion, your best bet would most definitely be to book 2 separate reservations. Book one as a resort-only booking for 1 night and another for the duration of your stay so that you can take advantage of the great offer. On that first day, enjoy your Resort Pool, shop at Downtown Disney or even play a round of mini-golf at one of the two great courses on the property! If you prefer to have a Cast Member make your two reservations for you, call in at (407) 939-7675.
Upon making your two reservations, simply have them 'linked' in the system. When you arrive to check in, advise the Cast Member that you have a continuing reservation beginning the next day, so that they can do their very best to ensure that your resort experience can hopefully be seamless. When you check out and 'into' your longer stay that includes your park tickets and free dining plan the next morning, mention again that you'd prefer not to have to change resort room locations and everything possible will be done to lessen that likelihood. On the morning of Day 2 you're set to head into the parks and begin using your Free Dining!
You can already make Dining Reservations as you wish by visiting
Online Reservations. These can easily be linked to your Resort Stay later so that you'll be able to see everything in conjunction when you sign in. If you need assistance in doing so, feel free to visit me again or simply call and speak to a Cast Member at (407) WDW-DINE and they can help you link your dining to your resort reservations once you've made them. For reservations that require pre-payment such as dinner shows, you'll want to have your Reservation with Dining Plan already in place.
Thanks for visiting the Moms Panel Lisa! I hope you'll visit me again soon!
Wishing you a simply Magical time at Walt Disney World!
Kirsten