Hi Caleb,
Thank you so much for visiting the Disney Parks Moms Panel with your question. I am so glad that you are thinking ahead about planning your dining reservations at Walt Disney World!
I think that overall, early May is a moderate time of year in terms of crowds at Walt Disney World. As there are no major holidays during the time that you mention, I think this will keep crowds moderate.
As to time of day to plan a dinner reservation, if you are looking for a restaurant to be less crowded and with a high likelihood of getting into a particular restaurant, an early or late dinner is probably the way to go. If you look for times before 5:30 p.m. or after 8:00 p.m., you might have the most luck. I find that I am almost always able to find a dinner reservation somewhere at Walt Disney World at 8:30 p.m.!
I suggest that you make reservations as soon as you are able, especially if you are going to head to dining locations that are popular. You can make
Disney dining reservations through the link I provided, or by calling 407-WDW-DINE (407-939-3463). You can make reservations up to 180 days ahead of time, and if you are staying at a Walt Disney World resort hotel, you can make reservations 180 days ahead of your check-in date for up to 10 days of your stay.
I hope that this information is helpful for you, Caleb! Please let us know if you have any further questions.