Hi Brenna!
I'm thrilled for you to be taking a subsequent trip with your son to Walt Disney World Resort! I have personally traveled in both May and August. You can expect both weather and crowds at an elevated level during August, but with careful planning I can assure you Pixie Dust flies 365 days a yEAR!
I'm uncertain of your son's age, but be prepared for rain showers in the afternoons. If he's of the napping age, utilize this time to recharge back at your Resort hotel and enjoy a book or quiet time. If he's older, watch the masses scatter from the Parks and enjoy your favorite attractions with little to no wait!
The silver lining with higher crowd levels will be the extended Park hours. Although August park times are not quite released, check back
here to begin planning your itinerary. I highly recommend staying onsite at a Disney Resort hotel to take advantage of Extra Magic Hours and complimentary Walt Disney World Resort transportation.
My other suggestion to you, Brenna, would be to check out the website touringplans.com. The site offers outstanding advice during higher crowd level weeks to guide you in parks to attend or avoid, based on historical attendance.
This may sound simple, but our family loved our August Walt Disney World vacation for the ability to swim at 10:00 in the evening! One of my best memories includes a late night swim after viewing the fireworks at Disney's Polynesian Resort beach area.
I wish you a MAGICAL vacation, Brenna!
Visit us again soon!
Sherri