Should we do every park in one trip?

No. Pick two parks for a 5-day trip. Trying to hop between all four will exhaust the grandparents and cause meltdowns for the grandkids.

How do we handle dining reservations?

Book your sit-down meals for lunch rather than dinner. It provides a cool, seated environment during the hottest part of the day, and it's easier to get tables for large parties.

Planning a Multi-Generational Disney World Trip

Prioritize a pace that accommodates both toddlers and seniors by scheduling mid-day breaks back at your resort. Book your dining reservations exactly 60 days out and utilize Disney Genie+ or Lightning Lane passes to minimize time spent standing in long, exhausting lines.

Establish a base-camp. Choose a resort on the Disney Skyliner route or the Monorail loop. This allows grandparents to head back to the room for an afternoon nap without needing to fold up strollers or wait for crowded buses.
Coordinate your touring speed. Accept that you will not see everything. Plan for 'morning-only' park days where you arrive at rope drop, leave by 1:00 PM for a swim or nap, and return for dinner only if the group has the energy.
Leverage Disability Access Services. If a grandparent has mobility or stamina issues that make standing in queues dangerous or impossible, look into Disney’s Disability Access Service (DAS) requirements well before you arrive.
Rent mobility scooters. Even if grandparents walk fine at home, the 'Disney mile' is real. Rent a scooter from a third-party vendor (like ScooterBug) to have it delivered to your hotel; it saves legs and keeps the whole group moving at a consistent pace.

Should we do every park in one trip?: No. Pick two parks for a 5-day trip. Trying to hop between all four will exhaust the grandparents and cause meltdowns for the grandkids.
How do we handle dining reservations?: Book your sit-down meals for lunch rather than dinner. It provides a cool, seated environment during the hottest part of the day, and it's easier to get tables for large parties.