When we travel together for a week every 1-2 years, our 4 families
don't sightsee or visit the parks all day, every day, as a large group.

With 3 generations, 8 adults, and 9 children under age 5

on our next group vaca, we all need to occasionally relax in our own spaces.

Spacious lodging is more affordable offsite, for sure. We have the BEST time when we alternate spending a few hours together in smaller groups with splitting up according to whatever everyone wants/needs to do next. It's low pressure and everyone is pretty flexible so we have a BLAST together!
- KEY: We all keep in touch via a family text thread with where we're headed and any changes in plans.

So far, we've always all stayed at the same resort property for convenience, especially with swapping around child care (ex., taking some kids to a playground or splash area while other littles/parents/grands are napping). We've done this at WDW resorts, area offsite timeshare resorts, other destinations like Williamsburg, Myrtle Beach, etc. It's always worked very well for us.
Each family has:
- been self-reliant with transportation (car, Uber/Lyft, shuttles, etc.), occasionally using fewer cars so a couple may stay out later, have dinner & drinks, Uber back
- shared their priorities in advance re: the main thing(s) they hope to see/do during the trip, limiting those to just a couple satisfiers
- clarified expectations re: the amount of time we'll spend together vs. as individual families, especially if one couple/family has recently been through a stressful period
- been tolerant of differences in activity/sleep needs and speed of getting ready to go (separate transportation helps with this)
- either purchased take-out or prepared one meal for the whole group to share or taken everyone out together for a meal of the host's choice - so we have 4 group meals (either lunch or dinner) over the course of the week - sometimes a birthday celebration BBQ or pizza party (kept fairly simple) - and all the rest of the meals are up to each family to handle conveniently for themselves
Consider for your group...
- How flexible is everyone in your group?
- Can they appreciate the benefits of the offsite experience (usually more in-room amenities and more room to gather and relax in each other's suite, condo, or pool home) or will they be looking at the offsite location/transportation as an overarching negative that impacts their vaca?
- Do they like the independence of driving/parking or hate it when on vacation?
- How comfortable are they with ride share services?
- What are their touring/sightseeing styles? Rope drop, sleep in, partial day, all day/evening, commando, laid back? Are they similar to one another or not?
- How would more limited transportation options affect their enjoyment of the parks, given their touring styles?
- Would you have to shorten the trip due to finances if you stay onsite? (We don't really cut loose from work pressures and hit "relaxed vacation mode" for several days so having a full week is more important to us than having first choice of lodging - YMMV.)
Would love to read about other people's experiences with multi-generational travel. What made it work well? What didn't?