We Survived Four Generations in One Vacation Home—These Tricks Made All the Difference

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A multigenerational family trip in Key West that actually worked, thanks to smart planning (and the right rental).
My family is anything but perfect. In fact, I'd go as far as to say that we're a group of disconnected connected individuals. Everyone has their own way of living, and some of us even speak different languages. That's probably true of most multigenerational families, especially those with members born in different parts of the world.
I'm first-generation American, which means my parents, grandparents, and some extended family members all came from different parts of the world. Naturally, we all have different ideas of what's "normal."
Still, we just got back from a family reunion, and despite our numerous differences, we all had a wonderful time. And yes, being together is the greatest joy of all, blah blah, but, truly, the planning made a huge difference.
Without sounding too braggadocios, I nailed planning for our family reunion with multiple personalities, generations, and needs. And if you're planning something similar for your large and questionably amendable family, here's how you can survive it, too.
Planning for a Multigenerational Family Reunion
Planning can be the most dreaded part of a big trip, especially when everyone has different wants and needs. My family ranges widely in age, so we needed to make sure everyone felt comfortable in where they were staying, what was available to them, and what we were eating.
Here's the step-by-step process we took to plan a stress-free trip.
Pick a location that works for everyone
Choosing the right spot for your reunion is crucial. You want a location that offers activities for the whole family and isn't too far from where everyone is traveling.
For our family, that meant booking an Airbnb in Key West, Florida, called Lunara Bay Homes. The special part about this Airbnb is that the same company owns all the homes in a private, gated community, so it feels both safe and connected. And if your family is on the larger side—or just needs some separation—each household can rent out its own home while still being only a few minutes apart.
It also doesn't hurt that the homes are stunning. Each property features modern kitchen fixtures, a private pool, a fire pit, and plenty of space to gather.
Get everyone settled early
Once you've picked out the right spot, the next step is figuring out what each person needs to feel comfortable. For our family reunion, we made sure to pre-assign rooms to save arguments.
This was super easy with Lunara Bay's listings, which show photos of each room and clearly state how many guests the home sleeps and how many bathrooms it has. And here's what might have been the highlight of the whole trip—everyone had their own bathroom. Coming back from the pool or beach and heading straight to your own shower, without fighting over who goes first, was a game-changer.
Once everyone found their corner of the house, the fun began. We played music on the outdoor TV, the teens jumped into the pool for a game, and my abuela found a shady spot to watch it all unfold.
Plan meals and snacks
Feeding a large, diverse group isn't easy. In my family, there are allergies, dietary restrictions, and personal preferences to navigate—my uncle is pescatarian, my cousin is allergic to gluten, and others just have strong opinions. So it was important that we planned our meals accordingly.
In the past, we'd make a shared grocery list and send one unlucky person to the local supermarket after arriving to haul all our groceries back to the home. This time, Lunara Bay's guest experience managers contacted me a few days before our stay to take our grocery order. They stocked everything and put it away in the kitchen before we even checked in.
This meant we can get straight to cooking. A few hours after arrival, we were grilling hot dogs outside; the next morning, everyone made their own yogurt bowls for breakfast.
Don't skip the local specialities
While planning meals saves time and money, it's also fun to try regional favorites. In Key West that meant Key lime pie. During one of our pool days, a few of us ventured to Moondog Cafe to grab a whole pie to bring back. It was gone in 15 minutes.
Choose activities everyone can enjoy
When you bring multiple generations together, everyone has their own idea of what a "fun day" looks like. To avoid chaos, plan activities ahead of time and make sure plans work for both older and younger family members.
For our group, that meant a kid-friendly sandbar excursion hosted by Brightwild Adventures. They arranged a private shuttle for all 12 of us to pick us up right at our home, then took us out on a boat stocked with unlimited snacks, lunch, wine, and beer.
The boat brought us to a sandbar where the water was clear and reached about 4-5 feet deep. Still, the folks at Brightwild provided life vests for all the kids (and a few cautious adults) and made sure they fit properly before sending us along. Kayaks and paddle boats were available, and we spent hours soaking in the sun and laughing at our failed attempts to climb the sandbar's rope swing.
It was a memorable day for everyone, especially my abuela who was on a boat for the first time. Seeing her reaction to the turquoise water was priceless.
Tips for a Drama-Free Family Reunion
After getting back home to New York, I realized that I might have pulled off the impossible: several days together without drama. No fights between teens on who gets what, no argument about what to do, no meltdowns over meals. I'm not sure if I've cracked the code just yet, but I'd thought I'd share some tips I discovered along the way.
Assign a point person. Choose someone the whole group trusts to represents everyone's individual needs. This will help avoid group decision fatigue. Just make sure to check in with your point person, too—maybe buy them a drink one night.
Stock the snacks. If you can arrange for them to be stocked before arrival, even better. If not, bring something everyone likes before the hangry vibes strike.
Respect everyone's downtime. Make sure there's enough space for everyone to decompress, or agree on quiet hours. If your group includes small children, consider implementing quiet hours earlier in the day so it doesn't get in the way of their fun.
Book at least one thing in advance for the whole group. Choose one activity that everyone will enjoy, book it (including transportation) ahead of time, and make sure everyone knows what to bring, including a tip for any guides/instructors. Not only is it a great way to explore the area you're visiting, but it also offers more opportunity to bond and problem-solve together.
Leave space for spontaneity. Some of the best moments are unplanned, like when we all decided to stop by Publix after the beach to get everything we needed to make s'more's in the fire pit. One of my favorite memories is watching my abuela's face as my cousin's marshmallow caught fire.
What We Took Home from Key West
Looking back, I realized this trip wasn't just about getting everyone in the same place, we also had to make it work once we were there. And somehow, it did. We laughed more than we argued, solved problems together, and even managed to all lose money to abuela during mandatory Bingo night.
Ultimately, our time in Key West was proof that our chaotic, opinionated, multilingual crew could not only coexist but actually enjoy each other's company. Maybe it was the sunshine. Maybe it was the private pool. Maybe it was the fridge stocked before we even walked through the door. Whatever it was, we left with full hearts, lighter suitcases, and a few new inside jokes. And that's the kind of souvenir I'll take over a magnet any day.
Read the original article on Parents
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