The Crucial Things to Consider When Planning a Multi-Generational Holiday Trip

Find a destination that’s easy (and cheap) to fly to.

The mantra of planning these kinds of trips is “the simpler the better,” and that starts with your locale. And tempting as it might be to have the whole mishpacha fly to the little slice of paradise you found in the far-east Caribbean during your last solo cruise, getting there can be a logistical nightmare. Never mind flights to hard-to-reach destinations cost a fortune, complicated itineraries also open up the door for missed connections and long delays. And for those traveling with small children, hustling through multiple airports is a mission.

Opt instead for a destination with a large number of nonstop flights from the cities where your family lives. This can include a ton of Mexican destinations, as well as much of Florida and even Hawaii.

Look at somewhere within driving distance.

Though you may only have one or two people traveling in your party, chances are some part of your family will be shelling out for four or five plane tickets. So you may want to look at a destination that’s reachable by car rather than an island or far-flung foreign country. Even if that drive is 12-14 hours, it’ll still be preferable to paying for five flights anywhere, and the less stressed people are about money, the happier they will be.

Consider your family’s planning styles.

It is important to remember that the way your family plans trips may not be the way, say, your in-laws plan trips. Perhaps your family is happy to have one person take control, plan an itinerary, and send everyone a bill. But you may have newer family members who consider vacation planning a more collective experience. If that’s the case, you need to make sure they feel like they had some input in the process, or you won’t get much buy-in and likely less participation. Though you might consider it a logistical hurdle, making sure everyone’s planning styles are respected is an important early step.

Be realistic about everyone’s budget and comfort level.

You, the intrepid world traveler, may have no problems spending a week in a hostel dorm room. Your septuagenarian aunt and uncle who have elite status with SPG, however, may need something a little nicer. That said, your cousin with two kids under four who just bought a new house might not have the budget for a luxury resort. Finding an acceptable resort is a balancing act that can sometimes prove impossible and a big reason why some families just opt for the 10-bedroom villa.

Before booking anything, ask everyone what their legitimate budget for lodging might be. Then use that as your standard when searching resorts. You may find something that’s a little out of some people’s budget, and it’s still fine to run it by them. But you will also need to offer more-budget options that would still be acceptable to your family members who are regulars at the St. Regis.

Think long and hard before getting that giant house.

Ten-bedroom villas on the Mexican Riviera might look tempting, what with their infinity pools and thousand-square-foot patios. But if your family can’t afford a staff to cook your meals and clean up after you, the diffusion of responsibility can lead to a vacation of chaos.

Imagine you have 15-20 people in the same house. Making food for that many people is no small undertaking, and it will typically fall on the shoulders of whoever is nice enough to cook the first time — who after about day two will start getting reeeeal resentful. Or it won’t happen at all, as everyone just kind of sits around and waits for someone to start cooking. Same goes for cleaning, both in the kitchen and everywhere else in the house.

Sleep and activity schedules can get complicated in a big house too. You may have younger people in the house who don’t necessarily feel like going to bed after 7:00 PM tubby time for the little ones. And you may have an older relative who lives by the credo, “Nothing good ever happens after 8:00 PM.” Those people will all be on vastly different sleep schedules, and if the young people come home at 3:00 AM and wake everyone up, it’s a recipe for drama.

Point is, that house might look nice, but in practice, it’s a logistical nightmare. Opt for individual rooms, condos, or separate Airbnbs so that everyone can enjoy family time during the day and then go back to their much-needed private quarters in the evening.

Lean toward condos versus hotels.

Resorts are likely a better alternative than a big house or hotels, both because they offer separate condos where people can operate on their own schedules and because they offer activities, meals, and other entertainment you won’t have to plan. Condos also often come with kitchens, if you do feel like having dinner at home a couple of times. And multi-bedroom setups allow for the best cost efficiency. I might not want to share a hotel room with my brother and his wife, for example. But splitting a two-bedroom condo — which is usually about the same price — just feels like being roommates.

Get all the info on childcare.

The childless among us really have no idea all the little costs that go into having kids. Childcare on vacation is a big one, and every hotel and resort has different options. Some include childcare in the price of your stay, and offer kids clubs where you can drop your kids while you go off remembering what life was like before them. Some charge for said kids clubs, which needs to be factored into the cost of the resort. Some offer none at all, which means family members with small children will be limited in what they can do.

Think about what different people want to do and research activities.

Nothing buzzkills a family vacation faster than starting each day with a rousing game of, “I dunno, what do you wanna do?”

So finding a resort with activities that fit as many people’s interests as possible is crucial. You may be a big diver. Your cousins may prefer doing food tours. Your father-in-law may just want a big pool. Regardless of what your family enjoys, think about everyone’s interest — or at least what you know of them — and find a place that has as many as possible.

That said, planning large group activities, like fishing charters or golf excursions, can be a challenge since budgets and interests vary. Even if you’re leading the trip planning, leave group-activity planning to the people who want to do it as they’ll have the most drive and motivation to make it happen. Don’t force anyone into doing activities they aren’t interested in doing.

Plan meals both separately and together.

Again, cooking food for 15-20 people is an unenviable task. As is trying to figure out a bill for 15-20 with multiple families and multiple budgets. Yes, the idea is to have some togetherness over the holidays, so you should still plan a few big group meals despite whatever headaches it might bring. But you also must absolutely plan most of them separately, keeping with the mantra “the simpler, the better.”

Spell out the logistics for everyone.

This means about two-to-three weeks out, send an email to everyone detailing all the pertinent info they’ll need once arriving at the destination. A good guideline for explaining those details is to imagine you are writing it for the youngest literate member of your family. Tailoring the whole thing to an eight-year-old will, hopefully, ensure nobody gets confused.

This email should include everything from the address and phone number of the resort (older people may not be so big on Google) to airport transfer options and how meals will work. Are you getting communal groceries? Cool, spell out the time and place you’ll be going and how much people should budget. Detail how to find childcare and where activities are. Offer contact info for group activities people might want to plan. The less ambiguity the less confusion, and the simpler language you use, the more people will understand.

Remember to have fun! But not too much fun.

The point of this whole thing is to give everyone a few days away where they can cut loose around people who literally have no choice but to deal with it. So make the most of it! It’s not everyday you get to knock back shots with grandparents or share beers with cousins from across the country, so once you’re there make every attempt you can to have a good time. That said, overconsumption has been known, in SOME cases, to lead to unplanned family drama. So just make sure to drink responsibly, even if you have nowhere else to go.