With an extended family getaway, it means getting people together who don’t usually share the same space. Read on for expert tips from Kid & Coe’s hosts on how to make the best of a multi-generational break—plus our best tip for solving family politics!

Before we dive deep, Zoie Kingsbery Coe, founder of Kid & Coe, shares her five essential multi-family travel rules:

  1. Always book a daily housekeeper from 9 a.m. to 12 p.m. It sounds like a lot, but when you divide it up, it’s the cost of a dinner out.
  2. Buy groceries freely and split the cost at the end of the trip.
  3. Book babysitters for a couple of nights a week to help with dinners and bedtimes.
  4. Everyone has to have their own car.
  5. The person who takes the lead in booking gets the biggest room.

Now, let’s dive in to everything you need to know about planning and booking your extended, multi-family vacation together!

Where to start

“How many times do you actually get some time out and gather all your favorite people together at one place at one time?” asks Susanne Frenk of Windrift Hall in Coxsackie, New York, a country manor house with spacious grounds and room to sleep up to 13. She counsels towards the “seize the moment” philosophy:

“Switch up the routines and get yourself a personal chef, a personal fitness trainer or yoga instructor, find a local forager showing and explaining nature around you and pick up some dinner items on your way. Work with the locals, get your meat from a local farm, pick your own flowers or apples at a local orchard. Bond over new experiences and expand your horizons together: you’ll be surprised how family dynamics can be switched up when you switch your routines.”

Get practical

When you bring families together, personal space is often at a premium—and it can be a problem. Look for properties to rent with an extra building, apartment or guest house for those who don’t want to be woken by children at 6 a.m. and make sure there are multiple lounge spaces so the whole group can spread out and split into smaller groups when needed. There are other essentials: a dishwasher and outdoor space.

“The best thing to look for is a home with space to spread out and many nearby activities so that no one feels trapped,” says Lauren Aichinger of Clearwater Cabin, a Catskills lodge sleeping up to 14, plus babies. “Kids should be able to do kid stuff without bothering the adults and adults should be able to relax without feeling guilty.”

Appoint a chief

Clio Wood, owner of the 8-bedroom Manoir la Croix Residence in France, says that every big group needs a chief. “Someone has to be in charge—someone who is not afraid to tell people what to do! Give this person money from each family unit to put into a pot for the week and use this to buy group groceries and pay for meals when out. And make sure you buy this person a really nice bottle of wine to say thank you.”

“Keeping the communications simple via your chief really helps the property owner/manager as well as the holidaying group. If email gets a bit confusing, try a Doodle poll for decision making or the old-fashioned phone for more involved discussion.”

Avoid bedroom bust-ups

Think about sleeping arrangements at this planning stage too. “A recent group left after four days because they couldn’t get the kids to sleep when they were sharing a room together,” says Lauren. “The parents were exhausted, kids were cranky and they just gave up. Sleeping arrangements are important to consider!”

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“Most people can’t decide which bedrooms to assign to which families and whether or not all the kids are allowed to share one or two rooms or if they have to be with parents,” says Clio. “I suggest having a discussion about this early on so you don’t end up with fisticuffs when you arrive. But also be flexible about your setup. You don’t want to miss out on a really amazing property and fantastic holiday just because you can’t decide who’s bunking with whom.”

Think about entertainment

When you’re choosing a property, take into account what there is to do nearby so there are some options for all the family to enjoy. Colleen advocates for planning new things together and sharing the organization so nobody feels overburdened. Taking part in the planning gives each group a sense of ownership too—they’re not just along for the ride.

“We all have a job each day. Each couple takes turns being an activity planner, grocery shopper and babysitter. We each got to make the vacation feel like our own for a day.

“I’m a true believer that a shared experience can bring people together. This past vacation we rented a bike with a huge front bucket for the kids. It was fun to learn how to push two 4-year-olds and an infant in a car seat around town and then watch my family do the same. The kids loved it as well and it’s become the number one memory from the trip. In the past we’ve put together small cooking competitions, visited obscure tourist spots and rented kayaks. These shared moments give everyone something to focus their attention on away from how tricky it can be to travel with extended family.”

A little bit of research before a trip—checking out local attractions via the tourist board website for example—can help make this happen. Asking the property owner what they can recommend is also a great tip for planning offbeat family entertainment.

Navigating family politics

There’s just one thing to do when the going gets tough:

“Family politics? Drink wine and have a time out,” says Clio.

“When things go wrong—in my book, have a nice glass of wine and breathe for a few moments. What else can you do?!” says Lauren.

“Bring wine. Lots and lots of wine,” says Colleen.

Looking for a place to book your big group? Check out our list of properties for more than 10 guests at Kid & Coe.