How to plan a multifamily vacation

When my daughter, Kaylin, was just 8 months old, we flew to Maui for a week's vacation with my mother-in-law and my husband's siblings and their young children. Quickly I discovered how incredibly awesome it is to travel with other families: Not only did we have built-in adult babysitters when my husband and I wanted some alone time, but my daughter had instant playmates!

Back then, “playing” entailed the older kids entertaining Kaylin with simple beach toys. In the 14 years that have passed, we added more kids to our families,and all six of the Williams cousins (now teens) have had a blast together making their own adventures in and out of the water on family trips to all-inclusive resorts in Mexico and houseboating on Lake Powell.

In other words, the more kids on the trip, the less this mama has to entertain. It's a win-win for everyone.

After a handful of these types of vacations with extended family, as well as a few New England getaways with my college friends and their kids, I've compiled some tips for planning and executing your own multifamily vacation.

Start compromising early on in the process. With multiple families involved, it's likely you're not going to choose a destination that is top-choice for everyone. If there are some deal-breakers on which you insist (i.e., the hotel must have a pool, or you must have your own private bathroom in the condo), make your needs/wants known. But unless you're heck-bent on one specific spot or resort, start going with the flow early in the game, because once you're on vacation with several other adults and children, surely there will be some instances where you'll need to be flexible.

Delegate one main organizer/point-person. For my extended family's most recent trip to the Riviera Maya, my husband booked the resort (after presenting three good options to the other families for a vote), and then booked our flights. While he shared reservation confirmation numbers and the itineraries with all the adults, he was the person who corresponded with the property when any of us had questions. He also dealt with re-booking flights when one of ours got canceled. I served the same role when we rented a multi-bedroom house in New Hampshire for five (!) families; it made sense for one person on our side to communicate with the owner so he didn't have to field questions from all of us.

Viewfinder Tip: Consider an all-inclusive resort or a cruise for a multifamily vacation, as activities for all ages and meals are included in the price.

Let everyone have a say on activity planning. No one likes a bossypants, so even if you are the main vacation researcher and organizer, let other folks (if they want to!) figure out some fun activities or family-friendly restaurants to try. You also can try to delegate some authority: Suggest each family plan one day trip or restaurant meal to spread the work around.

Talk about money up-front. Booking hotel rooms or cruise slots for multiple families is easy: Each family pays for its own room or cabin. But when you're splitting the cost of a rental home, you may need to adjust who pays what if one family is relegated to a sofa bed in the living room and another gets the master suite. Meals, too, can get complicated if a dozen people go out to dinner and people order more expensive items than others. Talk about the finances openly with other travelers before you leave, and a make plan for creating equitable (or adjustable) expenses before you book the trip.

Split up meal prep if you're staying somewhere with a kitchen. Meals always have been one of the best parts of multifamily trips, especially when we've had access to a kitchen. The way we do it, each family is given a designated meal—or two—to prepare, so throughout the course of the vacation, you might “work” a couple times. For all of the other meals, you can simply kick back and be served! (Of course, taking turns with dish washing duties is always nice.)

Share a planning document online. To avoid multiple emails flying back and forth about logistics, keep grocery expenditures, meal plan, flight itineraries, and packing lists on a Google Docs file or other such shared website. This is a great way to keep track of items you plan to share, such as jars of peanut butter and jelly, snack foods, and pool toys. Another benefit: Shared documents just help keep everyone in the loop at all times.

Talk to your kids about toys. Let your children know that the games and toys they're bringing along are for all the kids to share. If there's a beloved stuffed animal or blanket your child can't travel without, a “lovey” about which your child is ultra-protective, the item only should come out at bedtime.

Set down generally accepted behavior rules for kids. Discipline on a multifamily getaway can be tough, since “okay” in your household may be forbidden in another (i.e., video games before bedtime, or using electronic devices in restaurants). While I think it's important not to be a total control freak in these instances, I believe that if you don't want your children playing handheld video games, you need to be prepared to entertain them while other kids on the trip enjoy downtime with screens.

As our children are now teenagers who crave independence, we've had to institute other new rules on our vacations, such as, “Make sure you are always with a buddy” and “After dark, make sure an adult knows exactly where you are.” We also have learned (the hard way!) to spell out consequences if rules aren't obeyed.

Talk about disciplining others' children. Especially if you're watching your friends' children while the kids' parents enjoy time alone, talk to your friends about how they would like you to discipline their kids while they are away are away—lest the situation spirals downward into a toxic situation a la The Slap.

Recognize that you don't all need to be together all the time. Perhaps your family of four wants to head out for a day of sightseeing, just the four of you. Or the active folks would like to tackle a morning hike, while the foodies want to take a cooking class. I say, that's great! On our most recent extended-family trip, we all enjoyed the all-inclusive resort's amenities in different ways: Some of us went to Zumba, others checked out the archery competition, still others planted themselves at the swim-up bar. Outside of these activities, we had a standing plan to meet for dinner in the evening. This helped ensure that everyone had a chance to indulge their personal interests, while still enjoying plenty of “together time.” In my book, that balance is the secret to an ideal multifamily vacation.

How do you ensure a multifamily trip will go smoothly?