6 Steps to Planning the Family Vacation of a Lifetime

Sure, solo getaways can be fun, but nothing beats a family vacation.

According to a 2018 survey by AAA, some 88 million Americans said they planned to take a family vacation within a year. And just about everyone is into the idea of a family bonding trip. As the survey showed, 44 percent of Millennials, 39 percent of Generation X, and 32 percent of Baby Boomers said they planned to participate in a family trip in one form or another.

“Just like generations before them, Millennials see a family vacation as one of the best ways to create memories and reconnect with loved ones,” Bill Sutherland, AAA senior vice president of travel and publishing, said in a statement. “No matter their age, families are going on not just one, but multiple vacations throughout the year to revisit favorite destinations and experience new places.”

While getting away with your crew is something we certainly condone, we must warn you: Family travel takes a lot of effort. And we don’t just mean when it comes to keeping your sanity in check around your relatives.

Planning a trip for multiple generations of family members with diverse likes, dislikes, and needs can be complicated. So, if you’re trying to gather your squad this year for a trip, just follow these five handy tips I learned along the way on my own family vacation — which included my mom, dad, sister, brother-in-law, boyfriend, and 2-year-old nephew — to Jackson Hole, Wyoming this winter.

Multigenerational Family Trip
Stacey Leasca

Choose a destination that’s convenient for everyone.

Picking a destination for your family getaway may be the hardest part of the planning process. Some people will likely want sun, while others want snow, and a few others may want something in between. The easiest solution is to pick somewhere in the middle of all your wants and also all your physical locations.

For me, that meant Jackson Hole. While I live in Los Angeles, other members of my family live along the East Coast, making the center of the country an ideal meeting ground for everyone.

Jackson Hole was not only a geographical compromise, it also suited everyone’s love of the mountains and beyond. The town is full of stellar restaurants like the small dining room inside the ultra-lux Caldera House and more casual bites at Gather. It even has a burgeoning art scene that is on full display at the National Museum of Wildlife Art as well as slopeside on the mountain with an ever-changing installation thanks to the artists at Wildly Creative.

Clearly communicate your options.

To find out where your own family would like to go, try sending out an email survey to every family member attending the trip and see which type of trip everyone gravitates toward from this list: Beach, mountain, desert, city, and national or international. Then, ask about activities and include: Museums, outdoor activities, spa experiences, and dining. From there, you should be able to whittle down options based on people’s budgets, timeframes, and what time of year you’re planning to travel.

Multigenerational Family Trip
Stacey Leasca

Find the right accommodations.

After you all figure out where you’re going, it’s time to think about where you want to stay. While hotel rooms can feel luxurious, your best bet is to stay together in the same space. That way, you can enjoy meals together, plan your days together, snuggle up and watch movies together, and just generally get to bond more.

If you’re still into the idea of getting all those hotel amenities, you could try booking a stay at a hotel residence as we did at the Four Seasons Resort and Residences, Jackson Hole (starting at $2,900 for a two-bedroom residence). The hotel allowed us to still have all the trappings we loved like a spa, a pool, an on-site restaurant, and even a ski valet that helped keep track of all of our equipment on and off the slopes. But, unlike a typical hotel room, the residence came with three bedrooms, a living and dining area, and a full kitchen.This allowed us to all go off and do our own thing for the day, but still have a shared meal at breakfast and dinner. (And a Jackson Hole specific tip: If you’re in it for the skiing, the Four Seasons is one of the few ski-in, ski-out destinations in town.)

The other option for accommodation is to find a home rental. After our stay at the Four Seasons Resort and Residences, we all moved over to the Snake River Sporting Club, (starting at $795/night) located about 35 minutes from the mountain. At the club, we were able to rent a fully equipped four-bedroom home complete with its own kitchen, living room, outdoor fire pit, and hot tub. And there, we were able to feel totally at peace as the home is set on 1,000 acres of diverse western terrain, which happens to also border more than six miles of private access to Snake River and 3.4 million acres of the Bridger-Teton National Forest, making it feel like the most luxurious family camping trip of all time.

The home once again allowed us all to gather together around the dining table for meals, and laugh together. But, more than that, it also allowed us to plan a few unique activities, which brings us to our next point.

Make sure there are enough activities for every member of your family.

Our family trip had quite the spread when it came to interests and ages. The youngest in our gang is just shy of 2 years old while the oldest celebrated his 63rd birthday on the trip. That meant having to plan plenty of varied activities that everyone would be happy with. This is a crucial step to take in planning a well-orchestrated family getaway.

To plan, ask the hotel, residences, or even a homeshare rental owner (such as Airbnb or HomeAway) about what activities are available on the property. If you’re unsatisfied with what can be done on site, ask the manager to list out several activities your group may like to take part in together around the community. Odds are they already have a list of popular vendors they work with.

For us, activities on site at Snake River included some people hitting the mountain for skiing thanks to the free shuttle, while others took part in tubing, cross-country skiing, and dogsledding.

On a warm-weather vacation, you’ll likely have a similar array of options too like snorkeling, surfing, or simply hanging by the beach. No matter where you go just ensure there is access to a number of varied activities that will make everyone happy.

Multigenerational Family Trip
Stacey Leasca

Do one really memorable thing together.

Family vacations are all about a shared experience. That means it’s key to do just one epic thing together so you can all look back for years to come and laugh, cry, or be in awe together.

For my adrenaline-loving family, this meant booking a day trip with High Mountain Heli-Skiing. (Pro tip: We found the operator by taking the advice above and asking Snake River Sporting Club for a list of activities and vendors they liked.)

For one whole thrilling day, the entire family (sans the two-year-old) boarded a helicopter to take six perfect runs down the backcountry of Wyoming. It was the first time any of us took part in heli-skiing, which meant we were all seeing it with fresh eyes. Of course, we were doubly lucky as our guide Charlie was a master on the slopes and our pilot Cooper was an ex-military man more than willing to show us his expertise in the chopper. Needless to say, weeks after the trip ended we still discuss it every day over email and share photos over text.

I can’t express it enough: Splurge on that one perfect day. Be it heli-skiing, renting a sailboat in Cabo, diving with sharks in Hawaii, or spending the afternoon in the art gallery of your family’s dreams in Paris, just go for it. Experiences will always far outweigh anything you could ever buy your family.

Be OK with throwing out all the plans you made.

If your family is anything like my family, things will go haywire on your trip at one point or another. In fact, they’ll likely go haywire fast. For example, on our trip, someone forgot their luggage at the airport (OK, it was me. Are you happy?!), which turned the entire first night into a hunt to find said luggage. And, if babies are along for the ride you better believe dinner reservations will change due to wonky nap times and feeding schedules.

The lesson here is to be OK with the chaos. Just make sure to have everyone’s “must do” events lined up and let everything else happen as it will. Remember: You’re with family. No matter what you do it will be a blessing because you’re all together.

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