How to Plan a Family Vacation That’s Fun For All (We Promise!)


By Dawn Van Osdell

Even as you’re gearing up for Spring Break, you’re probably already planning for the summer months ahead—figuring out where to take the family for a week or two of vacation. Or possibly, trying to decide if you even want to bother when you’ve got little ones who require naps, have short attention spans, and are often prone to meltdowns. While it can feel daunting to pull off a family vacation that’s enjoyable for adults and kids alike, it can be done—and has been done, by many a courageous parent before you. 

The effort to travel with your kids is well worth it for the shared memories and experiences you’ll build, says Cathy Decker, president of Decker Royal Agency in New York City. She’s traveled with her three kids since they were very young: to toil at a dude ranch in Wyoming; to snorkel in the Caribbean; to hike through the Wild West. “Travel makes kids more curious, it makes them more interesting, and it often makes them appreciate what they have, when they learn about the ways others live,” she says. It also fosters tolerance and makes kids—and the moms and dads who take them out of their element—brave.

Here, we’ve rounded up vacation ideas and tips for families with young children. Now you have absolutely no excuse for staying home!

Travel makes kids more curious, it makes them more interesting, and it often makes them appreciate what they have, when they learn about the ways others live.
— Cathy Decker

First Things First: Where-Oh-Where to Go?

Do you have a baby who needs to nap? A preschooler who’s ready to explore (and is hard to contain)? An adventurous tween who’s ready for a new challenge? Consider your family’s skills and abilities, as well as your passions. “Involve everyone in the planning part of the process,” advises Dan Austin, founder and president of Austin Adventures, an adventure travel company in Billings, MT, that often creates customized trips for families. “Ask them what they want to do and where, and look for synergies.”

Be sure to consider the amount of time you have, as tacking a few days on to the tail end of a family wedding is different than a full week away from home. Also, factor in the purpose of your trip: Are you celebrating a life event? Looking to learn about a different culture, or practice a new sport? Or do you simply want to relax together? “We’re different travelers at different times in our lives, and we travel for different reasons,” says Decker, who gifted each of her kids trip to Disney World for their fifth birthdays; by the time they were teens, she was taking them on European vacations, and hiking in Whistler, BC.

Consider the All-Inclusive Beach Resort

Even if an all-inclusive resort is not something your pre-kid self would ever have contemplated, it’s often the easiest way to travel with kids, says travel writer Linda Marsicano. Many resorts offer opportunities to be both together and apart—thanks to family-geared events and also kids clubs, which give parents a break from family responsibilities. “You just don’t have to think much” at these places, says Marsicano, who recently vacationed at an all-inclusive in Jamaica with her six-year-old twins. “There’s no worry over where to go for dinner or what to feed a picky eater. If your kid wants a smoothie, she can try it and if she doesn’t like it, you don’t have to be annoyed that you’ve spent nine dollars on it, like you would if food wasn’t included in the overall price.”  

All-inclusive resorts are often the easiest way to travel with kids

All-inclusive resorts are often the easiest way to travel with kids

Decker concurs. “My kids grew up at Beaches resorts in Jamaica and Turks and Caicos,” she says. “At Beaches in Negril, every day our butler packed us a cooler of fresh fruit and drinks and a Scrabble game to play at the beach.” Both parents and kids would take off for the day with walkie-talkies, so they could stay in touch about what they were up to.

Resorts are appealing even as kids get older, giving them opportunities to learn to scuba dive or paddle board, go on boating trips, even volunteer in local communities—such as the voluntourism program offered by the Sandals Foundation in the Caribbean. Make sure you do your research when choosing a resort, as not all activities, excursions, and food and drink are included. You’ll also want to look at what the surrounding area has to offer, if you’re interested in exploring beyond the resort grounds.

Are You Ready for (Outdoor) Adventure?

Even families with young children can tackle outdoor adventures if they tailor them to kids’ abilities. “Sometimes we underestimate our kids, doubting their ability or stamina, or worrying more about their comfort than about what they’ll get out of a trip,” says Marsicano. She admits to squelching her husband’s love for traveling to national parks because she feared their girls, toddlers at the time, where too young to hike. When she finally gave in to his fervor, she was surprised and impressed not just with her kids’ hiking ability, but also with their enthusiasm. “By exposing them to new challenges at an early age, we helped to spark their love of the outdoors and their love for a challenge,” she says. Her girls were so proud of their new skill, later that year they were easily convinced to try skiing.

If time or budget constraints necessitate your staying close to home, consider camping. Car camping—essentially, driving to a campsite and setting up a tent—is a good prelude to diving into more remote roughing it that requires you to purchase expensive gear and equipment. If you have the time and means, though, adventure companies can provide guided hiking, biking, rafting, or horseback riding excursion with experienced guides; choice accommodations; and a little handholding. Regardless of the type of outdoor trip you plan, Austin says most families tend to pack (and get stuck carrying) more than they need. He’s a fan of keeping it simple with a few garments made of moisture-wicking fabrics that can be washed in a sink and will dry overnight. And he says he “can’t stress enough” the importance of bringing comfortable shoes.

Exploring the Urban Jungle

If your family’s interests align more with museums and zoos than close encounters in the wild, visiting a new city may be the right adventure for you. Consider whether you are willing to fly or would prefer to visit a city within driving distance, then choose a place that offers something for everyone—perhaps a mix of ballgames, theater productions, shopping, and trendy dining options. Frequent city traveler Julia Rogers, a San Francisco resident and mom to 7-year-old Bella, advises families visiting a new city to do plenty of research to get kids excited about an upcoming trip. She suggests reading a city guide book together and marking spots you’d both like to see; and zooming in on places to visit using Google Maps, so you can virtually explore before leaving home.

It’s important to remember, especially with city trips, which can be overwhelming, that kids have limited stamina and attention. When Rogers and her husband visited Rome and Florence with Bella last fall, they chose a few things to explore each day, then let the rest of the day unfold naturally, so they didn’t feel overly rushed or stressed. “We’ve learned it’s best to do some homework, but never to over-plan the day,” she says. “Otherwise, you’re doing an exhausting march where no one has any fun.” She also recommends purchasing a pass for museums and other attractions that can be used over the course of a few days, so you don’t waste precious time waiting in lines for tickets.

give your tween a camera to let her capture her favorite travel moments. they may surprise you.

give your tween a camera to let her capture her favorite travel moments. they may surprise you.

Sticking to a Budget

Nothing kills a good time quicker than a steep bill at checkout. Marsicano remembers a family trip that coincided with a bout of sleep issues her toddlers were wrangling with, complete with night terrors loud enough to raise the dead—and other guests. “We spent several days, and sleepless nights, with cranky kids,” she says. “If we had spent $10,000 for the trip, I’d be really depressed about the way it turned out.”

Instead of breaking the bank on over-the-top trips or waiting until you have a bigger budget to work with, just aim to keep trips simple. Marsicano recommends renting a condo or apartment with a kitchen, instead of committing to pricey hotels and meals out; traveling off-season, when prices drop; and choosing simple kids’ activities, like bike rides and mini golf, for inexpensive entertainment the whole family will enjoy.

“Traveling together is a marvelous thing,” says Decker. “When my children were small, watching their wonder at giraffes with blue tongues, or the magic of Yellowstone—elks that camped out in front of the post office, closing it down for the afternoon; and puddles that boil—are snippets in time that I will never forget.”

Do you have any memorable family travel moments to share and inspire others? We’d love to hear them!

Photographs by UrbanSitter