Happy travels to you: How to plan a family vacation that everyone will enjoy

I can count on zero fingers the number of times my father consulted me about where we vacationed or what was on our itinerary. When I was a child, he was in charge of travel; my mother, younger sister and I were simply along for the ride. Though we journeyed to some amazing destinations – including South Pacific islands, the Azores, Amazon rainforests and the Caribbean – the activities were Dad-centric, which meant fishing was always on the itinerary. Great for Dad, not so much for the rest of us, who had no interest in spending our days at sea pursuing marlin or learning the intricacies of fly-fishing.

Although I have come to appreciate fishing as an adult, it’s not a passion my wife or 9-year-old son share. When we began traveling together nearly a decade ago, I resolved to be a different kind of vacation planner, with an emphasis on the “we” rather than the “me.” It became my goal to design itineraries that engage all of us on multiple levels throughout the journey. This approach takes extra work and some delicate negotiating skills, but it is always worth it. We look forward to our trips and return with great memories, eager to travel together again. Here are some tips, based on my experiences and discussions with travel experts.

Longer isn’t necessarily better. There is an expiration date on some vacations. The larger the group and the more generations involved, the shorter it should probably be. “I don’t want to be with that many people for too long,” says Tykesha Burton, who writes about culture-focused family travel on her blog Momma Wanderlust. “Seven to 10 days max. After that, it’s all too much.” However, when she travels with only her husband and their two young children, she doesn’t think there are time limits – except those set by their school and work schedules.

Consider everyone. The first question a trip planner needs to ask is whether a destination will be fulfilling for the entire family. If it’s a one-note place mostly catering to a single activity or sensibility, it’s not the best idea to drag everyone there. Save that trip for a solo adventure. While a spot doesn’t need to be stereotypically kid-friendly – such as Disneyland or Hershey, Pa. – it does need to offer elements that will appeal to the younger set. And keep your partner’s interests in mind, too.

Make a group decision. Once children are old enough to have strong ideas about travel, ask everyone to suggest a couple of places that interest them, then whittle down the list to the ones with the broadest appeal for your family. From there, either everyone can vote, or you can make the decision based on other important factors, such as budget and whether the destination will truly shine at the time of year you plan to visit. The process will give everyone a sense of ownership even if their destination isn’t chosen.

Space is key. Although it might be nice to save money by squeezing as many people as possible into the most affordable housing option, a little extra room makes a big difference. Giving everyone their own area to decompress and enjoy downtime alone helps mend moods and keep vacationers energized. Leveling up to larger lodgings might mean renting an Airbnb instead of a hotel room, but that can have the added benefit of a kitchen, which can help you trim your food costs and cut down on mealtime stress.

Bring a bag of tricks. Pack goodies to take the edge off travel’s smaller aggravations. Burton always has snacks on hand to prevent her children from getting hangry and gum to help them pop their ears when flying. She also brings a bag full of toys from the dollar store. “It doesn’t matter that it’s a dollar. It only matters that it’s new, and they’ve never seen it,” she says. “It keeps their attention long enough that they aren’t bored for a while.”

Be realistic at mealtime. Travel is a great opportunity to expand your child’s palate, so hit a few restaurants showcasing the region’s food. But if you have picky eaters, make sure the menu also includes some classic kid fare. “There has to be chicken nuggets and fries,” Burton says, “but I always order one thing that’s new and different for them to try.”

Discover the unique. “Don’t look for things you can find near you, like zoos or amusement parks,” says Tamara Gruber, founder of the family-travel-focused website We3Travel. She suggests seeking out experiences unique to your destination that will be entertaining and educational. Travel can be a great way to broaden your children’s minds, so don’t miss these opportunities for enrichment. This might mean taking an art class tied to the area’s culture, hiking to a one-of-a-kind outdoor feature or booking a guide to give you a deep-dive tour of a singular aspect of the place such as a historical neighborhood or regional cuisine.

Have fun together. Book a few group activities with mass appeal. “What really makes vacations are the experiential things you do together as a family,” says Amie O’Shaughnessy, chief executive of Ciao Bambino, a family-focused travel agency. “Immersive activities that are more structured can make the best memories.” This could mean a horse-riding excursion, ziplining adventure course or cooking class.

Let each person choose something. Allow every family member to pick one activity that will be their special moment on the trip or have them schedule a day. Be warned: A child’s choice might force parents out of their comfort zones. “I’ve done many things that frighten me to death for my daughter because it’s something she wants to do,” Gruber says. “We’ve gone whitewater rafting, and I have a fear of water. But it’s a bonding and learning experience.”

Accommodate both travelers and vacationers. These are totally different mindsets. One wants to do everything; one wants to do nothing. “I’m definitely a hit-the-ground-running, go-and-see-everything type,” Burton says. “My husband is not.” To strike a balance that accommodates them both, she always plans a day of chillaxing after a busy day of excursions or events.

Say yes to babysitting. Before the pandemic, many parents felt as if they didn’t have enough time with their children, so they often didn’t want to be apart from them on vacation. Now, most families feel as if they have had too much time together, so some separation can be a great benefit to a trip. Many resorts and hotels offer children’s clubs or other independent activities for kids, although travelers should expect to pay for them.

Don’t overschedule. There’s nothing worse than waking up on a vacation and realizing every minute of the day is jammed. An endless litany of meal reservations, guided tours and timed museum visits can make even the adults cranky. Don’t start your itinerary at the crack of dawn, which is not ideal for late-rising teens or smaller children who want time to play before getting in the car. “Leave some downtime, some unplanned time, some time to explore and uncover,” O’Shaughnessy says. “At the end of the day, that unknown is the essence of the joy of travel.”

Stay flexible. Your travel itinerary will not unfold exactly as you planned, especially with the pandemic still disrupting life around the world. Things are going to go wrong be it a delayed flight, canceled tour or unexpected restaurant closure. “Have the expectation that it isn’t going to be perfect,” O’Shaughnessy says. “But remind everyone, ‘We’re getting out, and we’re doing something, and just that is so enjoyable.’ ” Parents should go with the flow and remain as calm as possible; this will set the mood for the whole family. Don’t get all huffy and yell at the airline attendant, customer service rep or hostess. Don’t dwell on what you’re missing; instead, figure out viable alternatives, stay positive, and embrace the unknown. After all, travel is an adventure.

Understand the risks. If you decide to leave the country for your vacation, everyone must be comfortable with the potential ramifications if someone tests positive for the coronavirus. This will probably involve a longer stay in the country you’re visiting, along with quarantining, missing work and school and added costs. If these risks don’t work for the family, don’t leave the country.

Keep an eye on the future. “I want to make sure my family wants to go on the next vacation, which means they have to have a good time on this vacation,” Gruber says. Really listen to your family throughout the process – from the moment you start considering a trip until the moment you come home. If you have their buy-in, the journey becomes a cooperative partnership, which is the secret to being a successful family no matter where you are in the world.