How to Plan a Family Vacation Where Everyone Feels Safe During COVID-19

Every traveler knows the feeling of desperately needing someone to turn to. It's not just on the road—deciding where to go for your first international trip or how to balance solo travel as a new mother can be just as challenging. In our new Women Who Travel advice column, we'll be answering questions from our Facebook group members, readers, podcast listeners, newsletter subscribers, and travelers. Have a question? We'd love to hear from you. Email us at womenwhotravel@cntraveler.com.

Dear Women Who Travel,

My family plans a big trip together every summer—we usually meet up somewhere and rent a house, with a few generations (adult siblings and their families, plus our parents). This year it's obviously more complicated.

We halted planning our trip when the pandemic hit, but now it seems like some form of summer travel is on the table and the conversation has restarted. The real sticking point, however, is that everyone is on totally different pages. Some family members, all of whom are younger and have no underlying conditions, aren't too fazed about a long car drive and getting together in one house. My mother (who is over 65) doesn't want to miss out and says she'll do whatever we decide—but I can't tell how comfortable she actually is with the whole idea. One of my siblings says they need everyone to quarantine for 2 weeks if we're going to do it—but I'm not sure everyone will seriously commit to doing so.

How are we supposed to find middle ground? And how can we make sure that whatever we do works for everyone's comfort level (and safety)?

—A very cautious traveler

Dear Cautious Traveler,

Your question is basically the song of the summer: everyone is asking the same thing. With cities slowly opening up, the opportunity to take a road trip or rent a house is suddenly an option for some people, but actually putting together a trip—and one that your entire family can feel great about—is much more complex.

I'm still hunkering down in my little apartment, totally intimidated by summer travel planning as well, so I tapped a couple of other women to get us both some answers: Marissa Moore, a family therapist and founder of Therapy Brooklyn in New York's Greenpoint neighborhood, and fellow Condé Nast Traveler editor, Corina Quinn, who was the first person on our team to tackle the multi-generational family trip this summer, and learned quite a bit through the process.

In addition to the obvious baseline advice—to follow all local regulations and always check the Centers for Disease Control (CDC) website before making travel plans—they had a ton of tips. First, they both emphatically agreed on one key factor for planning and executing a harmonious family trip right now: communication.

"As we finally venture out, this is what everyone is navigating this coming summer," says Moore. "But it's [still] a highly anxious time. Get orientated toward why this vacation matters to everyone [in your family]. When you ground the conversation in that, you have common ground to start on."

Moore suggests setting up a group video call right as you begin discussing a trip and block off an hour when everyone can hop on and give the conversation their full attention (in other words, don't leave Zoom open while you simultaneously prep dinner). Having conversations in the family group text, on the other hand, leaves room for misinterpretation, and for side conversations and he-said-she-said dialogues. Rather than creating space for drama and hurt feelings, get everyone in the same "room" to lay the groundwork as a team.

Give everyone time to say what's on their mind: One sibling might say that they need assurance that everyone will quarantine for two weeks; someone else might ask everyone to get a COVID-19 test before embarking. It's important to acknowledge that everyone has different risk tolerance levels right now—and that that's okay.

If you think that a member of the family (like your mom) is having trouble voicing their opinion or speaking up, Moore suggests directing questions their way once everyone has spoken. You can even offer multiple choice answers to draw a response out, like "Is this trip sounding safe to you, would you be interested in discussing more safety measures, or does it feel outside of your comfort zone?"

For Quinn's family, everyone chose to lead by example as a means of asking for what they needed. "We're a group of eight adults and six kids, and everyone has had different situations over the past few months," says Quinn. "The way our family operates is to volunteer our positions." Each began by honestly sharing what life has looked liked during quarantine for them, and what precautions they've been taking. Quinn, for example, has been working from home in New York City for months, while the rest of the family is Northern Virginia, and has only seen one other person. She also volunteered to make an appointment with her primary care doctor to get a professional opinion on the trip.

"Everyone appreciated that I volunteered to go to my doctor, and then they followed [suit]," says Quinn. "I don't think any of us felt comfortable telling someone else what they needed to do, so we volunteered instead." Ultimately, everyone ended up seeing their doctor for advice, once they agreed that they would all drive to the home they rented in North Carolina's Emerald Isle. Her brother even shared reading material on how to safely expand your bubble that helped put everyone at ease. (They also decided to bring their own groceries, took temperatures the week before the trip, and carefully plotted the rest stops they'd link up at, sanitizer in hand, along the way.)

Once guidelines have been set, both Quinn and Moore emphasize that recurring check-ins leading up to the trip are also essential—as is keeping the lines of communication open once you arrive at your destination. Sharing updates on tests, for example, can help everyone feel like these measures are being taken seriously. It also gives family members a chance to voice concerns as they bubble up.

If you feel like someone isn't holding up their end of the bargain, Moore suggests being mindful in how you address concerns, and check defensiveness when you can. "People might want to be called out in different ways, so establish ways to check in during the trip to set the expectation that you'll keep talking about [how things are going]," says Moore, who suggests touching base nightly as a possible routine. "To compassionately call someone out, lead with your emotional impact, what you're needing, and ask questions." At a time when all of our anxieties are at the forefront, shut down the instinct to make assumptions about why someone is acting the way they are.

Luckily for Quinn's family, the need to confront each other didn't happen on their trip. But she says that having every family member focus on the advice offered by their doctor, helped establish an understanding that everyone was doing what best for them. Ultimately, though, being with family meant that everyone kept each other's best interests in mind. "Nobody wants to be the person who knowingly infects everyone else," says Quinn. "Prioritizing those conversations, and being open, laid a nice foundation that made it possible to do the trip." She says that getting to be together after months in isolation was well worth the prep work, and countless conversations, it took.

If everyone in your family is bought into the idea of being together, then you can certainly make something happen. Maybe it looks like everyone driving to your mom and renting a home near where she lives, so she doesn't have to travel; maybe it looks like renting a few separate apartments in one place, with socially distanced hangs during the day. But it all relies on being open, and ultimately, trusting one another. If those two things are too great of a roadblock right now, maybe focus everyone's energy on planning ahead for a great winter trip, instead. It'll give your family more time to get comfortable with the idea of travel, and to touch base on what will make them feel safe. That light at the end of the tunnel will certainly help you get you through summer.

— Women Who Travel