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How to Use the Holidays to Plan Your Next Epic Adventure

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What begins as a dream conjured up during casual dinner conversation could become a reality.

Photo by Dmitry Molchonov/Shutterstock

What begins as a dream conjured up during casual dinner conversation could become a reality.

Take advantage of the fact that everyone is gathered around the table to start plotting out where to go together in the coming year.

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Five years ago, Chez Chesak decided to shake things up during the postmeal/predessert lull at his wife’s family’s massive Thanksgiving gathering—he handed out travel catalogs to the dozens of attendees.

“Realizing what a big dynamic group it is, I didn’t want to spring it on them. I laid the groundwork gently,” he said, recalling that he dropped the fact that he was going to bring some travel catalogs into the group emails that were circulating prior to the annual event. “It’s since become kind of a thing. People know it’s coming and they look forward to it.”

Chez Chesak’s family looks through travel brochures during a holiday meal.

Chesak, who is the executive director of the Outdoor Writers Association of America, had observed that while his wife’s large family loved to travel together, there hadn’t always been a proper venue for brainstorming where to go next. So, he decided to try to give the process a little more direction by compiling brochures from tour operators that he felt could serve up some inspiration.  

Now that this new tradition has been engrained, the family has even given it a name—they call it “passing the travel sauce.”

“It’s just a great opportunity to sit down and kind of fantasize about [places to travel to],” said Chesak.

But they do more than just fantasize. Since introducing the new custom, the family has traveled to Central America, China, and Bonaire. This year, Chesak plans on pitching Munich, Germany, to celebrate his 50th birthday in 2020—he was born there but his family moved soon after and he wants to go back.

If you like the idea of starting your own holiday travel planning tradition, here are some tips Chesak offered after several years of ironing out the process.

Research travel companies in advance

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So much of the success of this venture will rely on choosing the right travel inspiration for your friends and family. This means making sure that the tour companies, hotels, cruises, or whatever travel style or destinations you (quite literally) bring to the table have been somewhat vetted. If you or those you know have had positive experiences with certain companies, that’s a great place to start. If you don’t know where to begin, consider engaging a travel agent for recommendations (and to help plan and execute the trip if it turns into something rather involved). Also, think about the dynamic of the group and the travel styles and destinations that would likely be a good fit. Is this a more active crew? Do you need this trip to work with several generations of travelers? You should be presenting ideas that make sense for your audience.

How to Choose the Right Tour Operator for Your Next Epic Trip

Chesak said that for his clan, having the physical brochures on hand really adds to the sharing and community spirit of the experience (even though he admitted that in his day-to-day life he prefers to forgo the physical pamphlets for more eco-friendly e-browsing).

He said, “Having the physical catalog in your hand just makes it so much easier to sit down together and say, ‘Hey, look, I’d never thought about Croatia before but this sounds amazing.' And then you can hand it to the person sitting next to you.”

Chesak and his family recently did a diving trip in Bonaire, a plan that was forged during the holidays.

Make sure to get everyone involved

The key, according to Chesak, is making the process inclusive and democratic. At his family’s holiday table, anyone can introduce any kind of trip, even if it might be out of the price range or scope for individuals or the group. “There’s nothing wrong with having that fantasy for a moment,” he said, adding that pie-in-the-sky dream trips can also turn into ambitious goals. Maybe younger family members with lofty travel visions can establish a fund-raising idea or savings plan, for instance.

“You have to respect their voice,” said Chesak. If someone suggests a travel idea that may seem a bit out there, “at the very least you can say, ‘Oh, let’s talk about that. Why is that adventurous to you? Tell me more,’” he added, offering up a lesson in family diplomacy as much as in group travel planning.

Figure out a path to consensus

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For each family or group of friends, the process of choosing a particular trip will look different. Some families are more easygoing and agreeable, and some might feature stronger personalities that may make it harder to agree. For those worried about how to come to a consensus on a particular trip, Chesak’s crew has come up with a great resolve: Zero in on a landmark event or celebration to help steer the decision-making. Does someone have a big birthday coming up? Perhaps that person gets to decide the next destination or type of trip. Is there a major anniversary on the horizon? Let the lucky couple choose. Or maybe a new grad should pick the next trip. If that doesn’t work, you could always put it to a vote (and even it make it anonymous if need be).

It’s important to remember, it’s OK to “just say no,” said Chesak. If the chosen trip isn’t to someone’s liking, they can simply take a pass.

How to get everyone organized

“It’s never a bad thing to call an agent,” said Chesak, noting that if the travel plans evolve into a more complex trip or constitute a larger group, the help of an experienced travel agent is highly recommended. In his family’s case, “the honor of choosing [the trip] comes with the burden then of becoming kind of a trip leader. And I say burden in quotes.”

What Does a Real Luxury Travel Advisor Do?

Whoever takes the lead, some degree of organization will be required. Present the chosen itinerary, including travel dates, so people can check their budgets and calendars. Then give everyone a deadline for when they either need to commit or decline to join the trip. Depending on if this is a DIY crew or a group that requires more hand-holding, this is the point at which you will want to decide whether the group is going to book all of its own travel or if you want to engage a travel agent for help. If you’ve decided to go with a tour operator, the operator can also serve as a group/trip organizer and help each individual or group within the larger group with their travel plans and bookings.

“It makes things so much easier,” said Chesak, about working with a tour operator that specializes in family or group travel. He added that another benefit of working with tour operators is that they can handle the inquiries group members may have before and during the trip.

“All the questions, all the logistical concerns, heaven forbid something goes wrong, a flight is canceled, luggage is lost, that then is not being dumped on you because it’s your vacation, too,” said Chesak. The tour operator becomes “a shield for you and the focal point of all the weirdness because nobody wants that on them.”

Weirdness aside, he said, just keep an open mind and the epic group trip that you started dreaming up somewhere between the mashed potatoes and the apple pie is much more likely to become a memorable success.

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