9 ways to bring every generation but leave the family drama at home

Bookings for three-generation travel shot up beginning last year, said Franziska Wirth, the director of sales and partnerships at Insight Guides, which connects travelers with local travel advisers. “In 2021 we had a lot of inquiries but not that many bookings,” she said. Now, she said, “the over-65 crowd is coming back, and they are bringing their families.”

As multigenerational travel roars back, so does a tricky topic: money — who is paying for flights, lodging, meals and activities, and how luxurious those aspects will be.

It’s important to understand the amount that family members can and want to pay for a group vacation, said Arleta Cosby, the chief executive of Cosby Travel Consultants, a travel agency in Virginia. “If you just present a plan, some will opt out due to cost,” she said, and might even be too embarrassed to disclose their discomfort, so there’s little chance of addressing it for the next trip. The most important thing, her clients tell her, is to “be inclusive,” she said, so she suggests booking less-fancy places that everyone can afford.

Thinking about getting the whole extended family together to make up for lost time? Here are nine tips:

Start planning at least six months in advance

Coordinating school and work vacations for multiple branches of a family and creating an inclusive itinerary should start about half a year before the trip, said Wirth of Insight Guides. A professional travel agent can make suggestions, track details and manage communications, she said.

You don’t have to book, or fly, together

Groups of 10 or more may find discounted airfares, but those often come with significant change restrictions, said Ellen Regenstreif, a travel adviser who plans multigenerational trips for ProTravel International, in Beverly Hills, California. It’s usually easier for each family branch to make its own reservations, she said. As for the sticky question of who sits where, Regenstreif counsels grandparents who want to fly business class that it’s OK if the whole clan isn’t with them at the front of the plane.

Schedule activities all can join

Riding in a van with a guide and a driver for sightseeing may be easier than taking a walking tour on cobblestone streets. Elders may enjoy family time poolside or watching kids take surfing lessons if they can’t join in. “If grandma sleeps late, plan energetic activities in the morning and then come back and collect her,” Regenstreif said.

Don’t try to see too much

Scheduling one day of leisure for every three days of activity can give elders a chance to recharge and give young kids some downtime “just to play in the hotel room,” Wirth said. She also suggests spending more time at fewer places rather than aiming to see every city and site because “six-hour car rides usually aren’t fun for anyone.”

Free time matters

“You don’t all need to be doing the same things at all times,” said Fine, who has gone on more than 20 vacations with her extended family. She has found that “a mix lets people spend time together but also do what’s important to them.” Young children may get cranky in the afternoon and need a nap. So may some adults. Teens may want to shop rather than tour another museum. Some families segment the day with a group activity in the morning, free time in the afternoon and then a group dinner.

Cooking’s cheaper, but dining out is special

Cooking together can save on dining costs and avoid the hassle of making reservations and arranging group transportation, but staying in every night might make the experience less of a vacation, Regenstreif said. “Experiencing the food culture and interacting with people is part of the experience,” when traveling, she said. A hybrid approach of some cooking and some dining out usually works, she said. Also consider varying your dinner companions, Fine said: “You don’t all have to eat together every night.” The younger generation may want to venture out on their own, or grandparents may want time alone with the grandchildren.

Discuss sharing costs and remember to say thank you

If one branch of the family, or grandparents, are picking up the tab, Regenstreif suggests that each part of the group pay for dinner one night, buy snacks on a tour day or find another way to say thank you. When costs are being shared more widely, the family should discuss how finances will be handled in advance, she said, “and do it in whatever way is comfortable for the group,” whether that is taking turns making grocery runs or keeping a more detailed spreadsheet of who’s been paying for what.

Be mindful of health concerns

For minor illnesses, be sure to pack basic medical supplies like a thermometer, a pulse oximeter, disposable masks, COVID self-tests and over-the-counter symptom relievers like cough medicine, said Rebecca Acosta, a nurse in Manhattan whose Traveler’s Medical Service helps people prepare for trips. If any family members come down with COVID or another contagious bug, the advice is the same as at home, Acosta said: Isolate sick people if possible, treat their symptoms, and ask them to wear masks in shared spaces. If they are having trouble breathing or experiencing other serious symptoms, take them to an emergency room, and if they have a significant preexisting condition, check in with their home physicians, Acosta said. To keep the rest of the family healthy, open the windows to increase fresh air and move activities outside if possible. You’re still on vacation, so “try to set things up so you can avoid risk but keep enjoying yourselves,” Acosta said.

Make space for everyone

Each family has its own needs when it comes to lodging. A common kitchen or hangout area may be a high priority for teenage cousins, while families with young children may want separate spaces so they don’t have to worry about making too much early-morning noise. There’s a price range for every lodging category, and it’s important to weigh the trade-offs, Regenstreif said: “When you go for a lower price, you may be giving up on location, amenities, size, or other important factors.”

When choosing a destination, think about the aspects of the family that need the most attention, Regenstreif said. Accessibility issues may be important. Alvaro Silberstein, a co-founder of Wheel the World, which specializes in accessible travel, advises those with medical or mobility needs to keep medications handy (not in their checked luggage), reserve airport wheelchairs in advance, and make sure lodging offers elevators or ramps and showers with grab bars.

And don’t forget that some family members, for example those who identify as LGBTQ or those in an interracial relationship, may not feel comfortable in certain destinations. “The goal is to pick a place everyone can be themselves,” Regenstreif said. “Making a trip beautiful is to respond to each person’s needs but also create a dynamic that works for everyone.”

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