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Multigenerational Holiday Gatherings Reimagined

Whether you book a trip or stay home, explore new ways to connect with the whole family

multi-generational family playing on the beach

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Thanksgiving is officially in the (family) history books. And you know what that means: It is time to look ahead to the next celebration on the horizon.

If gathering at home for the holidays has become a challenge because your house is too small for the entire family or you’re scattered across the country and there’s no central place that makes sense, there are still plenty of ways to gather together for Hanukkah, Christmas or New Year's, even if you’re planning at the last minute.

Consider renting a ski house, beach house or rooms at a B&B, or travel to a nearby city to share the sights you love with the next generation. It’s not too late to book a cruise or a trip abroad to experience another country’s holiday traditions.

Holiday travel is a “great opportunity to connect and reconnect with family members on a different level than when you are at home,” says Julie Danziger, a travel adviser at Ovation Travel Group. “There are minimal distractions and you can really enjoy each other’s company. When you’re home, a lot of people lose that.”

The key to a multigenerational family trip, especially when planning late, is to be flexible and open to new experiences, since prime vacation spots like resorts in the Caribbean are booked far in advance, and prices for popular spots can become out of reach. To get the best airfare, consider traveling on the actual holiday and be flexible about when you return, says a spokesman for United Airlines.

Here are suggestions to please everyone from your parents to your 5-year-old grandchild:

Rent a house

Airbnb, with 5 million rentals worldwide at all price levels, is a great place to start, but it’s worth checking out home rental companies that offer hotel services, Danziger says. Onefinestay and Oasis feature luxury properties in destinations from Mykonos to

grandparents watching grandchild play in the snow

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Manhattan complete with concierge services. Your best bet is to pick a location that caters mostly to business travelers, since there is likely to be good availability during the holidays.

Take a cruise

A cruise is a great choice for multigenerational holiday travel, says travel expert Wendy Perrin of “Cruises make everybody in the family happy. The grandparents can sit and watch the grandkids run around them on the deck. Everyone can do what they want to do at their own pace, and then get together for dinner at night.”

Perrin recommends using a cruise expert such as CruiseCenter to book a trip that meets your family’s various needs, versus sorting through a flurry of confusing last-minute travel deals online. Holland America has eight ships cruising the Caribbean for the holidays for trips lasting three to 15 days, and there was still some availability, a spokeswoman said. Each ship has special activities for children and teens, and all stop at Half Moon Cay in the Bahamas, the company’s private island, which boasts a new water park.

Holiday travel is a “great opportunity to connect and reconnect with family members on a different level than when you are at home.”  

— Julie Danziger, a travel adviser at Ovation Travel Group

Explore a new city

Two generations of the Danziger family are celebrating Hanukkah in Puerto Rico, and four generations plan to travel to the Bahamas after New Year's, made easier with school breaks and grandparents living in Miami. Cities offer a chance to sightsee, enjoy the cuisine and even take in a sporting event. “Consider taking a trip to a place that is not in season but is still wonderful like a European city or a city in the U.S. like Nashville, Charleston, Chicago or Austin,” Danziger says. “It’s a great opportunity to visit: They’re a good value off-season, but they’re still wonderful places to explore.”

New Orleans is celebrating its 300th anniversary this year. A multigenerational visit could include the National World War II Museum — a great spark to share your family history. The museum is offering a Teddy Bear Tea with a visit from Santa, plus performances of holiday favorites by the group Victory Belles.

Stay home

If a getaway doesn’t work for your family because of schedules or finances, think about new ways to connect with each other. Baking together can be a satisfying way to do that, says Vallery Lomas, winner of Season 3 of ABC’s Great American Baking Show, who travels home to Baton Rouge, La. “We keep our heritage alive by preparing family heirloom recipes by the amazing women in my family who have passed on,” she says. “We try to balance our time in the kitchen with other favorites like Scrabble and seeing a Christmas Day new release.”

Another thing to consider: doing a new multigenerational activity such as volunteering at a food pantry. Feeding America, the nation’s largest domestic hunger relief organization, has a food bank locator on its website. After all, holidays are all about giving, and there can be great joy in giving back.

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