For the past 11 years, Kathy Sudeikis has planned a yearly family reunion. Called “Nanapalooza,” the tradition began as a way to bring her six siblings and their families – including “Ted Lasso” star Jason Sudeikis – together to honour the memory of their mother.

Held annually near Michigan City, Indiana, the event has doubled from about 40 people in its first year to 74 in attendance last summer. Kathy’s son Jason ranks among those who have never missed a year of Nanapalooza – and he’s not the only one who’s committed to participating.

“One family drives from New York so they can have their car with them,” Kathy Sudeikis says. “Another cousin had her baby induced so she could bring the baby to Nanapalooza.”

Planning a multigenerational trip

Kathy Sudeikis works for Acendas Travel, a Kansas City area-based travel management company, so she has extensive experience in the industry and is the de facto leader of Nanapalooza. But unlike Nanapalooza, not all multigenerational trips and reunions go well.

For instance, some families could end up picking up a tab for more than what they owe, or have clean-up duty daily versus a rotation. Arguments can erupt over details such as when to travel and how to split bills. That’s why Heidi Durflinger, president of EF Go Ahead Tours in Cambridge, Mass., recommends hiring a tour director.

“The tour director is there from start to finish, so they get to know everyone’s interests,” Durflinger says. “They’re pros at handling group dynamics.”

You can also, of course, plan it on your own.

Selecting dates

Sometimes, the hardest part of trip planning can be settling on dates. “It’s just never going to work perfectly for everyone,” Kathy Sudeikis says. “There’s always someone whose kid has band camp that week.”

To avoid such drama, Kathy Sudeikis advises tying trips to important family dates. With Nanapalooza, it’s the anniversary of the death of their mother. Otherwise, Kathy Sudeikis recommends simply committing to the date.

Deciding where to go

To help agree on a location, Durflinger recommends considering family heritage. Her company recently organized a family reunion in an Italian village where the family’s ancestors were from.

Nanapalooza’s location, meanwhile, was selected because one family owns a waterfront property on Lake Michigan, which provides a convenient base for most meals and activities. The families book their lodging nearby.

On any extended family vacation, Kathy Sudeikis recommends that each family unit is responsible for booking their lodging and transportation.

Planning meals and activities

Cruises or all-inclusive resorts can simplify family vacations by offering meals and planning activities for everyone. For example, at Vista Verde Guest Ranch, an all-inclusive dude ranch in Clark, Colorado, guests choose activities from a pre-selected list, then everyone regroups in the main lodge for meals. Active folk might choose tubing or snowshoeing, while those seeking a more relaxed itinerary might opt for sleigh rides or wine tasting.

Kathy Sudeikis sends out a food chart in advance to reunion attendees. Then, each of the seven siblings picks a single meal to prepare for the entire group. “Everyone can do their own thing during the day and then meet up for dinner,” she says.

Paying for the trip

At Nanapalooza, each family rotates supplying the entire group’s dinner. Frugal families could cook, while another family might pay for takeout. The lakeside location of Nanapalooza keeps activity costs low.

Though Nanapalooza is fortunate to have minimal financial disagreements, that’s not always the case with other family trips. Kathy Sudeikis recommends cruises because families have options for staterooms, depending on their budget.

“Make it work for all your siblings because they might not all be in the same financial brackets,” she says.

And don’t overlook a professionally organized tour. Durflinger says a tour may come out cheaper since they can secure discounted rates for large groups.

Making it memorable

Every Nanapalooza involves some sort of tchotchke to commemorate the trip. In 2021, it was a unique hoodie. Earlier that year, Jason Sudeikis won a Golden Globes for his role in “Ted Lasso.”

Because the awards ceremony occurred near the height of the COVID-19 pandemic, he accepted his award virtually while wearing a tie-dyed hoodie. The colourful covering, created by his sister, sold out quickly after his acceptance speech.

Every attendee at Nanapalooza in 2021 got one.

“She ordered 80 hoodies for us all that year,” Kathy Sudeikis says. “It shows just how everyone is committed to this in Nana’s spirit.”