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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 together to honor 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, “Ted Lasso” star Jason Sudeikis, 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.”
Sudeikis is hardly alone in her planning of a massive family trip. In fact, two in five travelers invite extended family members on their trips. That's according to the 2025 Hilton Trends Report, which surveyed more than 13,000 adults worldwide in June 2024 who said they planned to travel within the next 12 months.
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.
She's also one of the older members of the family. Hilton data suggests that — for better or for worse — planning tends to fall on people like Sudeikis.
"When it comes to planning, pleasing everyone is not easy," according to Hilton's report. "The multi-generational trip planner, often the matriarch of the family, is increasingly looking for unique, once-in-a-lifetime adventure destinations or experiences to create an enticing option for everyone."
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, Massachusetts, 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.
» Learn more: The best credit card rewards for family travel
Select 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.
Decide 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.
Consider heading to property you already own
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.
“Otherwise, you’d become a travel agent yourself trying to coordinate that,” she says.
Consider resort-style vacation rentals
For families who want the convenience of owned property but don't have access to one, resort-style vacation rental communities offer an attractive middle ground. Properties like Reunion Resort and Golf Club in Kissimmee, Florida, provide the space and amenities of multiple vacation homes while offering hotel-like services and facilities.
At Reunion Resort, families can book everything from three-bedroom condos for smaller groups to massive estates like a 22,000-square-foot mansion that sleeps up to 32 people. The resort's 2,300 acres include three championship golf courses, multiple pools with lazy rivers, tennis courts and six restaurants — meaning there's something for every generation and interest level.
The resort model solves many logistical headaches. Unlike coordinating multiple Airbnb properties, families can book adjacent or nearby vacation rentals within the same community, often through a single booking platform like Marriott's Homes & Villas program. Plus, the resort offers concierge services and on-site maintenance, eliminating the host reliability issues that can plague individual vacation rentals.
Don't overlook all-inclusives
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.
All-inclusive properties are also massively growing as of late, particularly among big hotel chains that run loyalty programs. For example, in early 2025, Hyatt Hotels announced plans to acquire Playa, which is a leading operator of all-inclusive resorts in Mexico, the Dominican Republic and Jamaica.
That's good news, as travelers can earn and redeem World of Hyatt points for those stays.
Also in 2025, Marriott International expanded its luxury all-inclusive properties under the All-Inclusive by Marriott Bonvoy portfolio. With that, Marriott International plans to integrate certain luxury brands such as JW Marriott and The Ritz-Carlton into its all-inclusive portfolio. Other recent additions included Almare and Paraiso de la Bonita (both part of The Luxury Collection in Mexico).
Minimize planning with specialized programs
Hotel chains are also launching specialized programs for multigenerational families.
For example, Hyatt's expanded "Roots to Reunion" program, available at 10 Destination by Hyatt properties from California to the United Kingdom, offers dedicated staff called "Family Travel Experts" who work one-on-one with families to curate itineraries for different ages and interests. Properties like Cheyenne Mountain Resort in Colorado Springs provide "Reunion Ready Kits" with items like s'mores ingredients, while Hotel X Toronto offers in-room robes and slippers for all sizes and on-site strollers for lakeside walks.
Plan meals and activities
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.
As far as activities, plan a mix of things people can do on their own (after all, sometimes a break from family is the best part of a family reunion) and create activities people can do together.
You might offer optional activities, like physical activities for the more athletic family members, or wine tasting for the adults.
But, bake in time for everyone to come together. Appointing a family member to lead a family-themed trivia can incite lots of laughs, and people of all ages and abilities can participate.
Decide how to pay 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.
» Learn more: Secrets to family travel on a budget
Make 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 colorful 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.”
Find out how I planned my own family reunion vacation in the latest episode of the Smart Travel podcast.
This article was written by NerdWallet and was originally published by The Associated Press.
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