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Plan Multi-generational Family Vacations Without the Stress

Big-group vacations are all the rage

spinner image families taking vacations together
Six families share their tips for planning large multigenerational vacations.
Courtesy Debbi Breeling / Courtesy Cathy Harney / Maria Kandalova / Courtesy Jenny Gillett / Courtesy Monique Walters / Courtesy Patti Acheson / Getty

Domestic family or multi-generational travel is a priority for travelers 50-plus in 2023, according to AARP research. The annual AARP Travel Trends study found that 14 percent of travelers expected to go on multi-generational trips. With so many ages and needs to consider on such trips, how do you plan an unforgettable and low-drama vacation involving multiple families or friends and maintain your sanity (without going broke)? These six families show us how it’s done.

The classic giant beach house confab

spinner image the oransky family rented a beachfront house in corolla north carolina
The Oransky family rents a beachfront house in Corolla, North Carolina, in the Outer Banks.
John Greim/Arcangel / Maria Kandalova

Destination: Corolla, North Carolina

Number of travelers: 18 to 20

Trip organizer: Charles Oransky, age 72

We’ve been going to the Outer Banks (OBX) since the mid-1980s. Back then, it was just my wife and me and our four children. Now each child is married, and we have eight grandchildren. Sometimes a friend or two join us too.

We’ve always gotten a beachfront house (usually through Twiddy & Company), and as we’ve grown in size, our house needs have grown. The one we had last time seemed to have two of everything: two refrigerators, two freezers and two stoves, and a separate kitchen on a different floor. We used them all.

The great thing about a house as opposed to a hotel is if you have little children, they can run around and be free. Sure, there are challenges. People are on different schedules and vacation differently. The really young children make a lot of noise. But you can always find your own place. You can go sit down on the beach. You can sit by the pool.

I have several favorite times of day. I get up early, and we’ll take some of the little kids to the beach around 6:30 or 7, as the sun comes up. And then we go buy bagels. And dinner is great, because everybody’s at the table. It’s a lot of work to put together, but it’s an amazing experience for all of us. Most of our friends, once their kids are in their 40s, they don’t go on vacations with them. But for us, this trip is a tradition. Every­body loves it. We talk about it all year. When we go away together, there are so many precious moments — the little moments that you can’t plan.

Beach house tips

Rent a year in advance. “When we leave, we book the house for the next year,” Oransky says. Yes, demand is that high.

Try staying for more than a week. “With this many people, it takes a few days to get in the groove,” Oransky says.

Be meal smart. Schedule one big food shop on day one, bring supplies from home, rotate cooking and cleaning, make dinner each day’s one group meal and skip the restaurants, Oransky advises.



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Tent and RV rendezvous

spinner image the acheson family on a camping trip in gunnison county colorado
Patti Acheson and her family camp in Gunnison County, Colorado, where she says the campfires at night are the best moments.
Courtesy Patti Acheson

Destination: Gunnison County, Colorado

Number of family members: 40-plus

Trip organizer: Patti Acheson, age 72

My nine brothers and sisters and I were raised on a farm in Louisiana, so we love the outdoors. As we got older, we all wanted our kids to know their heritage. So we started to have yearly get-togethers. My sister Debbie and I manage the planning. We have a family Facebook group, and we use that to get input. Once we choose a campground, Deb and I prepare a menu for each meal. We post it, and everybody signs up for food, meal prep and cleanup.

The best moments are the campfires at night. We’ll sing and tell stories. I now know family I would never have had the chance to be close to. And we have so much fun.

Camping tips

Be budget sensitive. A plan to print T-shirts ended when it turned out one family would need to buy eight. “We try to do stuff that doesn’t cost a lot,” Acheson says.

Rent a group campsite. It’s cost-effective, and it’s better for campers who aren’t part of your group. Book a covered pavilion to serve as the kitchen and gathering place.

The family dream cruise

spinner image the gillett family took a vacation on an alaskan cruise
The Gillett family cruise to Alaska was delayed twice because of COVID. Each time they rebooked, they upgraded their accommodations.
Courtesy Holland American / Courtesy Jenny Gillett

Destination: Alaska

Number of travelers: 22

Trip organizer: Jenny Gillett, age 45

My grandma always wanted to take the whole family on a cruise, but my grandpa wouldn’t go for it. When they passed away, my dad said, “OK, we’re gonna do what Grandma wanted.” And so we went on a cruise.

The 22 people included my mom and dad, all of us six kids, our spouses (except one who couldn’t go) and our children. The cruise got delayed twice because of COVID, and each time we rebooked, we upgraded. We ended up with eight connected balcony rooms, so the kids could run and play in between the rooms.

If you’ve never planned a cruise, step one is to talk with a cruise line consultant. They save you so much work. My top challenge was making sure everybody had the needed documents to get on and off the ship. For most of us, seeing the Hubbard Glacier was the high point.

Two years of being apart due to COVID had caused some cracks in our relationships. That week on the ship, being together and just having a good time, we repaired those cracks. And I think my grandma would have been really happy about that.

Family cruise tips

  • Have one negotiator. “When talking to the consultant, I asked everybody’s questions,” Gillett says.
  • Choose one rep for each family. That, too, prevents communication overload and simplifies planning.
  • Research the medical services. The boat’s medical staff proved heroic during one heart-health scare.
  • Consider a smaller ship. Some Alaska ships carry 4,000 people. The Gilletts opted for one half that size.

A four-generation Disney blowout

spinner image the breeling family took a trip to disney world in orlando florida
Debbi Breeling used a travel agent for her family trip to Disney World in Orlando, Florida.
Courtesy Debbi Breeling

Destination: Disney World, Orlando, Florida

Number of travelers: 9

Trip organizer: Debbi Breeling, age 62

We started saving for this trip several years ago, and my husband and I paid for everyone: my mother, two of our three children, their spouses and two grandchildren.

Walt Disney World is complex. There are different types of tickets; you can’t just show up. We hired a travel agent, Lauren Cardinale, just to help us navigate the park.

We all installed the Disney World app on our phones, and Lauren linked them together, so one person could make reservations for all of us. It also had a GPS map so we could find our way around.

The whole trip was eight days. My grandchildren loved things like lunch at Beast’s Castle, but I was thrilled they could spend time with my mother. It’s true what they say: Theme parks are fun for kids and adults.

Amusement park tips

  • Hire an authorized Disney vacation planner. They have access to insider info including crowd sizes and program changes.
  • Get off-site lodging. Accommodations for 10 or more are limited within the park. Demand is high: Book a year in advance.
  • Plan some days off. Breeling scheduled free days between park visits, so the family could catch their collective breath.


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The all-inclusive beach resort vow renewal

spinner image the harney family on a trip to turks and caicos
The group vacation turned into a vow renewal for Cathy and Brian Harney in Turks and Caicos.
Courtesy Cathy Harney

Destination: Turks and Caicos

Number of travelers: 14

Trip organizer: Cathy Harney, age 66

When we talked about going on a group trip of about seven days, I wasn’t thinking about our 40th wedding anniversary. We knew we wanted to go to the Caribbean, but we’d never planned for a group this big, and some of our friends and family would be coming from different cities. My daughter and son are good at organizing vacations, but my daughter said, “This is too much.”

My daughter had worked before with a travel agent, Sheila Cannon of Carefree Romantic Vacations, and Sheila came up with a Beaches resort in Turks and Caicos Islands (TCI). She was enormously helpful.

My husband, Brian, knew nothing about the trip. He gets anxiety about traveling, so I have to “kidnap” him, as we like to put it.

First, I put his pressure socks on him, which we always wear on flights. That’s the signal. I then told him we were flying to Turks and Caicos, and we left that very day.

I let on that our daughter and son would be there, but not our best friends or some of the other family. We arrived and got our welcoming drink at the resort, and then friends and family started sneaking in. He was overwhelmed. Happily overwhelmed.

Because we’d recently had COVID, we arrived in Turks and Caicos a few days later than everyone else. I didn’t know it, but Sheila had told my daughter that the resort offers free wedding ceremonies when you book three nights or more. One day we were outside and a young lady gave me a beautiful set of orchids and my husband a corsage, and we turned and saw all these chairs with a gazebo, and all of our family and friends, and I thought, Aha — my children tricked me.

We then renewed our vows for our 40th anniversary, and we sat in the gazebo on a tiny hill, looking out at the ocean with hors d’oeuvres and champagne.

Big resort tips

  • Check child policies. One family wanted to stay at a Sandals resort but discovered it was adults only. If your group includes children, make sure you only book family-friendly resorts. Some all-inclusive resorts even let the kiddies stay free of charge.
  • Ask about free rooms. Sandals and Beaches resorts offer a free sixth or 12th room to large groups that stay a minimum of three nights (blackout dates apply).
  • Spend time apart. With so many ages and interests, leave time for everyone to explore their own vibe. Harney’s group rarely ate breakfast or lunch together, for example, but always met for dinner.
  • Avoid claustrophobia. Many resorts only offer individual rooms, but some have multi-bedroom suites or cabins. Ask attendees before you book; not everyone wants that level of togetherness.


A bucket list multi-gen honeymoon

spinner image the waters and williams family on a group honeymoon in senegal and lamantin resort where they stayed
Monique Waters and Norris Williams invited parents, aunts, uncles, nephews and close friends for their honeymoon trip to Senegal.
Courtesy Monique Waters / Courtesy Lamantin Beach Resort & Spa

Destination: Senegal

Number of travelers: 14

Trip organizers: Monique Waters, age 37, and Norris Williams, age 36

Waters: As we researched this trip shortly after we got married, we kept thinking, What about Africa? What if friends and family came with us? So we invited aunts, uncles, parents, nephews and close friends, and we went on a nine-day trip to Senegal. We didn’t have the experience to organize it ourselves, but my research led us to Henderson Travel Service, the first Black travel agency in the U.S. We had conversations about what we wanted to explore, whether it was art and dancing or even tribal affiliations. They took our feedback and curated a tailor-made trip.

Williams: For my mother, going to Africa was a longtime dream. She said she felt profound joy, love, gratitude and peace there. For me, it was less about the activities and more about watching the family bond. We built a village around each other. It was transformative for all of us.

Multi-gen honeymoon tips

  • Ask first. Waters and Williams sent an online survey asking for everyone’s interests, concerns and questions.
  • Centralize info. The couple built a website that detailed costs, itinerary, hotels, vaccine requirements and more.
  • Spread out the payments. Rather than asking for a lump sum, they created a four-part payment plan with deadlines.


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