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My mom, or Memere as she is known to everyone else, is 84 years old and has been living with us for over 25 years. It is a journey not everyone would choose, but it has worked well for our family. God bless my hubby who has lived with five women (we have three daughters); he gets the superstar award. He is also prone to taking long, solo walks when we are on vacation.

It has been challenging to make vacations work for everyone. Thankfully, Memere is game for almost anything. When the girls were young, vacationing was fairly easy. Disney, camping, and beach vacations were staples. As they grew into teenagers and Memere got older, the challenges of getting everyone together, going somewhere we all thought was fun, and staying within budget became more complicated. Family vacations were just that, family friendly for everyone: Memere, the girls, sometimes extended family, and hubby and me.

Multigenerational trip to the beach.
Jim Quinn

Teenie Boppers And A Memere

The first time I remember the girls balking at a family vacation was a trip to Cape Cod, only a two-hour drive from our home. The girls were 13, 11, and 10; Memere was in her 70s. We rented a three-bedroom house near the beach for three nights. Simple, right? Not so much.

Tip: Let Them Bring A Friend

We decided each girl could invite a friend, meaning we put up six giggling, teenage and tweenage girls in two bedrooms. The two younger girls had to share with Memere. It was loud -- I longed for earplugs. It was logistically challenging -- we drove two cars everywhere. It was crazy -- everyone had a blast. Taking a half-dozen children on vacation sounds crazy, but our criteria was that the vacation be fun for everyone, and having all those girls certainly made the vacation memorable.

Tip: Don’t Insist They Hang Out With You 24/7

At the beach we let the girls stake out their own spot of sand, close enough so we could monitor, but far enough so they could feel like they were adulting. Result: happy girls who tried on a little independence, bonded with their friends, and buried each other in the sand!

Group photo in London.
Emily Barrett

Ditch Tradition: Do Something Different

Family vacations become harder to organize as children get into high school. All three girls played sports, so traditional April and February vacation weeks were dedicated team time. There was always a mandatory camp, game, or practice that made planning a school vacation-week trip impossible.

Tip: Get Creative With Your Vacation Weeks

For over 50 years (and several generations), we have hosted a Christmas Eve open house. It was a long-observed, mandatory family event! One year we broke with tradition and ditched all the Christmas festivities. We sent a minor shock wave through the family and rented a condo at Loon Mountain, New Hampshire. Instead of a big open house party, we had a quiet dinner in the condo and watched Christmas movies. Christmas morning we had stockings for everyone then hit the slopes. It was one of the best family vacations ever.

Tip: Divide And Conquer

At Loon Mountain, we were across the street from the ski hill. Hubby and the girls skied every day for a week. Memere and I, both non-skiers, swam in the pool, met them for lunch at the mountain, and enjoyed quiet reading time. After dinner, we would light a fire and all hunker down to play board games or watch family-friendly movies.

Join Forces: Vacation With Friends

The year before our oldest daughter was heading off to college, we vacationed at the Outer Banks in North Carolina. When the girls were younger, we would go to the Outer Banks every year. They were less than thrilled to be heading back -- particularly since it meant enduring the drive from Boston to Kittyhawk.

Tip: Plan A Vacation With Another Family

We teamed up with friends who had girls the same age to make this vacation happen. We each rented a condo unit in the same complex. The six girls hung out in one condo, the five adults (everyone loves having Memere along) in the other. This arrangement worked well. The girls stayed with their respective families at night but had a good amount of freedom during the day. At this point, they were 18, 16, and 15.

Tip: Drive To Your Vacation If You Have A Teen Driver

Driving to our destination ensured a car was available for our teens. I know you are saying “Yikes! Is she crazy?” I agree, this was a tough one. As confident as I was in my oldest daughter driving the two miles to take five girls out for ice cream, I held my breath for the hour they were gone. Bringing teenagers on vacation requires some parental creativity and, yes, lots of stress!

Having fun at Windsor Castle.
Olivia Barrett

One Big Happy (Royal) Family

When our middle daughter turned 19, she enrolled in a semester abroad in London. Lucky for us, my sister was living in London at the time. We couldn’t pass on the opportunity to visit London. Memere, of course, was totally on board to visit her daughter and granddaughter, too.

Tip: Enlist The Help Of Family Members

We were fortunate we could stay with my sister. My brother and his family also joined in. We planned two full-on family dinners and divided into interest groups, which changed daily. Having other family members along gives everyone options. Memere got to spend time with my sister, brother, and their families, giving us a little break.

Tip: Split The Group Differently Each Day

Our groups shifted daily. One day the girls went shopping and the boys toured to the War Museum; late in the afternoon we came together to ride the London Eye. Sometimes there were many groups of two or three, sometimes we split as family units, and we also took a few joint adventures. Changing how the groups are divided enlivens the conversation when you come back together.

Of course, it’s not always perfect. A photo of our middle daughter practicing her martial arts moves on her older sister at Windsor Castle captures a classic “I give up” moment. I’m in the gray sweater ignoring them!

Challenges Are Opportunities

Multigenerational travel is challenging, but with careful planning, it is also rewarding.

What’s up next for this galavanting group? Memere wants an Alaskan cruise. We will be a dozen family members and their significant others, plus a few grandbabies. Look out Anchorage, here we come!

Planning a multigenerational or multi-family vacation? Here are some common group travel getaways and how to overcome them.

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