How to Plan Your First Multi-Generational Family Vacation

I guess you could say this was our big year for multigenerational travel. We didn’t really plan it that way, it just sort of happened. Maybe it’s that our parents are getting older and the desire is stronger than ever to spend quality time with them. Not just the typical time to celebrate holidays or help with carpool, but time set aside to experience something new and amazing together and make meaningful memories together. So when our family began talking about spending a month in Europe over the holidays, my husband’s parents soon became part of the conversation. When they expressed an interest in going, we were all delighted. Soon plans were underway for our big multi-generational family vacation.

Multi-Generational Family Vacation
Hallstatt, Austria Photo: Dianne Sivulka

When my friends heard that we would be spending a month in Europe with my in-laws, brows furrowed. But I had a feeling it would be great because our relationship is great. What I did not know then however, was that it would be a collection of memories that would rival one of the best travel experiences we have ever had. Sure, the museums, European pastries and castles were epic, but when I think back to the experience, the real standout is the time we spent together as parents, kids and grandparents and the memories we shared. Just four months later, we did something similar with my parents, only this time to French Polynesia for a two week vacation. Again, the memories that stand out most in my mind are not just the amazing experiences we had ourselves, but that we had them together. I will never forget snorkeling in the most beautiful coral garden I have ever seen, with my mom on one side and my son on the other. These have been cherished memories indeed.

So what are you waiting for? It’s time to plan a multi-generational family vacation of your own! But first, take a look at our five tips that will help you have the best time ever.

Multi-Generational Family Vacation
Grammy and the boys – heading to dinner at the Hilton Nui Bora Bora Photo: Dianne Sivulka

1.Have a realistic outlook

You know your family best and the unique dynamics you share. If family holidays are stressful because of strong personalities and common annoyances, then don’t suddenly get amnesia when thinking of going on a trip together. It’s important to realize that people don’t change just because they’re traveling. Your children will not behave differently on the road than they do at home. And neither will your parents. So if your dad gets annoyed when your toddler whines through dinner or you are not a fan of the way your mom is constantly tidying up, be prepared for these things to still exist while you’re in paradise together. Set the vacation for success from the earliest stages of planning. Is it a smart choice to share a suite together or would it be better to have your own space? Ignoring things or pretending behaviors don’t exist won’t help. That leads me to my next tip… communication.

Multi-Generational Family Vacation
Fun with Grandpa in Bora Bora Photo: Dianne Sivulka

2. Communicate and be flexible

It’s important that the lines of communication start open in the planning stages and remain open through the vacation. Include everyone in the decisions for itinerary, accommodations and planned activities. Be sure to discuss finances, like who will pay for what, and what will be shared. Expectations should also be clearly communicated by everyone involved. If you’re traveling with young children you might want to make the expectation clear that each afternoon you’ll be spending some down time in the hotel room for naps and rest. Or that you’d prefer not to have lengthy dinners out every night. When my mom began our trip to French Polynesia by handing each of our kids a box of candy just as we were about to board an 8 hour red-eye flight, we found ourselves face-to-face with a communication necessity. She meant well and of course, the kids had no gripes about her generosity. But it was important for my husband and me to lovingly communicate that all future candy dispensaries should first go through us (also known as the Candy Police). Sure, it may be uncomfortable, but it saves frustration down the road. When expectations like these don’t get communicated, then resentment can easily set in. Likewise, it’s important for everyone to work hard at being flexible. When we’re home we all have our routines. We like things a certain way. This is true for you, your kids and your parents. Flexibility goes a long way in travel and especially when you travel with others.

Multi-Generational Family Vacation
Moorea, French Polynesia Photo: Dianne Sivulka

3. Plan to spend some time apart

Everyone needs a break sometimes. If you feel like you have to do every single thing together, then you might get a little tired of each other and even feel trapped. Perhaps your parents would like to get away and have dinner by themselves. Remember, they raised their kids a while ago and spending 24/7 with little ones can be exhausting! Or maybe there is a special place you’d like to take your kids, but others in the group would rather head a different direction. It’s okay to spread out and then come back together at a different time. On one particular day in Salzburg, we all spent the morning together taking the Sound of Music tour, but when we got back everyone had a different idea of how to spend the afternoon. So we divided up and it worked out great. My husband went back to the hotel to get a little work done, my in-laws walked through town and did a little shopping, and I took the boys to a children’s museum. The nice thing about spending some time apart is that no one feels obligated to do what others want to do all of the time. And then you’re happy to come together again and share your experiences. Spending time apart could also mean date night for you and your spouse! Yes, please! Or it could mean a day where the girls head off in one direction and the guys in another.

Multi-Generational Family Vacation
Cesky Krumlov Castle, Czech Republic Photo: Dianne Sivulka

4. Be creative

This is a unique time and should be remembered in special ways. Consider working on a group journal together or giving special attention to a project. Collect something of a particular theme and get the whole family involved. If you’re going on a beach vacation, collect shells. If you’re going to the countryside, collect and press wild flowers. My 12-year-old son, along with Grandpa, really got into photographing foreign car logos while in Europe. Anytime they saw a new car logo they hadn’t photographed yet, they captured it. It became a fun scavenger hunt for them and a great common effort. A group journal could be a place where everyone writes or draws a special memory from that day. This might be a fun activity at dinner when waiting for the food to arrive. Bring along a high-quality art journal and some colored pencils. Also bring some double-sided tape to include memorabilia like ticket stubs or postcards. No doubt, this journal will be a treasure to keep long beyond the vacation.

5. Have fun and live in the moment

Appreciate the rare opportunity you have and treat each moment like it matters. Savor every sunset, every child giggle, and every conversation. Take a walk on the beach. Hold hands and cuddle. Play hide-and-go seek or a board game. Limit your time on electronic devices and be with the people you love. Before you know it, you’ll be home and back in your regular routine with only the memories of the vacation to hang on to. When I asked my son what he enjoyed most about traveling with grandparents this year he replied, “I liked traveling with a bigger group because there was always someone to do something with. And I liked sharing great memories with our favorite people.” I think that sums up the benefits of a multi-generational family vacation.

About Dianne Sivulka

Dianne Sivulka is a former teacher who became a stay-at-home mom and homeschooler. Today she and her husband are traveling near and far with their boys every chance they get. She writes about educational travel tips at ourEDventures. Follow her on Instagram and Pinterest.

Click here to read Dianne's articles

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