How to Plan the Ultimate Family Getaway

Tips for a successful multi-generational vacation

The southwest shore of Maui, photo by Timothy Fowler

You can lose track of how many times you’ve been to Hawaii. I have. But, after vacationing on five of the islands, Maui remains my favourite, with the most memorable visit to that verdant island having been a whole-family affair. We would have done it sooner but for the tension between planners and improvisers. Some of us live by our calendar; some fly by the seat of our pants. There was that, and the fact we only had one set of in-laws, and we didn’t want to mess that up.

Our sons married sisters. We love the women they chose, and their parents. I figured, why not plan a Maui family vacation for the most important people in the world, a group composed of three generations, four families made up of two pairs of siblings, two sets of grandparents and grandkids?

We asked: “Wanna go to Maui on vacation?” “All of us?” came the response. Though there were planning pitfalls to avoid, the subsequent steps were surprisingly simple.

Photo by Yinyang/iStock

We called a family planning session and ordered pizza. Each family member was involved in the conversation. Even the little ones were given the opportunity to express their Maui-trip ambitions. We respected each other’s need for personal vacation space and time. We agreed not to do things en masse, unless we felt like it. We booked separate condos in a resort with multiple pools, an outdoor communal kitchen and tandem barbecues, and we rented cars for flexibility and independence.

Something special happened on that trip. We snorkelled, read, body surfed, walked, rested and ordered pupus (appetizers) at the barefoot bar, but we also connected in a way families dream of. Profoundly relaxed, we shed stress. Each of us worked hard to respect the vacation framework we had constructed, and it served us well. We recounted daily experiences at potluck suppers while the main dish sizzled on the barbecue and the kids splashed in the pool. Tired young parents got two nights on their own as grandparents hosted the little ones. I got one-on-one time with each of my kids and their wives, and rocked my granddaughter to sleep after we shared a day in the Maui sun. My oldest son and I rolled the throttle on big V-twin motorcycles as we wound around the North Loop Coastline Highway 30 from Kapalua to Paia and up a stretch of Highway 377 toward Haleakala. It seemed we never lost sight of the ocean.

Friends tell me my Maui family holiday experience is remarkable, but our family-travel secret is simple: Plan activities every other day, and let the in-between ones just happen. Step one is asking “Wanna go on vacation?”

Getting there: WestJet flies to Maui 20 times a week from Vancouver, Calgary and Edmonton.

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