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  • Maestro Associates

How to Plan for a Multi-Generational Family Vacation

With about 40% of leisure travel falling into the multi-generational category, it’s clear that extended family vacations are here to stay. The abundance of baby boomers retiring and wanting to spend more time with their children and grandchildren paired with the experiential travel goals of Gen Zers means extended families are, more and more, choosing to spend their vacation days together. And, with so many grandparents being forced to take a hiatus from hanging out with loved ones due to COVID restrictions, many families are making time with extended family a top priority in 2021!


If you’re one of the many that’s itching to hit the road or skies again once it’s safe to do so, consider these six tips for how to make your next family trip one for the books.


☑︎ Make sure everyone feels as though they are part of the decision-making process. Get an email or text chain going, schedule a conference call, or hop on a Zoom. With open communication and a little compromise, you can make sure you’re kicking off your trip on the right foot.


☑︎ Talk money early and often. Have a frank conversation with everyone involved about overall budgets. The last thing you want is to be locked into a vacation leaving you cash strapped and unable to enjoy activities and outings.


☑︎ Designate a captain. Be sure to include everyone when brainstorming locations, types of housing, desired activities -- but once the major themes are decided, hand the ball to a designated ‘captain’.


☑︎ Acknowledge that activities are optional. Plan ahead a couple of group activities before arriving at your destination, but then recognize that it’s okay to not do everything together. Be upfront about expectations when it comes to day-to-day activities -- it’s okay to want some alone or immediate family time even on a group trip.


☑︎ Remember to schedule downtime. New places mean new experiences, new restaurants, and a never-ending list of things to do! But without fail, every generation needs downtime, so treat it like any other activity and schedule it to make sure it’s not overlooked resulting in tired, cranky kids (parents, grandparents, aunts, uncles, etc.)


☑︎ Grandparents aren’t coming along just to be babysitters. The connection that can be built during a vacation where everyone is huddled up together in a shared home is undeniable. But remember that just because grandparents may be willing to babysit, it’s their vacation too. They will want some alone time too, especially after long days of keeping up with youngsters.

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