7 Tips to Make Your Next Multi-Family, Multi-Generational Trip Wildly Successful

It's not easy, but it is possible

August 22, 2023 6:07 am
How to keep 20+ people happy on vacation
How to keep 20+ people happy on vacation

For the last 20 summers, we have planned and enjoyed an amazing multi-family, multi-generational, week-long trip. At first, it was just us, my parents, my siblings and our spouses. But as our families grew, the guest list expanded to its current size — 21 people, ranging in ages from six to 80. Sometimes we rent a huge house by the lake and opt for low key beachy relaxation, but other years we pick a more ambitious (and spendy) destination — like this summer, for example, when we took our brood to the Azores. We all consider this week together the best week of the year, but our success hasn’t been without unintended face plants along the way. Here’s what I’ve learned, and what you’ll want to consider, when planning your next multi-generational trip. 

Pick the Right Trip for Your Family

A great trip starts with a great concept, but not all trips will be right for your crew. Before digging into dates and specific destinations, think about who’s coming on this trip. What’s going to make a great trip for them? What will their specific blood-pressure-lowering needs be? Does anyone have littles who will need to be in bed by 8 p.m. every night? (Think about a place where they can put the kids down and then come safely hang with the group.) Does anyone have mobility issues? (Biking through Tuscany is probably out.) Depending on the answers to these questions, you may opt for a certain type of trip and not another. Cruises are great vacations for groups with mobility issues and childcare needs, for instance, and house rentals are great for accommodating a range of bedtimes or picky eaters.

Know who’s paying and what everyone can afford
Know who’s paying and what everyone can afford

Know Who’s Paying and What Everyone Can Afford

This is important to understand up front. Are the grandparents paying for everyone? If so, what’s their budget? Is everyone paying for themselves? Float some cost ranges for the week, see how they sit with everyone and adjust as necessary. If the numbers are big, make sure you give everyone plenty of time to save up. If someone is having a tight year, scale down the plan and the cost to accommodate. The trip should be financially comfortable for everyone. 

Consider Hiring a Planner

If your trip is a VRBO by the lake, you likely won’t need a trip planner. But if your plan is a high-octane tour of European capitols, you’ll be much happier if you leave the planning to a knowledgeable third party. Yes, it is slightly more expensive than DIY planning, but the benefits far outweigh the extra cost. Your planner will handle all the icky things, like collecting payments from each family, booking flights, dealing with any cancellations and answering the 134,564 questions your crew will have before departure. 

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Lock in About 70% of Your Activities

Downtime is important in big groups, but so are outings. When you’re hanging with family and a thousand cousins, you run the risk of happy inertia — there will be a strong urge to just hang out with these fun people and never leave your hotel. But you want to see this amazing destination! Make sure you have at least one thing planned every day to get your group up and out. 

Come Up With a Dinner Strategy for the Week

In my experience, dinner is among the most hard-to-align-on moments of the entire week. Someone wants cheap, someone else wants to try the cool, trendy restaurant they read about around the corner. Someone else thought they would want to go out fancy tonight but is exhausted from the day and now just wants to get dinner off the hotel pool menu. 

If you’re all staying together at a VRBO, one way to handle meals is to assign each family a night or two where they’ll be responsible for planning and cooking for everyone. If you’re staying at a hotel or resort in a vacation destination, it can often be hard to eat out with a big group. Consider asking your planner to help you advance-book a big group welcome dinner when you arrive, and then a farewell dinner on the last night — then advise everyone to fend for themselves for other dinners during the trip. If families’ plans align on any given night — amazing! If not, no pressure.

Be easy like Sunday morning
Be easy like Sunday morning

Be Easy Like Sunday Morning

It may go without saying that traveling with 20+ people, even if (or especially if) they are related to you, can at times feel like chaos. Families with different aged kids or no kids, different parenting philosophies, different budgets and different interests can be a recipe for conflict. Make sure you approach this week with the most open of minds, figure out what your family’s must-dos are and be fluid with everything else.

Break Off on Your Own

Do not feel bad about breaking away from the group and doing your own thing. This is how to get your must-dos in. I have big kids who really wanted to surf in the Azores — one day, when we didn’t have a tour planned, we rented a car and found the surfing beach. My sister’s family joined, but the rest of the crew who have little kids did their own thing. My mom did a food tour, which was her must-do. On another day, some of the other families went scuba diving while we hiked. Getting the balance of group and small family activities right — and doing exactly what you and your family want to do on any given day — is key. 


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