In this day and age, when vacations are few and far between, planning a vacation with the entire family can be both be economical and a lot of fun.  Once the hard part is over (the vacation is planned), you can sit back and soak it in because the memories made will deepen the bond between generations. Why is this important? In the busy world we live in, it’s easy to forget, “our lives, both start and end with family.” And this is certainly something to celebrate – but that doesn’t mean that planning a trip for a dozen people with different agendas and ages’ ranging from 6 to 76 is an easy task (something I recently did).



Multi-generation travel is growing in popularity as families are now spread across countries. Getting everyone together can be made easy when you meet in a neutral zone – a vacation destination. By booking a vacation rental you can easily find a home that comfortably sleeps everyone and boasts communal spaces – decks, patios, living rooms, spacious kitchens and private bathrooms and sleeping rooms that everyone craves.  Below are three strategies to keeping the entire family happy on your next multi-generation trip from toddler to elders.


Pictured on the left: this is the youngest on our trip trying out synthetic skating. It was ideal after a long walk to the park because there were food trucks and picnic benches for my grandmother to watch the kids while resting their feet!


Plan ahead – but don’t plan too much


While the planning stage can be overwhelming, it’s important that you take the time to ask questions – who wants to go, what’s the destination that would work for everyone (while limiting layovers) and what are people looking for…the beach, mountains, city, or even history? A fun way to get everyone involved in the planning practice is to create a Pinterest account where everyone can pin his or her favorite images and ideas of the ultimate vacation.



For those less tech savvy or too little to participate in Pinterest, they could cut out of magazines to create a vision board of their dream vacation. From there you can start to craft something that will meet in the middle and please everyone. I always find the pre- vacation work helps to amplify the excitement of the actual vacation!


Don’t plan too much. Once you have the destination and the long list of what everyone hopes to accomplish, be realistic with what you can get done in a day and be mindful of what people can physically do. For example – a 12-hour day at Disney might be ideal for some but is too much for little ones and great grandparents.


It’s also important to leave a piece of the day un-planned so that everyone in the group can choose to relax or keep going. This is a sure-fire way to keep everyone refreshed, happy and satisfied with the vacation. For example, the boys in our group wanted to try a wild boar hunt. So while they went hunting, the ladies in the family visited a spa.


Mindful of Money


Planning a multi-generation trip can be economical as there are opportunities to share costs and even get group discounts. Before booking your destination and accommodations set a budget that is within everyone’s means.


Have conversations ahead of time about how many meals you will go out for versus eating in and share the tasks of grocery shopping and cooking so that everyone has the opportunity to both participate and save.


Many vacation rental owners offer services that will have the groceries stocked at the home before you arrive to take away the stress of shopping for a large group. If you want to make dinner interesting, my family is a fan of playing “Chopped” where another person chooses ingredients and the Chef is surprised but has to make a meal in about an hour with what they are presented.



Celebrate Togetherness

Planning a vacation with multiple generations in tow can feel more stressful then a bad day for an air traffic controller. Remember – it’s about bringing everyone together and enjoying the uninterrupted time.


So don’t stress the small hiccups of travel, be sure to power down electronics when everyone’s together and celebrate the down time. With my family our best times on vacation is when we have nothing planned and aren’t spending money. We are simply hanging around the kitchen or living room sharing stories, laughing and eating…which is what makes renting a vacation rental perfect for gatherings.


Let’s be honest, how often do you get everyone under one roof? Get planning and get ready to enjoy every minute of it!