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How To Plan A Multi-Generational Family Vacation

You’ve heard it at every family gathering, “we should plan a family trip” ...and that’s about as far as that plan goes. Understandably, planning a family trip for you and your extended family feels like a near impossible task but it's also the most memorable and best family-bonding experience a family can have! As experts in hosting hundreds of family reunions and annual trips, we’ve compiled a list of tips and tricks to make your multi-generational family trip not only doable but enjoyable!

By Payton Soriano on 9/1/2026
Family Vacation group stays

Pick Your Dates Far in Advance

…and stick to it! There will always be kids’ sports, work limitations, and endless excuses that get in the way. Planning far in advance gives everyone time to prepare their schedules to accommodate the trip. Do your best to pick dates that will work for everyone but know that it's very rare to have a weekend that works for everyone. 

How To Pick a Date

Everyone’s schedules are different but the one thing every family has in common is birthdays and anniversaries. Whether it’s your uncle’s 50th birthday or grandma & grandpa’s wedding anniversary, it’s always easier for the family to opt-in when there’s a common goal or reason for celebration. 

Choose Your Destination

When booking a trip, most people choose a place to stay and then choose a place to play. At Big Sky Barnhouse, we’ve taken this multi-step planning process out and created Airbnbs that are designed for both stay & play. With pools, hot tubs, mini golf courses, playgrounds, basketball courts, golf simulators, ping pong tables, speakeasies, karaoke stages, arcade games, and acres of peace and quiet, there truly is something for everyone at all of our Big Sky Barnhouses. 

Traveling With Infants and Elders

A hidden feature that all of our Airbnb barns feature is the comfort for both the youngest and oldest members of your family. For many of our aging grandparents, a family trip might feel impractical and even impossible. By including all the amenities and activities in the same place as your family is staying, there is always a comfy chair for grandpa to sit and feel included. There’s also always a clean, private bathroom to change babies’ diapers or put them down for a nap without having to leave the function! 

Meal Planning

Thank goodness for Costco and Sam’s Club! Our best suggestion for extended-family vacations is a good grocery haul. There’s no need to overcomplicate either! Here’s our suggestions for meal planning. For breakfast, fresh fruit, complete pancake mix and plenty of eggs go a long way. (We keep the coffee stocked! Just bring your favorite creamer.) You can never go wrong with a good PB&J lunch (except if you’re allergic to nuts). Keep dinner easy too with a pasta night, burgers and hot dogs on the grill, tacos, or your favorite family recipe. A crockpot will be your best friend to keep food warm all night for seconds!

Rotate which individual family cooks meals so everyone gets a turn to relax. 

Pro Tip: Task the kids of the family to cook dinner on their own! Not only will you be entertained but also have stories to tell for ages. It’s always good to know which kid doesn’t know how to boil water. 

Budgeting

Factoring in affordability is a key component to your whole family’s attendance in a family trip. When renting an Airbnb, the cost-per-person decreases as more people attend. This not only helps financially but also helps everyone have the common goal of having as many people join the trip as possible. Also, renting one large shared house (or barn) is simply superior to each family having an individual hotel room and doing the weird shuffle across the public hall to all hangout in one room that’s much too small for 30 people anyhow. 

Pass The Vibe Check

The easiest way to get a quick “yes” from the whole family is finding a place that passes “the vibe check” from everyone. This is no easy feat! We’ve specifically engineered our barns to have the “wow factor” for teens, tikes, parents, and grandparents. With playgrounds, mini golf, and sports courts, everyone’s inner child feels at-home here. Vibrant murals, the most creative assortment of activities at your disposal, and no set agenda is the perfect set-up for hours of play and laughter. 

Pull up our social media or any barn page during your next family gathering and even your grumpiest teenager or uncle will have to admit they’d have fun here!

Most Importantly: Have Fun! 

Life is short. Make it fun. If you’re lucky enough to have a family you’re thinking about taking a vacation with, do it! Memories you make on vacation are ones you get to cherish forever. The greatest gift you can give your family is time well-spent together. Our mission at Big Sky Barnhouse is to provide the backdrop for those memories. 

So, what are you waiting for? Start your group chat and get to planning your next adventure!