Tips for planning a family reunion or group trip itinerary

Family reunions and group trips can be such a rewarding experience, but the planning process?  Not so much.  

But here at the Brown County Barn Burner, we are the unofficial Midwest experts trip planning for large groups and family reunion trips. So I’ve compiled all my tried and true tips for creating your own family reunion trip itinerary to help make planning your next big getaway a breeze!  I’ll also share some examples of how these tips apply specifically to visits to Brown County, Indiana - feel free to steal these for your next trip to Nashville, or just use them to guide your own planning in general, no matter where you’re traveling.

(NOTE: If you’re reading this post, I assume you already have a location picked (hopefully Brown County or Nashville, Indiana?) and that you are ready to start planning your specific itinerary, so that’s what these tips will focus on.  If you’re just in the beginning stages of considering a family reunion or group trip, and still need help picking a location, then start with this post.)

So with that in mind. Let’s talk more about my guiding principles I use when planning, especially for a larger group and when kids are involved (these guidelines work for any trip, but I do find that all adult groups have a little more leeway in how and what they plan for their itinerary):

keep the itinerary loose and the activities flexible

As you dive into planning, remember - for a family reunion or large group trip, spending time together is likely your main priority.  You aren’t trying to check off every major attraction in a new city, with every day full of non-stop activities.  Obviously you and your group will still want some things to do, but we’re going to keep the overall pace slower.  This approach for a group trip will help everyone keep their sanity, make the entire experience more relaxing, and give everyone time to reconnect and catch-up with each other.

I am definitely the planner in my family, but I’ve learned that trying to keep too rigid a schedule on any trip will just pile extra stress on you as the schedule keeper and take away a lot of the potential for fun and spontaneity.  Having a loose idea of the activities you want to do, while keeping your itinerary as flexible as possible, is especially important for larger group or family trips, especially when kids are involved.  In order to accomplish this, I recommend that you:

  • Pick 2-4 things MAXIMUM (depending on the length of your trip) that you consider “Must Dos” and prioritize those.  There will likely be more things you’d LIKE to do - if time, weather, and the grace of the universe allows - but identify your absolute priorities in advance.

  • I like to plan and group activity ideas in 3 to 4-ish hour chunks of time, and just have those ideas ready to plug into any given day, depending on what sounds good to the group.  However, if any of your “Must Dos” require booking or buying tickets in advance, then go ahead and do that and know that the rest of your schedule will have to work around that timing.

  • With a large group, try and limit yourself to 1-2 on-the-go activities PER DAY.  No more.  And going out to eat at an actual restaurant counts as an ‘activity.’  Trust me - your future self will thank you for this decision.  And, if for some reason you must pack one day full, then try and leave the following day more open-ended and relaxing.  

  • Be sure to check the local Visitor’s Center or other local websites for an up-to-date Events Calendar, in case there are special festivals or other events occurring during the dates you’ll be visiting.  A simple Google search should bring this up for any place you’re visiting, but in Brown County the sites to check are:

Your lodging host can also be a great resource for activity recommendations.  For our guests at the Barn Burner, we maintain a “Things To Do” page, a Google Map with different location pins, other posts with specialty event ideas like our Shopping Guide, and I’m always happy to provide specific recommendations when guests ask.

make a food plan in advance (it will safe you money And your sanity)

It’s a fact of the universe that we all have to eat and, as a mom and someone that generally enjoys cooking, I spend A LOT of my own mental energy and time planning out what my family is going to eat next.  But figuring out food and meals for a large group on a trip requires a whole different level of planning!  But it does not have to be stressful or break the bank if you take a few things into account in advance:

Limit the number of times you’ll go out to eat as a group

Unfortunately, going out to eat as a large group, or with a bunch of little kids, is really not that fun.  Once or twice during the trip?  That’s fine (and can be perfectly enjoyable if you pick a restaurant that’s a good fit for the group) but any more than that and it’s going to be $$$ expensive and probably give you a headache...

If you’re traveling with a group of more than 8 people, I suggest limiting meals out to once every other day, AT THE MOST, and preferably pick restaurants that take reservations.  Splitting up into smaller groups to go out to eat more often is fine.  Getting carryout is also fine.  But sitting in a restaurant as a group of 10+ people on a regular basis will wear on anyone’s nerves and level of enjoyment.

Ordering carryout can be a way to experience different restaurants without the hassle of eating there in person.  But keep in mind that coordinating a carryout order for a large group can be a real headache, so it’s probably easier to stick with something more straightforward like pizza.

pick a lodging option with a fully stocked kitchen (and dishwasher)

This will allow you to more easily eat some meals in, instead of always going out.  Split up and assign specific meals (and clean-up duties) in advance, to minimize the amount of planning and packing for everyone.  Depending on the group size and trip length, you may want to use a service like Sign-up Genius or Google Forms to streamline this.

Consider bringing some prepared foods with you

This doesn’t need to be anything extravagant, but just having some pre-made lasagna, or soup and salad ready to go, can easily check off a meal for the group without requiring a lot of prep on-site.  For larger groups, you could also consider hiring a local private chef or catering company to handle some of your meals for you.  It can be more affordable than you’d think and your lodging host should be able to suggest some good options. Here’s a list of private chefs, caterers, and restaurants we’d recommend in Brown County.

Agree that not every activity needs to be something that the whole group does together

It’s not just restaurant outings that can be better enjoyed with a smaller group.  There are certain activities that are best done with a smaller group, or that some people won’t have any interest in at all, and that’s OK!  If you can find a way to balance time together with more individualized activities, I promise everyone will have more fun.  

I’m a big fan of splitting up for different activities occasionally on any trip (in fact my husband and I will even do this sometimes when it’s just the two of us on a trip).  But I find that the larger the group, the more likely this mindset is to be beneficial, especially if there’s a wide variety of ages in the mix.  This is also why I always encourage finding lodging where you can all stay together, in the same space.  When you know that you’re all coming back together at the end of the day (rather than staying in different places or hotel rooms) you know that you’ll still have time with each other, and there’s less pressure to stay with the group every minute throughout the day.

try and find lodging that will allow you to walk to some activities

Staying within walking distance of some potential activities or dining options is a major bonus and makes it a lot easier to improvise.  And the walkability options from your lodging don’t need to be extensive, although the more options you have the better, in my opinion.  

Staying in a walkable area will reduce the hassle of coordinating driving and parking, as well as giving your whole group more flexibility with their itinerary.  Even if it’s just a nearby hiking or multi-use trail, a playground, or a neighborhood coffee or ice cream shop - any amount of walkability will make it easier to take advantage of impromptu outings.

Have some back-up ideas and activities, just in case

No matter what you do, sometimes things just won’t go as planned.  Sometimes the weather isn’t cooperating, someone isn’t feeling well, or an attraction is closed unexpectedly, so it’s always a good idea to have some easy back-up/filler activities with you, just in case.  

Ideally your lodging will supply some options - we provide a few easy games, puzzles, and building blocks in all of our units at the Brown County Barn Burner - but you can also pack some options of your own.  This doesn’t have to be anything crazy, and it definitely doesn’t need to take up a lot of room in your car.  Here are some options I recommend (Disclosure: Some of the links below are affiliate links. This means that, at zero cost to you, I will earn an affiliate commission if you click through the link and finalize a purchase.):

Basically, be ready to just hang out at your unit for an afternoon or slower morning if needed.  Microwave popcorn and s’mores supplies also go a long way towards making basic down time feel special.

Start planning your next group or family reunion trip now!

Hopefully these tips should make planning your next large group or family reunion trip a little easier, no matter where you choose to go!  But if you’re looking for a family reunion location in the Midwest, and want to make things even simpler, then I definitely recommend putting the Brown County Barn Burner at the top of your list for lodging!  You can read more about our spaces here or contact us with any questions.

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How to Choose Activities for Your Next Group or Family Trip itinerary

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Best Family Reunion Locations in the Midwest