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

As I covered in detail in this post, planning a successful itinerary for a group or family trip is part art and part science, but there are some tried-and-true steps that will help you plan a trip that’s more enjoyable for everyone involved (including you).  Again, this post goes into a lot more detail about these points, with links and examples, but to summarize:

  • Keep the itinerary loose and the activities flexible.  

  • Do most of your food planning in advance and limit the amount of times you’ll eat out.

  • Agree that not every activity needs to be something that the entire group does together.  

  • Try and find lodging that will allow you to walk to some activities.  It’s a major bonus and makes it easier to improvise.

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

Now you may read those guidelines and think it all sounds well and good, but are also wondering HOW to actually incorporate them into your trip planning efforts?  So let’s go one step further and look at how to gather ideas and choose the activities for your next group or family trip.

what mix of activities makes the perfect Itinerary?

In my opinion, the perfect day (no matter where you’re at) contains elements of each of these three things - Movement; Entertainment/Amazement; and Nourishment.  How exactly you incorporate each of these will vary from group to group, based on a variety of factors.  But ideally you want to find balance along the spectrum from super simple and basic to complicated and strenuous between these different categories as you’re piecing together your days and itinerary for any trip.  This will help ensure you don’t end your trip totally exhausted or miss out on the opportunity to experience the area you’re visiting.  

Here’s some more context of what I mean by each of these categories to help you start brainstorming for your next trip:  

  • MOVEMENT - This can mean physically moving and exerting your body (whether that’s a strenuous workout or simply walking around to explore) OR it can mean motorized travel as part of getting to your destination or going on some sort of tour or excursion.  Travel-heavy days can be really exhausting, even if you’re just sitting the entire time, so you want to take that into account with your planning.

  • ENTERTAINMENT/AMAZEMENT - This can mean literally seeing a show or performance of some type, taking time to soak up the sights and wonders of wherever you’re traveling, or just doing something you really enjoy but might not normally make time for, like playing board games, reading a good book, going shopping, or going out to eat a great meal (bonus if there’s live music!).

  • NOURISHMENT - This can come in the form of food and physically nourishing your body, activities that provide necessary rest (slow mornings, nights around the fire, etc), or making time to build relationships and strengthen connections with the group you’re traveling with.

As you research your destination and brainstorm ideas for your itinerary, you’ll find that certain activities can actually check the box for more than one of these categories.  Once you have some options listed out, you’ll mix and match between categories to build out options for a full day.  Whenever possible, I prefer to do the brainstorming part in advance, but then I wait to pick what will happen on each day until closer to time (even just a day or two prior) so that I can make plans based on the weather forecast, the group’s general mood, etc.

How to gather trip itinerary ideas

So, how do you find the options to fill out your list of possibilities in advance?  The internet is definitely your friend here. To start, you can simply Google “things to do in CITY NAME” for ideas. Or, most cities and counties (even if they’re small) will have a Visitor’s Bureau that you can contact for ideas.  For example, in our area the Brown County Convention and Visitors Bureau website is extensive and has lots of ideas for your trip and guides you can download to help with planning.

If you already have lodging booked, the owner or host should also be a good resource for what’s in the area, and can probably provide some options that are less well-known and might be a good fit for your group’s interests.  We keep a general list of “Things to Do” on our website, but I’m always happy to provide more specific recommendations when guests ask. 

Ultimately, this list is likely going to look very different for every person that’s planning.  We all have different interests, desires, and ability levels.  And even if there’s a lot of overlap, a trip to Brown County with kids is going to look different than a trip to Brown County with a group of your girlfriends.  I like hiking and vintage shopping, while you might prefer boutiques and wine tasting.  There’s no “right” or “wrong” here - as you’re listing out ideas, it’s about what YOU and YOUR GROUP want to do.

How to organize trip itinerary ideas

Basically, you’re going to start your research and begin listing ideas.  As you’re going through, make sure to take note of if there are certain hours or days closed that you need to keep in mind.  Also, depending on the geography of where you’re going, you may want to note certain things that are in the same general vicinity so that you can create efficient combinations. This can be done in any notebook, and I’m also working on a free printable that you could use instead.

I also use the “Save” feature on Google Maps extensively for this planning process - I put a “Heart” on the location of my lodging, so that it really stands out, I have a separate list for restaurants I’m interested in, and everything else gets a green “Want to go” save.  You could differentiate further, but I find this works well enough for marking shops and points of interest that I want to remember.  And it makes it easier to see the bigger picture of what is where as I think about which activities to group.

pulling everything together and what’s next?

As you’re doing your research, start off by just compiling a list of ideas that catch your interest and based on what you know your group enjoys - you’ll mix, match, and pick specific activities later. You want each day to include at least one aspect from each category of “Movement, “Entertainment,” and “Nourishment,” but the specific options you list out are going to be heavily influenced by the destination that you’re traveling to and the lodging you’ve chosen. 

If where you’re staying doesn’t have a full kitchen, then “make dinner in” isn’t really going to be a viable food option.  It’s more difficult to have “play board games” as an option if you’re staying in a hotel.  And, at the same time, if you’re staying at a cabin in the woods, “walk to get ice cream in the afternoon” probably isn’t an option either.

Stay tuned for my next post where I’ll share example activities for a Brown County or Nashville, Indiana trip to give you an idea of things to consider for your next trip, no matter where you’re traveling. Or, if you want to make it even simpler for yourself, start planning your stay at the Brown County Barn Burner and let me help you pull together something amazing!

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Tips for planning a family reunion or group trip itinerary