How to Create the Perfect Itinerary for a Family Trip

This is the 6th post in a Step-by-Step Guide to Planning Perfect Family Trip. Click here to start back at Step 1.

If you’ve been with me since step 1, you’re probably getting a little antsy to finally put everything together.

Well, you’re in luck, because the time has come!

So grab your research notes and your budget sheet. Pull up your custom map. Put the kids to bed and pour a glass of wine, because it’s about to get serious.

Let’s do this!

Now, a little disclaimer before we get started: There is no easy or perfect way of putting together an itinerary. Sure, you might get the perfect itinerary in the end, but it will take some trial and error. And if you have to redo things 3 times to get it right, that’s totally normal!

The real question is, how do you start filling things in? How do you decide what goes where, so you can create the best itinerary for your trip?

You want to be strategic in how you plan each day, so here are a few general rules I like to follow when planning an itinerary for a family trip:

1. Break your itinerary up by morning, afternoon, and evening.

If you’re using our free printable itineraries, you’ll notice I’ve done this for you already. This is for a very specific reason: I typically only plan 1 (maybe 2, if they’re short) must-see activities per time frame. I’ll then add in a “maybe” activity to fill in extra time if needed (knowing that if we don’t get to see it, we’ll be ok missing it). This creates an itinerary where you’re not too busy trying to see all of a city in a day, but you’ll never get bored either if something goes quicker than you thought it might.

2. Keep nearby activities and eateries together on the same days.

This seems like a big duh, but if you try to plan your activities by focusing each day in a different area of town, it will save you a lot of time and stress in the long run. If conquering a big city, label your days on the itinerary by what neighborhood you want to explore that day, and work to keep everything from that area together. That way there’s no rushing around town, you always know you have lunch or dinner plans nearby if the kids get hungry, you’ll save on transportation costs, and your schedule will have a lot more general flexibility. It’s an all-around win-win.

3. Start by filling in places you must visit at a specific day or time.

If there’s anything you need (or want) to visit on a specific day (i.e. Sunday morning brunch, Saturday farmer’s market, Monday free museum admission), add this to your itinerary first. This also includes penciling in your regularly scheduled nap time (more on that later).

4. Plan to visit some of the more well-known and busier sites on weekdays.

Particularly first thing in the morning if possible. You’ll be more likely to have the whole place to yourself or, at the very least, avoid mega-long lines. Fill in your weekends with more obscure, off-the-beaten-path type stuff that’s less likely to be busy.

5. If doing any tours, schedule those for your first day.

This will help you get acquainted with the city early on, giving you a lay of the land before you head out on your own. You’ll also have the chance to ask our tour guide for their own recommendations. There’s a good chance you’ll discover some new things you hadn’t built into your itinerary, and there’s nothing worse than taking a city tour on the last day of trip, only to realize you have no more time left to explore anything further.

6. Block off meals and downtime.

I’m always sure to make reservations for dinner (and lunch if I can) well in advance. We are foodies, so being able to get right in to the best restaurants in town (and note, by best, I don’t mean fanciest) saves us a lot of time, frustration and stress about where we’ll eat. Lunch and dinner plans are usually early (11/11:30 and 5/5:30). Not only is it easier to get reservations at these times, but it ensures that our cranky toddler has food on her plate before she even realizes she’s hungry.

And don’t forget to block off times to stop for a snack, play at the park, or (most importantly) return back to your base for a nap. For us that means planning to be back at our Airbnb from 1-3 PM, with very rare exception. We’ve also done nap times in the car, if you’ll have a rental, which can be a great way to let little ones get a nap in without having to return to your base (just be prepared to spend an hour or two relaxing in the car yourself!)

7. Leave your last day open.

Depending on how much time you have, you may not be able to leave it completely open, but if anything, plan a few “maybe” activities for all or part of your last day. It’s almost inevitable that you’ll discover something new throughout your trip that you didn’t find when planning. Or you may want to return to something you really loved. Having an open last day will allow you to finish your trip in a satisfying way.

8. Don’t forget to factor in travel time.

If you’re going to a big city where things are pretty far spread out (i.e. NYC), adding travel time into your itinerary is a must. This is where Google Maps will come in handy again, as you can find estimated travel times for walking or taking public transit between sites. Don’t be skimpy with this either. You can never underestimate how long it can take to get somewhere when you’re pushing a child around town.

9. Play around with the schedule.

It can be challenging to balance everything until it feels just right. You might get everything together and realize “crap, this restaurant is closed on Tuesdays” or “this museum isn’t open in the afternoon”. Maybe you’ll realize you’ve got too much stuff crammed in, and you need to start taking things out so you won’t feel stressed. Fine tuning is all a part of the process, so don’t be afraid to move things around or take things out until you get to the perfect itinerary.

So how does it look? My hope is that you’re feeling pretty confident in your planning and excited right now! You’ve done a lot of work, so you should give yourself a pat on the back.

Next, we’ll get back to reality and that dreaded “b” word. For now, bask in the glory of your perfect itinerary!