The planning step is often the hardest part.  Yes, plenty of people just fly by the seat of their pants, and make it just fine.  But taking the time to make an itinerary will make the trip so much more relaxing and fun.  That’s especially true for those with kids in tow and/or limited time (and, let’s face it, time is ALWAYS a problem).  

After all of your Pinterest inspiration, and map-based plotting, it’s time to make a list. Start by dividing your options into two groups:

1. Must do: this is, obviously, the list of things that you absolutely can’t miss on this trip.
2. Hope to do: this one usually gets pretty long (but it’s supposed to!)

When I’m out and about, I jot down ideas in the notes on my phone, then add them to my list later.

Before you even start on your itinerary, look at your “must-do” list and make sure that you plan around any events or festivals that may be happening.  Imagine planning the perfect trip to Paris, only to discover that the Tour de France is coming through that day. If you want to see it that’s great, but maybe you want to see the the city without roadblocks and crowds all over the city.  Major events will also limit hotel and apartment options, and drive up the price. So, it’s just better to know early on so you can plan accordingly.

The same is true for hours of operation.  Back to the Paris example, did you know that the Louvre is closed on Tuesday??  If it’s a must-see, and you plan to be in Paris on Tuesday only, you’ll be SO disappointed!

Get on your computer and find an online calendar to work with, or print one out.  (I always print one, but usually go through three or four before I get it right.)  My go-to is Google Calendar, mostly because it’s part of a fantastic suite of products that are great for planning.

By this point, you probably have your flights booked, or at least know your time frame, so put that on the calendar and work from the outside in.  If, say, you fly in to Paris, then out of Rome two weeks later, you at least already have a couple of places set.  Then hit Google Maps, start checking travel times and work your way back to the middle.  

I almost always do open-jaw tickets (in to one city and out of another), when the location is conducive to ground transportation or cheap local airlines (and that’s most places these days).  You get to see more because you aren’t spending time backtracking, and the additional cost is usually minimal.

Making the calendar is by far the longest and hardest part of the process, mostly because it involves deciding where to cut.

My secret to getting over FOMO (fear of missing out) is to believe that you will make it to those missed places on another trip.  When we tell people about trips we are taking, I so often hear “Oh, what a trip of a lifetime”.  If you look at it like a once-in-a-lifetime experience, then of course you will want to see EVERYTHING.

Deciding to cut Montenegro (just one little hour further) from our last trip was SO hard!  I held on to the idea for the longest time, but realistically we would have been miserable.  Yes, we could have seen it, but everyone would have been cranky, it would have been super-quick, and we would have missed out on other things in Dubrovnik.  

Once you’ve checked all your travel times and hours of operation, it’s time to make your final calendar and start booking.  These are our go to sites for the best deals.

I’ve tried all of the apps, hoping for a fantastic digital solution, but just haven’t loved anything like my trusty Word or Google Doc.  Plus, a document is printable, which is essential for all of those times you find yourself in a foreign country, not speaking the language, and without internet until you get to your apartment.  What’s that address again??  What’s the code for the keypad??  It’s all on the printout!

Start with the obvious stuff: the flight information and any accommodation contact numbers and instructions.  Then make sure you write down what’s been paid ahead and what will have to be paid on site, often in the local currency. Also, this keeps you from being double charged; a printed receipt is so useful if an apartment manager is trying to collect money when you know you already paid.  

I’ve had to make several last-minute runs to the ATM to grab more currency because I forgot that it was to be paid on site, and not charged to my card. 

Finally, I add a list of activities and places to eat for each day.  None of these are set in stone, but it helps when you know that a certain activity is only available on certain dates or at certain times.  Also, how many times have I gotten up and asked my gang, “What do you want to do today?”, to be met with, “I don’t know”?   (Yep, for me, almost every day.)  This way you have options to present everyone and can choose what you feel like doing that day.

Same goes with food.  I never used to keep a list of restaurants to try, so at mealtimes we would inevitably end up wandering around for what seemed like forever, hoping to stumble upon a quaint local haunt with phenomenal food.  That’s not super-likely, so now I keep a list of places with quick descriptions (like café next to playground, or higher-end but kid-friendly) so I know what to expect based on the kids’ (and our) moods and energy levels after a day of sightseeing.  I also note these on my Google Maps, so I quickly can narrow down the options to what’s close by.

With all that said… one of the most important parts of the itinerary is planning in enough time to relax and enjoy the places you will be, and NOT overscheduling.  Kids will need naps and breaks. Heck, ADULTS will need naps and breaks.  If it’s not fun, then what’s the point?  So make sure to have lots of options for each day, but know that you will probably only hit a few.  The kids, and especially toddlers, will need time not only to nap but to play with their toddler toys and relax.