article, Family Travel, German Travel, Itineraries, Traveling

How to write an awesome itinerary!

One of the biggest challenges of being stationed overseas is creating a great travel itinerary. Most of my friends and I have become certified travel agents.(Only kidding,well kind of.) Creating travel opportunities that are diverse and memorable without getting burned out on seeing all 30,000 castles and churches in Germany can be a real challenge. (Insert glaze look over spouse’s face here.) A great part of our community is we are eager to share everything, the good, the bad, and the ugly. Also, with help from the internet, and Mark Zuckerberg/social media, and a few friends you can create some unforgettable trips.

Here’s how to start…

1) Time

Create some. One of the most common phrases we hear in this military life is, “it’s not written in stone, yet.” We know at a moment’s notice, literally, our plans can change because of awesome things like loyalty, honor and patriotism. Sometimes, there is frustration if you’ve put a great deal of time into your travel plans only to have to modify dates, cancel reservations or the worse, cancel altogether. 

Luckily, in today’s cybertravel world it’s easier than ever to buy trip insurance for flights, cancel car reservations and a few sites like and TripAdvisor have a “free” cancellation/change date policy. (see more information below)

Depending on how far out my trips are, I will carve out about 4-5 hours a week on building itineraries for my family. This helps me feel prepared and get excited at the same time. Sometimes I get lost on the internet or overwhelmed with TMI (too much information.) So I set a timer, literally and write up the important details of our trip with a notebook nearby.

2) First things first, when to go?

One of the first things I do is look at dates first. I check out my husband’s work schedule, the kid’s and school schedules, and any other conflicts. I keep a great calendar with a Sunrise app on my computer and phone (that I think is a little better than Google Calendar) because I can share with people who don’t have a gMail account.

The calendar lets me know if events conflict, when and where and for how long. After the dates are set I can then look for the destination. If I use the Trip*It app to book transportation and accommodations it’s automatically entered into my calendar.

3) Next up…Destination

Sometimes this is chosen before anything else. However, I have discovered it is better to choose the dates first, because although Italy sounds great in the summer, it’s not.  Io amo l’Italia (I love Italy) it’s incredible. I will visit six times this year. However, I don’t love Italy in the summer. Lots and lots of tourists, as well as, increased prices for almost everything and super HOT! We happened to be there in July last year and learned very quickly traveling in sundresses were not only pretty but a necessity. Since then, I travel to Italy in the spring and fall, they are perfect touring season!

Sometimes I do choose my dates and destinations together if I am researching a particular event. For instance, “the Running of the Bulls” in Pamplona is between July 6th – 14th. These special events are the center of the itinerary. Everything would pivot around that element.

TWW - Liguria sunset.jpg

4) Accommodations

Accommodations for family can be tricky, sometimes separate hotel rooms are more expensive than an Airbnb, Homeaway, or VRBO (part of Homeaway.) You may spend a great deal of your time on this step. However, if your family is just like mine, the most important thing is “INTERNET.” For me, it’s location to sites and uniqueness, and for my husband, how far from the airport/train station is it? and going through Marriott will sometimes have great cancellation/change policies, just be sure to read the fine print.

  • Check the cancellation policy BEFORE you book
  • Check to see what form of payment they accept (AirBnb now accepts AmEx & points) However, they charge immediately upon booking and accepting
  • Some hotels/B&B’s charge one night’s stay immediately and then the remaining balance after departure (this happened in England and Scotland)
  • Some require full payment prior to your trip (in my experience just in France)
  • HomeAway is billed right away typically in the currency of the property location (be aware of exchange differences)

Some of my friends have found amazing places to stay for the week or weekend including igloos, wine barrels, and I’m about to stay overnight in my first castle in Wildenstein, Germany that is also a youth hostel.

TWW - Parma B&B.jpg

5) Special moments

This is truly one of the hardest parts of writing the itinerary. We have five in my family and all of my children are very different. Our daughter Katy is an artist and writer, so she loves museums and art galleries; Christopher is a musician and song writer; Jessica loves to shop and cook. Meanwhile, Jon likes to discover cities and exploring without a plan.

To help with these diverse interests, I try to find at least one element for each child and my husband during our trip. I have found TripAdvisor and my absolute favorite, Like a Local guide, the most helpful when narrowing down specific subjects with local flair. I typically check to see how many reviews (if it’s uber-touristy) requiring pre-payment for tickets or my favorite. They are FREE.

When we were in Paris in November, we discovered the Shakespeare and Company bookstore, next to a specialty cupcake bakery, near the Louvre. Mom was a winner that day!

Remember, numerous museums are FREE in England, major bonus! Also in Germany, the Rathaus’s (courthouses) are free and are of exceptional beauty, inside and out, so don’t pass them up.

 Social media is also a help here as you can usually Google or Facebook what you are looking for and something will pop up. In Germany, if you type in the destination city followed by a (.de) most times it will lead you to a calendar of events for that town as well. There is always something going on in their calendars.

O.k with all these tips, I know that you’re ready to write your summer itinerary. If however, you are exhausted after just reading this, send me an email here at

It’s always an adventure when you ©Travel with Wendy!

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