How to Have Fun While Planning a Trip

Posted by on in Travel

Writer and travel expert Jeanne Ammermuller enlightens us on how planning a trip can be just as fun as the trip itself–if you do it the right way.

I planned my first trip in 1982 as a college student heading to a semester abroad. In a pre-internet world, I relied on two resources: Let's Go Europe and a stack of index cards.

With all that has changed, and all the added information available at my fingertips, those two staples still play an important role in any plan.
For me, trip-planning is almost an obsession; I start as soon as I have a spark of an idea for my next vacation. I revel in it, obsess to a point, and consider it almost as much fun as the trip itself. It can also extend a one-week vacation to months of happy distraction. So my advice is really geared to the trip-planner extraordinaire.


Let’s get this nasty beast out of the way. Budget ultimately will drive most of your decisions—will you stay in 4-star luxury, or are you looking for a safe, comfortable, cheaper option? Think about how much you can spend on transportation, accommodations, sights, and meals. I tend to lean toward lower-budget travel, but my approach should help no matter what your budget.

You can make a quick Excel table or word table where you can plug in ballpark estimates.

get a map

Whether you set up a Google map of your destination (just type in the city and voila, you have a great view) or decide to buy a quality map, I find it almost impossible to plan without getting a good understanding of the lay of the land. For cities, I have had great luck with the Streetwise series of maps. They are laminated, fold easily, and include transportation and key sites—and you don’t need an internet connection to find your way. This series now has multiple options for any city, including ones for just transportation and museums—although I’ve found those aren’t really necessary.

Use the map to try to find a way to organize the destination—if you’re visiting a country, divide it by region or city. If you’ll spend your time in a city, try to divide it by neighborhood or district—Paris makes it easy with the system of Arrondissements. New York can be divvied up by neighborhood. It will help as you plan your daily itineraries, so you’re not wasting time by traveling great distances or ending up somewhere without a plan for a meal.

Visit the Library

I know, it’s very old school, but for your initial planning, don’t spend your money on a guidebook—most libraries have a decent selection of guidebooks and can help you get the basics about your destination. You can also check out multiple books to get ideas and see which series most suits your style. Is it the highly-visual Eyewitness Guides, the thorough Rick Steves’ Series, or the very budget and alternative guide, Let’s Go? Libraries also can steer you to travelogues and memoirs of writers who can add a different perspective or excitement.

index card

My friends poke fun at my system, but they also have borrowed my cards for their trips and realize it’s not a bad way to go. I use the small 3×5 cards, and, with a rubber band, they can stay organized and fit in any carry-on.

I like the cards because they are portable both while planning and travelling, and they are flexible—you can add and delete easily. I keep them handy every time I do research, whether I use a guidebook, a website, or a suggestion from a friend. I jot it down on a card and decide later what I want to keep.

The basic system I use is:

  • Name of the attraction/accommodation on the top.
  • On the left corner I code whether the place is a: 'R'estaurant, 'H'otel, or 'S'ite.
  • On the right corner I indicate the area (city, section, neighborhood) I’ve decided on by looking at my map.
  • Just below I write the exact address and metro stop if it applies.

The rest of the content is up to you. I like to include hours of operation, cost, and a note about why I decided to write it down (remember, I start planning months in advance). I also write down the source—website, guide book, etc.—so I can go back if I need to reference.

The hours end up being very important, so you can plan your days around your favorite site. If the Louvre is closed on Tuesday, you may want to pick that day to go to Versailles—you definitely don’t want to head to the Musee D’Orsay that day as it will be mobbed!

So every time you find something interesting you may want to do, make a card and add it to the pile. And if carrying around a stack of cards seems too 90s, you can always take photos with your smartphone and have them handy that way.


When you’re ready to start narrowing down your itinerary, you can sort the cards by neighborhood and see what pattern makes sense. Make piles by city or neighborhood and put aside the places that no longer interest you and highlight the ones that are top priorities.

Next, copy a calendar, make one on your computer, or draw one by hand, making sure to leave lots of room under each day. Indicate your arrival day and time and departure day/time and then, using pencil, start sketching out each day.

You don’t have to get the list complete on the first shot—you can always adjust things as you go.

You can also see if you have everything you need for that day—do you know how you’re going to get there, how long it will take, where you’re going to stay, and, most importantly, do you have the names of a few restaurants you can choose from that are near your destination?

I’ll often put that list on a typed grid that I can slip into a transparent plastic folder, so I can reference it easily during the trip. But I also keep the cards and consider my itinerary very flexible. As I head out for a day, I only carry the cards for that neighborhood, and can go back and add something or pick my restaurant from the cards.

a note about meals

I’m not a foodie per se, but when I travel I cherish each meal. I only have so many meals in a certain destination, and I hate the idea I’ll end up wasting one on a sub-par meal. I find that last-minute meal decisions when I’m hungry and tired are inevitably a disappointment.

So I research restaurants widely, trying to find others’ favorites by using sites and recommendations. And if you don’t find a suitable place to eat at that location, then you know it’s a good day to pack a lunch.

So with my cards and grid complete, and one great guidebook in hand, I head off on my trip of a lifetime. When I return from my trip, I rubber-band my cards and put them with my guidebooks so I can share with friends or take a trip down memory lane.

jeane ammermuller

Jeanne Ammermuller is a writer by profession and a rabid traveler and planner when time allows. She’s traveled in Africa, Europe and North America–both solo and with children–and considers Paris and Kampala, Uganda, her favorite cities.


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