I’m clumsy, my spelling is atrocious, I suck at math and I’m a total slob, but people, I am really super-spanking good at writing a travel itinerary.  Here’ s what works for me:

• Research like crazy and keep a list.   No, I don’t mean a bucket list of far away fantasies, I mean a realistic list of experiences you want to have, and places you expect you can visit in the foreseeable future.  This should be tailored to your actual interests, not anyone else’s idea of “must see” places.  For example, my officemate at work loves soccer and film.  When he travels, he builds an itinerary around seeing his favorite soccer teams play and visiting locations of interest to movie buffs (like the homes of famous directors or set locations).  In between watching soccer and indulging in film nerdiness, he does the usual stuff: visiting museums, taking tours and trying local foods.

• Consider the length of your trip.  HOB and I have full time jobs, and given the complexity of our work schedules, our trips generally are about ten days long.  The shorter your itinerary, the more highly organized your itinerary should be.  If you’re taking a year off to backpack, well, first of all, let me pat you on the back—well done my friend!  You still should have an itinerary of course, but every day doesn’t have to be entirely scripted either.   But if, like me, you have a tight schedule and you are dying to visit a certain sight–you’d better know ahead of time when that sight is open, or you could risk showing up on the day’s it’s closed and you’ll be heartbroken.

• Remember how I taught you to find a cheap flight?  Well now it’s going to pay off.  Always keeping your travel list in mind, watch those airfares like HOB watches ladies in yoga pants.  Highlight places on a map that correspond with your travel list, and when you find a cheap airfare that will get you close, buy it immediately.   Remember, you can fly open-jaw (in one city and out another) to maximize your itinerary and airfare savings.

• Organize your itinerary by theme or region: for example, you could do “Opera House of Western Germany” or “Monasteries of Romania” or “Biking trails of Andalusia” or whatever floats your boat.  The point is you should have a purpose for each destination.   If you go to London for a week, don’t go to “see London”.   You couldn’t see London in a year.  Decide instead that you want to eat fish and chips, see the Rosetta Stone, and watch a different Shakespeare play every night.

• Now nail down your itinerary day by day and sort out where you’ll be spending the night.  Every travel guide I’ve read says the same thing: stay in one place as long as possible and make day trips.  Do yourself a favor and ignore this advice.  Here’s my updated and improved advice: pack light and spend the night.  Why?   Because there’s nothing sexier than spending the night in a series of smaller towns, throughout a regional area, next to stunning sights.  Here’s an example of a perfect travel day: HOB and I took a bus from Poitiers to Saint-Savin, France, population 353.  We checked into our “hotel” (a  €35.50 room above a bar) with a view out our window of the Abbey of Saint-Savin.  We spend the rest our day in and around the Abbey, gawping at it’s Romanesque frescos and picnicking on local treats. A kindly man kicks us out at closing time, and we take a last moonlit walk around the abbey, admiring it’s architecture.   At dawn we were munching pastries while waiting for our bus to our next destination, Chauvigny, a half hour away.  When you spend the night you get to own the town after the day trippers leave.  It’s magical.

• Sort out all your transportation connections well before your trip.  We travel exclusively by public transportation, and I almost always buy my train tickets in advance (fares are generally much cheaper if you buy them ahead of time).  Study a map with the connections and be alert for stopovers–places where you can stop for a few hours and then jump back on the train or bus to continue on your journey.  (It helps it what you want to see is close to the your transit stop.)

HOB and I travel every chance we get, so many of our trips pick up where a previous trip left off.  We’ve been tracking down Byzantine era mosaics from Ravenna to Rome and Sicily and on to Turkey.   We never pass up a chance to join the pilgrims at cathedrals on the routes of Camino de Santiago, or to relish a UNESCO World Heritage sight.  And of course,  I’ll never get enough of my major art crush: Romanesque architecture, sculpture and painting.  Wherever we travel, we try to visit the local market for regional picnic goodies and make it a priority to sample local street foods.  If we can find a concert or an opera we are extra happy.  Below are two examples of our most recent travel itineraries:

1. A ten day trip through Italy following the work of five Renaissance architects and urban planners (Bramante, Brunelleschi, Michelangelo, Palladio and Alberti) with side trips to see in situ works by Piero della Francesca:  Milan, Vicenza, Florence, Rimini, Urbino, Sansepolcro, Arezzo and Rome.

1. A ten day trip through Southwest France, focusing on Romanesque art and architecture, cave art, traditional markets and local cheeses: Albi, Rodez, Conques, Figeac, Souillac, Perigueux, Les Eyzies, Cahor, Moissac, and Toulouse.

You’ll get better at writing itineraries with practice–so make sure you follow my advice and travel cheap so you can travel more often!