Creating a Travel Itinerary

To be honest, the word itinerary makes me shudder. They are terrible, constraining, time-consuming, usually impractical schedules with the goal of making our travels easier. Except time after time, they will fail. That two-week trip will either feel like a marathon or a disappointment.

How do you balance seeing enough, without trying to see too much? You don’t. That is the best part of travel. You never know what the world is going to throw at you. You don’t know if it will be pouring rain when you want to hike the Cinque Terre trail, or if the museum is going to close for a private party, or if the president is going to die and the entire city is going to take to the streets.

The ultimate travel itinerary is one you are willing to forget about at the drop of a hat. Some would even say the best itinerary is the one that doesn’t exist. I agree, in some cases. My mother does not.

Here’s a few tips for when you need a plan, but don’t want your trip to end up like one of those seven-day, fourteen-country bus tours.

Stretch the Schedule

There is never enough time. Let me say that again. There is NEVER enough time. I don’t care if you have five years to travel. You’ll want ten. The key is to stretch the schedule as much as possible.

Have two weeks of vacation? Add weekends. Plan it after a holiday. Take sick days. Book a night flight. Whatever you can do to make your trip longer. Figure out the maximum amount of time you have first.

Do Research

Before you start putting down places and dates on a calendar. Research your destination. Document it well. Read travel guides. Talk to friends. Consult travel forums.

Figure out what looks fun and what should be avoided. Don’t forget to look for important events like festivals or holidays in your destinations. They can be both awesome experiences, and logistical headaches.

Make a good long list of what you’d like to see and do. And write down how long you’ll need to do it. Be realistic and always consult an expert for information. Then put the list in order by priority.

Get a Map

Now that you have a list of places to visit, get out the atlas. (Or head to Google Maps). Get a sense of where everything is, and how long it takes to get between locations. Check road conditions, and seasonal closures.

Plan a Route

Looking at your map, figure out the best way to get between your destinations. Are you flying in and out of the same city? Or can you go one way?

Does public transportation go to the places you want to see? Or do you need to rent a car or fly? Consider short flights for efficiency, but recognize they aren’t flexible with dates.

Add in Travel Time

Don’t forget that going from place to place takes time. Airports take time. Trains take more time. International flights can take days out of your life.

Remember that public transport often doesn’t have a schedule. It goes when it goes. And that may have nothing to do with your itinerary.

Flying to a new destination in the morning, then taking a train to a tourist site, then a bus to your hotel all in one day is exhausting. Count on travel days being an entire day. Don’t try to plan sightseeing on the same day.

Build in Flexibility

Unfortunately, the world doesn’t revolve around you. But don’t feel bad, it doesn’t revolve around me either. Something will go wrong. Planes will be delayed. Streets will close. Hotels will go out of business. There will be a festival or a riot or an election or maybe even a parade. You will have to cancel, reschedule, adjust, move and start over. Get used to it and just go with it.

Have time in your itinerary to deal with changes and delays. It’s just another part of traveling.

Build in Rest Days

It is important that rest days aren’t considered the “flexibility” time. Rest days are for resting. Doing laundry. Writing in journals. Taking naps. Drinking beer. Or recovering from drinking beer.

I plan at least one every week. In a good trip, we have three rest days a week. Don’t be afraid to have a day with nothing planned. They will often be the best days.

Ask Advice and then Ignore It

Travelers love to give advice. Look at me, I have a whole website full of advice. Listen to what others have to say. Call up old friends that have done similar trips. Post on forums like Lonely Planet’s Thorntree.

Ask what to do, where to stay, how long you should be there. Make sure to seek out others with similar travel styles. If you’re the adventurous type that likes camping and mountain climbing, don’t take advice from travelers who like art museums and five-star hotels.

Once you have all this information, ignore it. Well, most of it. It’s your trip, your adventure. You have to make your own decisions and create your own adventures. Don’t be afraid to take that itinerary and chuck it out the window.

• Next >