How To: Plan a Multi-Week Itinerary

When it comes to planning a multi-week itinerary for a trip - I'm in my element. 

I love planning and organizing. And yes, you may call me type A. So by extension this post is really meant for those of you that are also type A or for some reason want to be. By no means, is this the only way to plan an itinerary - it's just the way that works for me! My version of itinerary planning involves some level of certainty. The bottom line is that I like to know where I'm sleeping every night.

Does that sound like the kind of trip you like to take? Then read on and I'll take you through the my steps to plan a multi-week itinerary.

1. Start researching. Google. Search your favorite travel blogs. Read through a guidebook.

My Tips:

Lonely Planet Guides

Switchback Travel

Sunset Magazine (For the Western United States)

Pinterest - Some of my travel boards: Places To Go, Portugal & Southern Spain, Iceland, France & Spain, Norway

2. Write down the locations of all the things you want to see and do.

3. Use My Places on Google Maps and Create A Map.


4. Using pins, start mapping those things you want to see and do. If you want, you can use different pins for different activities or sights.

My Tips:

Since our trips are often planned around hikes - I use this great hiking pair pin. You can also include some additional description in each pin. For hiking, I like to include the length and details on wherever I found it, such as the page number of a guidebook.

5. When you're done mapping, hopefully you will start to see a pattern or grouping of the places you really want to go.

6. Start looking at the travel distances between these place and compare to how long your trip will be.

My Tips: 

I prefer to rent a car to travel - that way I can stop wherever I please and get out into the more rural areas.

I won't drive for more than 5 hours per day unless there is some special circumstance involved - like I need to catch a plane.

7. Start a day-by-day list for the length of your trip aka your itinerary. Start it with when you depart and when you arrive at your destination. Plan by travel days, cities, and any full day activities you have planned - such as a hike or tour.

My Tips:

Google Docs is great for this if you're planning for more than just you. 

When you arrive at your destination - plan at least 24 hours of downtime. Don't schedule yourself for anything. Recoup from traveling.

For my husband and I, 3-4 full-days, not counting travel days to and from, is a good number to spend exploring one place or area.

Let travel days be travel days. Don't try and schedule yourself by additional activities even it it's only a 2-hour drive to your next stop. Allow for unscheduled time to explore!

8. Now that you've got your itinerary, you can schedule anything else your heart desires!

My Tips:

The only thing I plan past our itinerary are the places we'll be staying while in each of our locations, I'll add this to the itinerary and map I create.

If there are any must-do-or-I-will-just-die activities that require booking ahead of time, I'll do that too and add it to the itinerary.

Do you have any good tips for itinerary planning?