Tools for Planning Long Trips: Where to Begin

This entry is part 1 of 11 in the series Travel Tools & Tips for Planning, Scheduling, Recording & Commemorating Your Trips

We have taken several trips that required a lot of planning to make work smoothly. I use several planning tools and applications to organize and schedule a long trip. These will allow you to enjoy the journey and limit the worry involved in traveling. I’ll show you how I use these tools for planning long trips, and that will help you understand where to begin.

One of the trips we took that required extensive planning was when we went to Scotland for six weeks. While there, we logged over 4,100 miles (yes miles, not kilometers). We went to Orkney, several western and southern islands. We drove some scary, narrow roads along cliffs of the north coast. In addition to the normal coordination of locating places to stay that are in proximity to the things we wanted to see, this trip required coordinating ferry rides where there might be only one ferry going to an island each day, making availability precarious and scheduling critical.

When we tell people about our mega trips, they always ask how we planned them. I think planning a long trip is a lot of fun and gets you vested in the trip, and you get to learn some history about your destination while you’re planning. So, here is part 1 of my posts about tools I use for planning our mega trips:

1. The first step is to learn a bit more about the places you want to visit in and around your destination. There are lots of options:
   • Obtain a guidebook. It doesn’t have to be a recent one. You can get one from the library, either in person or online. I like to collect them from our local Friends of the Library book sales.
     • Skim the guidebook and find things that look interesting to you. If you get a physical book, get some page flags and mark those things that require more digging, like location, reviews, and proximity to other sites you want to see.
   • If you can’t find or don’t want to read a guidebook, you can try Google searching for blogs.
     • As you find recommendations, you can use Pinterest to save them to a board. Then reference that board later on.
     • Or you can save them to Planapple, which is a Pinterest-like website that ultimately creates an itinerary for you. You can find more about it in the post I wrote about Google Maps, TripIt, and Planapple.
   • Google also has a feature called Google Explore. All types of information about a destination are captured on the website. Things such as flight costs, times of year to go, regional temperatures, and sites to see. So, it’s a pretty useful one-stop shop.
   • Another option is searching youtube.com for information about your destination. In this case, you’ll need to take notes for all the things you want to track.
   • You can also find TV shows, podcasts and videos about your destination.
     • For example, if you’re going to Europe, there are many videos created by Rick Steves that you can find on his website. You can also rent DVDs about your destination from your local library.
     • You might find that someone has done entire seasons about your destination, e.g., Stanley Tucci’s Searching for Italy. You can read about it online or watch it via a streaming service like Youtube TV.
     • I like to listen to travel podcasts as well because a lot of times there will be guest contributors who are from the area, and they can point you to the best places and things to do that are not widely known.
2. Once you have your list of places you want to see, you can start reading reviews of those places on your list. Look for the pros/cons, and good/bad reviews for each item on the list.
   • Tripadvisor and Google Reviews (you click on the item on the map and scroll down in the modal window to see the reviews there). Both of these sites are good sources for reviews. But make sure to read many reviews to get a representative sample.
3. Prioritize your list based on your research.
4. The next step is to map out where all the things are on your prioritized list. There are three options.
   • Many people like Google Maps, and in particular, the Places feature. There are limitations to using the My Places Maps, and it doesn’t create an itinerary for you. You have to use other tools in conjunction with the Maps to create your itinerary. I’ve described this process in my next post. It is still a good option if you have no idea how long you need to be in each place initially though.
   • If you do have some idea of how long you need to be in each place, you can use the free website called Scout Explorer. My post on that website is the third in this tools series. Scout Explorer does create an itinerary, but it doesn’t support the creation of a map that provides directions.
   • Another option is a service called Pebblar. Pebblar is a pay service, but it does create itineraries, and it supports integrations with three maps: Apple, Google, and Waze. I will write a separate post about Pebblar as I experiment with it. Update: that post is here in the series on Tools.