My Travel Planning Process

Summer is quickly approaching. As I’ve been chatting with friends, family, and colleagues about traveling, in addition to doing some of my own travel planning, I thought it might be helpful to share my process, including, tips, strategies, considerations and mindsets that go into it.

Know Your Travel Style (And The Styles Of Anyone Traveling With You)

Plan Up Front, Reap The Benefits Later

Don’t Plan For Everything, Do Plan For Anything

Phase 1: Research, Research, Research

Travel is always on my mind, and I’m constantly thinking about my next adventure. It’s the thing I love most. My lifestyle is designed to support it. I’m not a nomad, but I do like to travel for extended periods of time, typically 1-3 month stints. This affords me the opportunity to save money, see more, experience local, and work from the road. I like to try and do at least 1 international trip a year and two domestic trips, typically involving a road trip that includes nature, camping, and urban activities. For inspiration, I subscribe to multiple travel newsletters/blogs and make use of the library for travel books. My two favorite blogs are Nomadic Matt and Be My Travel Muse. Lonely Planet and some other off-the-beaten-path books are very comprehensive, especially for countries I’m less familiar with. I stopped reading Fodors and Frommers which I used to like but now find the content a bit touristy, though they are great if that’s your style! Rick Steves is somewhere in the middle. And of course, general Internet research is an excellent resource, especially blogs, YouTube, and tourism websites for a given destination.

This phase typically takes me a few months for longer trips. I like to first brainstorm ideas, let them settle in my head and for the unconscious to process, then iterate. While I always appreciate input from friends and family, I tend to prefer my own research exploring what’s out there, catered to what I enjoy doing. Plus I find it highly energizing and inspiring. I absolutely love planning because it gets me very excited about a trip, and just in general puts me in a good mood.

Phase 2: Organize & Estimate

I use Google Maps quite extensively, until I find something better, to mark places of interest on the map. This makes it really easy when I’m actually in a place to see where things are located. This helps me can plan my day by visiting things that are in close proximity to each other. You don’t really need Internet if the maps have been cached (downloaded) to your phone, so you can navigate yourself around manually if necessary. There are other offline map tools, though I haven’t needed them.

I then create an Evernote note, another tool I use extensively and continuously, to capture a TODO list of things to see & do, food & drink, nightlife, events, and other notes & details for a place. I’ve become more detailed with these as I use them to write blog posts when I return home. In fact, my blog posts are almost an exact copy from my notes.

For road trips, I then use Roadtrippers, which is the greatest, to create a skeleton itinerary of the main places I want to go. This is not only a fantastic way to visualize the trip, but Roadtrippers also gives you the most efficient route. It will tell you total miles, total time, miles between places, time between places, and cost of gas based on your vehicle. I highly recommend signing up for Plus (subscription) which is inexpensive and offers more waypoints.

I then create a spreadsheet where I lay out (roughly) how many days/weeks/months I want to travel for and begin filling it in. First I’ll see roughly, based on research, how long a particular place (i.e. city) will take to do what I want (or relax). I’ll list everything out to see about how many days are needed. Then I’ll reference Roadtrippers to capture the time it takes to travel between places. This is really important because if it takes say 6-8 hours to drive or bus somewhere, you’ll need the next day to actually do the thing you want to do. So you now need two days for that place. In the past I’ve often underestimated the time to see things when the time to get there was significant, so this solves that problem. Sometimes if a place lacks things to see or do, and doesn’t take more than a couple hours to get there, I’ll use two half days to make up a full day. For example, drive there and arrive by noon, leave the next day in the afternoon. This works really well because you can allow time for unexpected encounters on your road trip, delays in public transportation, and have the ability to experience both day and night.

The most important things I capture during this phase are dates, places, the city/town to stay overnight, what I’ll most likely be doing during the day, departure/arrival cities, travel times, and any additional notes. Sometimes I will estimate the cost up front just to see how much I’ll need to budget/save. It’s pretty easy to do some quick “back of the napkin” math. Then I go back and edit the spreadsheet to incorporate additional research, thinking, and bookings to capture the actual cost. You can download my spreadsheet template.

I never track food because I think it’s a waste of time. I simply get a sense of food costs and estimate the average cost per day multiplied by the number of days I’ll be in a place. This is close enough and helps me take food into consideration in my budget, but doesn’t require spending a ton of time keeping track of all my receipts and over planning. The way I look at it is that I have to eat regardless, whether I’m home or traveling, so I only really need to know the delta. For example, Iceland (and Scandinavia in general) is incredibly expensive for food, so that’s important to know and budget for. I also tend to book places with kitchens so I can shop at the grocery store and cook instead of going out to eat every night which saves quite a bit of money.

The last thing I track are activities. They usually don’t impact the overall cost that much, unless you’re on a shoestring, so I only capture what I definitely want to do. Excursions like glacier hiking, scuba diving, and other things like that are worth capturing because they may actually noticeably increase the overall cost of the trip.

I tend to like to go go go and be as active as possible, partly because I want to see and do everything, but I also I like the personal challenge. However, that only lasts for so long and gets harder as you get older. By spreading out your time in a place, you can spread out your energy and not have to cram so much in. This also allows you to enjoy things more. As a side benefit, I’ve found I remember things more clearly since I’m not doing so much so close together, making it difficult for your brain to separate things. For every week, I will budget a day or two to either relax or do something that is low effort in order to recouperate. For more tropical destinations this is usually sitting on a beach reading, or if it’s a park where there has been lots of hiking, sitting in a hammock reading.

Phase 3: Iterate & Incorporate

As I mentioned, I like to plan in advance and continue researching, brainstorming, and talking my trip through with friends or family to help me think. Then I go back and update my plan. It usually takes me about 3 iterations to get to the final itinerary. For me this is hugely important because the best plan is typically not the first plan, so allow some space to learn, think, and adjust.

Phase 4: Book It

Once plans have settled, it’s time to book! On trips a month or less I usually book just about everything since it’s easier and cheaper, but on longer trips I try to only book a week or two in advance.

I first look at flights which tell me where I’ll need to look for accommodations. It’s not always obvious where airports are in an unknown land, or which might be cheapest or easiest. This is important because you may not be able, or it might be cost prohibitive, to fly directly to where you ultimately intend to go. With accommodations, especially for parks, you may have to stay in a nearby (or not so nearby) town due to price or availability. In general, book as much as you can in advance, but don’t finalize your plans until you’re happy and confident with the plan. If you travel in shoulder seasons or to less popular destinations, especially during weekdays, it’s much easier to book things on the fly. I tend to book flights first, as doing so well in advance will help save money and starts to finalize the itinerary. I definitely recommend flying mid week and/or Sat where flights are typically cheaper.

Next, I look at accommodations, starting with the most popular or longest stay since those are the most important to get right and ensure availability. I use AirBnB primarily these days, with Booking.com as my secondary. Agoda is great for Asia. Sometimes I’ll go for extended stays if available and camping where possible. I tend to avoid hostels unless I can find a nice one with private rooms. I’ve tried, but simply can’t sleep in a dorm. Too noisy, too much motion, and I need quiet, solo time at the end of the day to recharge. For me, sleep is crucial in being able to enjoy my trip, so having my own space is a requirement. In Europe and Asia I have stayed in some fantastic hostels with private rooms which are awesome to get the best of both worlds, your own space and the ability to interact with other travelers.

Something I do when looking for accommodations is to filter based on the lower end price I want to pay. I do this so that if I can find something that meets my needs at a cheaper price, I won’t be tempted by more appealing options that cost more. Accommodations make up a large percentage of a trip’s cost, so unless staying with friends or family for free is an option, then any opportunities to save money should be done. That said, don’t compromise on what you need to be comfortable to enjoy your trip. And if working, ensure you have the quiet, creative space with strong, stable Internet to support that. Be mindful of cancellation policies. Booking.com has an edge in this regard because you usually have free cancellation. AirBnB is overall better, but some cancellation policies are strict while others offer refunds, though you’ll have to eat the service fee regardless. For longer stays, this is significant.

Lastly, I book excursions, as they can easily fill up. Some, particularly museums or tours, require advanced reservations. It’s also advisable to book in advance simply to avoid crowds. With COVID-19, more and more places require timed entry, though that may change back to normal in time. Regardless though, if you know you definitely want to do something, book it! Check cancellation/change policies in case plans change or the weather is bad.

Phase 5: Manage It

While I use the respective booking apps for accommodations to retrieve details, TripIt is my one stop shop for itinerary management. You can manually add all of your trips, plans, booking receipts or forward to plans@tripit.com from the email you sign up with and in most cases those bookings will be automatically added to your trip. You can also share, add to your calendar easily, or plan for someone else. It’s great, and I’ve been using TripIt since 2013. You can also store passport and/or trusted travel numbers for easy access. One nice touch I like is the stats it tracks for how many cities, countries, miles you’ve traveled (42 countries, 274 cities, 302,588 miles as I’m writing this). It’s fun to reflect back on, and it inspires me to keep going. Not that I need it.

Hopefully this has been a helpful read, let me know your travel process!