6 Easy Steps to Figure Out Where to Go on Vacation
The Steps I Use Every Time to Figure Out Where to Go
I struggled to decide where to go on vacation for a long time until I started following these 6 easy steps. Now I use these same steps for planning my own trips, planning trips for clients, and whenever friends and family ask me where they should go on vacation or if somewhere they’re thinking of is a good idea (I get asked that a lot).
Step 1: How Long Do I Have?
The first question I always ask myself is how long I have. This means counting from the day you can leave your responsibilities until the day you need to be back. This question has a couple of parts, but I never do any other research or planning until I know how long I can leave for. For me, this generally means how long I can leave work, but it also might mean working around other obligations. I ask this first because if I only have a long weekend I’m not taking an 18-hour flight. Or if I only have a week I’m not going anywhere that takes me two days to get to.
How long of a flight?
Part (b) to the question “how long do I have” is how long of a flight am I willing to take. And how many layovers. This is a matter of preference for everyone. Personally, I am willing to take up to a seven-hour flight for even just a long weekend, as long as at least one flight is a red-eye. I understand that I’m on the extreme end of things there, so if I’m traveling with anyone I always go with whatever they are comfortable with.
Will I need recovery time?
Part (c) to the question “how long do I have” is whether I’ll need recovery time on either end of the trip. Taking a six-hour, red-eye flight to get there is great, but if I need to take an entire day to recover before I can start my vacation or get back to work, I need to factor that into my plans. Flying north or south, when you’re not changing time zones by an hour or two may make it easier, but again, that’s something personal for everyone. For example, I do much better changing time zones by six hours than just one hour. I don’t know why, but changing by one hour throws me every time but if I change by six or seven hours I have no problems.
When I went to London I started planning that trip with an urge to get away, knowing that I could only take a few days off because it was a rather last-minute trip. Knowing I only had four days, I limited myself to a seven-hour, direct flight. I flew overnight on a Tuesday (so I don’t count that since I left after work) and back on Saturday (which was lost entirely to traveling). Flying through time zones didn’t bother me for this trip, because I knew I could take a red-eye on the way there and I would fly back on a Saturday, giving me all of Sunday for any recovery.
When I went to Savannah with a friend I knew my friend was not as willing as I was to take a long flight for a short trip. We knew we had a little less than a week, so I asked my friend how long a flight she was willing to take. She said 3-4 hours, direct, and we both also wanted to fly JetBlue. So those are the flights I started looking at. I found two places neither of us had been that had 3-4 hour, direct flights from Boston and came up with Savannah and Austin. I didn’t even have to go through the rest of the steps - I asked my friend because I was fine with either and she picked Savannah.
On the other hand, when I first thought of going to the Galapagos (back in 2019), I was thinking about a big summer trip, up to three weeks. For that long a trip I was willing to take a few days to get there and a few days to return, so Step 1 did nothing to narrow down my options.
Step 2: What am I Looking For?
Once I know how long I have and a general idea of how far I can travel, I think about what I’m looking for. The questions I ask here are:
Do I have something specific in mind? For example, when I went to London last year, I picked London because I wanted to see a few things I could only see in London.
Am I looking for an adventure? Sometimes I’m looking for an adventure. But sometimes I need to get away and unwind by not doing much at all.
Am I interested in a city, beach, mountains, or rural? I’m a city girl, so most of the time (especially when I’m traveling solo), I tend toward city destinations. But sometimes I’m more interested in the mountains or something more rural.
For example, when Norah and I went to Montana (instead of Galapagos because of COVID), I wanted to see a place I hadn’t seen before and somewhere different from my normal experiences. My comfortable place is in a city and most of my travel in the U.S. has been on the coasts. I had always wanted to see the mountains of Montana, but there were always more exciting places to go. We wanted to stay in the U.S., so I asked to go to Montana.
I remember when I thought of going to the Galapagos. I knew I wanted it to be a big, exciting trip and I started thinking about where to go next when I was only back from my trip to France for about a week. I knew I wanted something exciting, but I had no ideas other than that.
When I went to London, I knew I was traveling alone and only had a few days. So I wanted to stick to something easy for me. I wanted a city in a region (western Europe) that I was comfortable with and where I knew I wouldn’t stand out by being alone.
Step 3: What's the Weather?
This is an important question for me because I HATE the cold and will never travel anywhere that’s colder than the fall and spring where I live. OK, I shouldn’t say never because there are some winter destinations I’d like to see…. someday. On the other end of the spectrum, I also don’t want to go anywhere where the heat is so oppressive that I’ll be stuck inside all day. Personally, I would have trouble with every day being 100°F so I’ll never travel to Marrakech, Egypt, or even southern Italy in the summer. I leave those spots for the fall or winter.
For example, when I was looking for ideas when I picked Galapagos, I knew I wanted to go in the summer, so I excluded big chunks of the map where I would be miserably hot.
As I write this I’m deciding where I want to go next winter. I haven’t given it much thought yet, but I know I won’t be going to Canada, or any of the Scandinavian countries, or anywhere where there are freezing temperatures and a lot of snow.
Step 4: How Do I Feel About Crowds?
This is another personal preference. I have a real problem with crowds (my friends can tell you stories about how I’ve needed to leave stores and wait for them outside because they were too crowded). If there’s a place I really want to go, I’m more willing to put up with crowds (like when I went to see the Mona Lisa). But especially when I’m looking for a relaxing vacation, I’ll look for spots that don’t have the overwhelming summer crowds.
For example, when I picked London I knew I would be traveling at the beginning of May and crowds wouldn’t be an issue. That opened up a lot of choices for me to pick from.
Another example is when Norah and I picked Montana, I nixed anywhere there would be a lot of crowds (well, we did go to Yellowstone one day, but Norah magically navigated us away from the worst crowds).
Step 5: Use Google Maps!
I open Google Maps, scroll waaaaay out, and start looking around. I draw an imaginary circle around Boston (if I could find a way to draw a literal circle, I would) and start seeing what destinations fit with my answers to all the questions I’ve asked myself. This might take a little bit of research, if, for example, Berlin would be a great spot to add to my list, I’ll do a very quick search of Google Flights to see if there are any direct flights and how long the flights are (both direct and with connections). In this step, I narrow my choices to five places or less. Ideally, I get it down to two or three, but five will do.
When I picked London for a long weekend, my imaginary circle was smaller because I wanted a seven-hour or less, direct flight. I also wanted to leave the country, because sometimes I just get an urge. That left Western Europe and Canada. I went to Quebec City the weekend before, so I focused on Western Europe
When I picked Galapagos none of my other questions had narrowed my choices all that much. I was willing to travel anywhere, except where it was too hot. I didn’t know if I would be traveling solo and didn’t care whether there would be crowds, I just wanted somewhere exciting. I picked the Galapagos by zooming way out on Google Maps, and did the equivalent of spinning a globe and letting my figure pick the place. I swiped my mouse and looked at where it landed. It landed on Central and South America and I thought: Galapagos!
Step 6: Research
Finally, once I have a manageable amount of choices, I start researching. I look at what the prices are (to get there and to stay there), what there is to see and do, how friendly it is for solo female travelers (if I’m going alone), what kind of food there is (this won’t put me off a place for forever, but it might help me decide between two), whether I would need to rent a car, and whether there are any day trips or other places nearby I would want to visit.
This isn’t extensive research, this is just helping me decide where to go. I don’t start my crazy, in-depth research until I’ve decided where to go.
For example, when I decided to go to London, I narrowed down my choices to Dublin, London, Paris, Amsterdam, and Copenhagen. I had been to Copenhagen and Paris in the last few years, so they were further down my list. What drew me to London were the museums - I really wanted to visit the London museums, especially the British Museum. Then I checked prices, which were surprisingly reasonable because I went the week after King Charles’ coronation.
When I decided to go to the Galapagos I skipped this step entirely. It was a bucket list trip, so I knew I would save whatever money I needed and do whatever else I needed to make it work. I didn’t care about the food or anything else, I wanted to see the Galapagos and I made it work.
This entire process doesn’t take long! I usually get through Steps 1-4 in just a few minutes (figuring out where to go next winter is taking longer because I haven’t sat down to make a decision, I’m still letting the idea percolate). Step 5 takes anywhere from five minutes to an hour. Step 6 depends on how well I’ve narrowed down my options, but it usually only takes me a couple of hours.
Want a google doc to help you decide where to go next? Download it here! You can print it or use it in google docs.
