I’m starting to think through my travel plans for 2015 and I thought I’d share a behind-the-scenes look at the process with you. My trip planning style varies a lot depending on how last-minute the trip is and whether I’m traveling solo or with friends. For the most part, though, if I’m looking to get an idea of what my options are and how much I have to start saving up, this is what I do.

1. Figure out all the possibilities.

Add to Map

This is my absolute favorite part and it’s crazy simple. It boggles my mind that Google doesn’t make this tool more prominent. Just head over to Google Maps and create a new map. Type in the name of a place you’d like to go, and search. Once it’s zoomed in on the map, click “Add to Map”. Rinse and repeat until you have every place you can think of pinned into the map. Don’t worry about colors or anything. Google’s default red pin will do just fine for now.

I also like to look around the area that I just pinned for other cities that might be interesting.

2. Group them together.

Red Pin Map Once I’ve pinned to my heart’s content, I zoom the map all the way out so I can see the continents all together. This is where I start to look for groupings that could turn into logical trips. I could easily group Ireland, Northern Ireland, and Scotland in the same trip. And I know budget airlines would make it easy for me to do an Australasia trip that groups in Singapore, Indonesia, Australia, and New Zealand.

When these groupings start becoming clearer, I give them colors. I tend to use the bolder colors for major cities that I want to include in the trip and then its lighter counterpart for the “maybe if I get there” cities that I want to keep in mind.

The map stars to look something like this: 2015 Travel Planning Map

Here you can see that if I wanted to visit all the places on my map, I have at least 7 longish trips ahead of me with lots of smaller ones in between.

Pick a region.

UK and Ireland

Once I’ve identified my trip groupings, I zoom in on one that is the most interesting to me at the moment. In this case, I saw a really good flight deal to Dublin come through my Twitter list over the weekend and it has me seriously considering a trip to Ireland and the UK. For this trip, I know I’ll need a flight to and from. That airfare deal was pretty good, so it will probably be my best bet, but I’m also going to look into the option of an open jaw ticket where I fly into Dublin and out of Edinburgh. Maybe it’ll be cheaper? Doubtful.

I also know I’ll probably need a flight between Belfast and Glasgow since I don’t plan to rent a car (driving on the wrong side of the road + still not knowing how to drive a manual transmission = not a good combo for renting a car in this area). Transit between the other cities should be pretty easy over-land, but I’ll need to research those too.

I’ll also look into the possibility of adding London into this trip, but it’s kind of out of the way and there are steeper taxes flying into and out of London, so it probably won’t be kind to my budget. London will probably be left out for another trip.

You may dream of going to South America in the spring or want to hit the highlights of Europe. Just make sure you pick something reasonable that doesn’t have you zigzagging around the globe! I also go through this process for trips to specific regions. I’ll just pin a lot of cities within that region and then narrow down from there.

Estimate expenses.

Here’s where things start to get spreadsheety. I fire up my trusty Google Docs and start to fill in the skeleton of a budget: flight, accommodation, food, etc. I have a spreadsheet for every trip I’ve taken over the last 5 years, some more complex than others. I also have a bunch saved for trips I haven’t taken yet but have already researched. Spreadsheets make me happy, as long as they’re travel spreadsheets.

There are 5 major expenses that make up the budget of any trip:

  1. Flight to/from
  2. Accommodation
  3. Food
  4. On-the-ground Transit
  5. “Experience” Expenses

Travel Planning Spreadsheet Figuring out the first 3 is pretty easy.

Flight: You can get an idea of what your flight will cost in any number of places. The simplest for your standard round-trip fare is to just plug it into Expedia or Hipmunk and choose one of the flight prices. This works best if you know what time of year you’re going on your trip. If you don’t know, using something like Skyscanner’s “this year” option will let you see a graph of prices over the course of the year and you can make an educated guess.

Accommodation: Next up is a place to rest your head at night. Couchsurfing or hotels are always an option, but I prefer hostels. I load up Hostelworld, type in the city I’m visiting and some approximate dates. I usually like to stay at least 3 nights in a city, so I choose a 3 night booking and then scroll down through the results to get a rough average of what the nightly cost for a hostel in that city would be. I plug that number into my spreadsheet for reference and multiply it by the number of nights that I’ll be in that city. I like to keep the numbers separate so I can adjust once I get a better idea of the schedule for my trip.

Food: This one is based on experience and knowing how to eat cheaply, but I budget $30/day for most major cities unless I know a place is notoriously expensive (I’m looking at you Oslo). If I were going to a destination where the exchange rate is greatly in my favor (i.e. Southeast Asia), I would budget a lot less for food per day.

I rarely hit the $30/day mark, but there are some days that I might spend $15 and others that I might meet up with a friend or go out for drinks that could add up to $40, so it would average in the end.

On-the-ground Transit: There are 2 things to consider here. First is your day-to-day transportation. Are you visiting London, Tokyo, Hong Kong, etc. where you’ll need a public transit pass? Or are you going to maybe Amsterdam or Copenhagen where you could get around on a rental bike for the day? Maybe you’ll just be able to get everywhere on foot. A quick Google search will tell you the rates for daily or tourist transit passes for that city.

Rome2Rio options

The second piece of this puzzle is your transit between cities. If you’re going to more than one place over the course of your trip, you’re going to have to factor in the costs to get between those places. This is easiest when it’s built into your original airfare (hello multi-city tickets), but I’ve found the cheapest route is generally to use budget airlines or trains or buses when they’re available. To get these numbers, I live by Rome2Rio.com. Just plug in your starting city and ending city and it will tell you all of your transit options between the two places from planes to driving yourself. You’ll be amazed at what you’ll find!

“Experience” Expenses: These are your museum admissions fees, your guided tours, etc. Depending on your goals for the trip and your travel style, this is where your budget can go wild. If you’re planning to take diving classes or go bungee jumping, you’ll definitely need to account for that here. If you’re planning to play it by ear, which is what I tend to do, I get a rough estimate by multiplying a reasonable number (it’s generally whatever my daily food budget worked out to be) by half the number of days in my trip since I probably won’t be doing something that has an admission fee or similar expense every singly day. I like to keep a tight budget, so that number helps me make sure I’m not over-spending, but if you’re not used to your travel style and potential expenses, it might better to multiply it by 2/3 or even account for a daily budget.

Repeat For All the Groupings.

Once I’ve sorted out the budget for one of the pin groupings, I move on to the next one until I’ve covered the majority of the trips that are on my “must-do” list. That’s when I add the big number together to see what all of my trips will cost for the year. At this point, depending on how feasible the number is, I may start to weigh the trips against each other: which ones are ones I just have to do this year vs which would just be a fun addition? Which ones are great bang for buck? Can I move some to different times of the year to avoid peak season? It’s pretty unlikely that I’ll be able to go on all of these trips, so it’s helpful to have the information I need to pick and choose from.

Alternate Routings.

I can get a little OCD when it comes to booking more complicated trips like the Australasia one I mentioned earlier. In that trip, each segment is its own little puzzle to solve and figuring out the optimal starting and ending points in order to keep airfare at a minimum involves trying a lot of different options. Getting the answers to questions like: “Is the best route Sydney->Melbourne->Christchurch->Auckland? Or maybe it’s Melbourne->Sydney->Auckland->Christchurch. Or maybe it’s actually Melbourne->Christchurch->Auckland->Sydney in order to get the best flight home. It turns out that the cheapest permutation is actually Melbourne->Sydney->Christchurch->Auckland. Sometimes these things can take a little while to figure out, but you can end up saving hundreds of dollars and many hours of flying!

Time to Book.

Just because you have your budget in place, doesn’t mean you should go straight off and book. Unless, of course, you’re flying out in the next 2-3 weeks. In that case: what are you waiting for?

If, however, I have time to spare, I like to wait a few weeks and keep an eye on airfare deals for the cities in my trip to see if anything changes from my original estimates. If you have enough time before the trip (more than 3 months), odds of the price going up are super slim. Odds of it dipping, even just a little, are decent, though. Or maybe there will be a special to a city in your trip that you didn’t originally plan as your start or end point, but the fare is too good to pass up. That gives you plenty of time to rework your route to take advantage of the new fare.

When I’m comfortable with the current rates, I pull the trigger. For airfare, I like to book through Expedia because I get to double dip and earn Expedia+ points. Unless I know I’m traveling during a peak time (a festival, or summer in Europe), I tend to just book my main flight and my first few nights at the hostel. I’ll save booking the rest of my hostel nights and other transit for when I’m actually on the ground and have a better idea of what I plan to do. This leaves me room to change my itinerary if I can’t get the budget flight I wanted, or if I fall in love with a city and stay longer, or I hear about a great hostel from a fellow traveler. It’s all about flexibility for me.

And Go!

That’s it! Once that’s all done, I might spend some time looking up cool things to do in the place I’m visiting or booking any major excursions (o hey there safari I won’t get to go on because they were all booked out by the time I stopped procrastinating), but mostly I just wait until I get there and speak to locals and fellow travelers to get tips on the best ways to spend my time.

Need help?

I love helping people plan their trips. Leave a note in the comments or get in touch if you want some help planning your next adventure!

I’m always looking for new tips to improve my trip planning process. I’d love to hear about how you plan your trips! Add your favorite tools in the comments below!


A few hours after I posted this, I heard about an amazing airfare sale and nabbed that trip to Ireland and the UK! Check out the details here.