Recently, I shared our Costa Rica travel itinerary with a colleague, and she was blown away by the amount of detail and planning it included. It never occurred to her to plan an itinerary before a trip — she just noted places to see and things to do and went from there. This sounded all too familiar, as it was how I traveled years ago when I was first starting to explore the world. I would just show up and let the travel happen…
This got me thinking about itineraries. Austin and I love them. We never travel without one. We have a whole shared google drive folder to store our plans, split out into completed, upcoming and potential trips.
I’ve noted before that, to me, an itinerary is freedom. By planning things out, we don’t waste precious travel moments with the hassle of just-in-time logistics, waiting in lines, or being disappointed because a restaurant or museum is closed.
There’s an art to creating a detailed but realistic travel itinerary — one that’s considered, but not over-planned. Here, I break down the steps we take and share our resources to help you plan a better holiday. It seems like a lot of work, but I say planning a trip is half the fun!
Aside: Austin and I share the task of travel planning in our family, but this is very achievable as a one-person activity!
Before we start to think about building an itinerary, we’re taking care of the macro planning that lets us assess our travel calendar beyond one specific trip.
Blocking Travel Dates & Anticipated Expenses
To make the most of our travel planning, we keep two yearly travel documents.
The first outlines statutory holidays and tracks vacation days for the year (my husband works in academia with a flexible schedule, so my vacation tends to dictate our travel dates). We pencil in tentative destinations and trip lengths, always considering cultural events and local festivities to either avoid (e.g., Ramadan in a Muslim country or some European cities in August when everything is closed) or take part in (e.g., Mexico during Dia de los Muertos or Nuit Blanche in Paris). I also have a good sense of my boss’ travel schedule about a year out (a perk of having a fellow travel-loving boss) and note those dates to avoid being away.
As much as possible, we research and all-but-book flights right before requesting vacation time to snag the best airfare, which sometimes means leaving on a non-standard day of the week. We also try to make layovers work in our favour, staying a couple nights to explore a layover city if fits our plans and doesn’t add significant expense or logistical complexities.
We’re always seriously looking six to 12 months out, but right now we have calendars up to 2018 very tentatively sketched — mostly to remind ourselves of fixed travel dates like weddings and statutory holidays as we plan.
Aside: this pre-planning works whether you have two weeks or three months of vacation in a year, because seeing everything in one place helps to budget precious days more efficiently… That way, it’s not suddenly November and you realize you’re out of vacation.
Here’s how our completed tracker looked for 2014:
|Days Used||Days Remain||Destination||Dates|
|-3*||28||Start: 28 Vacation Days|
|1||27||Windsor||Jan. 31-Feb. 3|
|1||26||Dallas, TX (Family Day)||Feb. 14-17|
|9||17||Riviera Maya, Mexico||Feb. 18-Mar. 1|
|2||15||San Antonio, TX (Conference)||Mar. 20-23|
|4||11||Longboat Key, FL||Apr. 4-9|
|0||11||Windsor, ON (Easter)||Apr. 18-21|
|2||9||New York City, NY (Canada Day)||Jun. 27-Jul. 1|
|1||8||Portland, ME (Civic Holiday)||Aug. 1-4|
|0||8||Windsor, ON (Labour Day)||Aug. 29-Sept. 1|
|6||2||Paris, France/Reykjavik, Iceland||Oct. 3-14|
|0||2 days carryover||Niagara-on-the-Lake, ON||Nov. 8-9|
*vacation days carried over from 2013
The second document is a spreadsheet that tracks our estimated and actual annual travel budget. Because travel represents (by a wide margin) the largest portion of our discretionary spending, we track this much more closely than other variable expenses. For each planned trip, we note costs for airfare, accommodations, car rentals and excursions as they are paid for, and anticipated costs for things like meals out and incidentals. This document is SO helpful because it shows our year of travel expenses at a macro level (a rule of travel: you always think you’ll spend less than you do!). If one trip is shaping up to be really expensive we will adjust elsewhere to keep our budget roughly in check.
Pinterest has been essential to our planning process, especially because I process information visually. Before the days of this tool, my pre-planning for travel was housed in a leather notebook with scraps and printouts and handwritten notes from travel magazines and articles about places I wanted to visit, divided by country and city. It was, in a way, my totally inefficient analog Pinterest, bolstered by 1001 browser bookmarks. I planned dozens of successful trips this way, but looking back, what a hassle! Today, a few Pinterest boards replace my old paper system:
First — an overarching future travel board. This hosts anything that catches our eye for future travel and has hundreds of pins.
Second — unique boards for planned trips, for example, this board for an upcoming trip to Marrakech, Morocco. These boards get created only once plane tickets have been booked and vacation days confirmed. I do a Pinterest search of all my boards for that location and move over existing pins (this process is now SO much easier!). From that point forward, any article read or resource found about a destination goes on this board. If a friend mentions a place or I read about something in magazine, I find a relevant pin and add it to the board. This way, everything is in one place. No scattered bookmarks, emails, paper scraps or stacks of magazines to sort through.
Third — cleaning up as we go. At the end of each year, I move pins from each completed trip over to my “favourites” boards for sites we visited, and to my “future travel” board for sites we missed (next time!).
Building the Itinerary
A problem many people run into is to stop at the information-gathering stage. A list of things to do or collection of pins isn’t helpful without researching locations, hours and other logistical miscellany. So, we build an itinerary. This is our trip bible and we take it everywhere.
Aside: today, there are a plethora of online itinerary building resources and apps out there such as TripIt and Tripomatic, but I haven’t found any that compares to the full control, customization and ease of a simple google doc.
Here’s our current master travel itinerary. This document has been refined over dozens of trips with new learning incorporated each time. The original version was what most of us probably start out with — a list of places to see and eat — but has evolved into a super-helpful living document! Here’s how it’s organized:
The top of every itinerary includes basic details about our destination: the currency conversion (to both USD and CAD), tipping customs, time zone, average temperatures and sunrise/sunset times for our month of travel. This helps us budget, know what to pack, and prepare to stave off jet-lag.
The first section is a little calendar that shows our itinerary at a glance — the city we’ll be in, accommodations and a rough outline of planned activities. Think of it as the refrigerator calendar summary.
Flights & Accommodations
We refer to this section 100 times during our travels. It’s shockingly helpful for filling out customs forms, catching flights, giving cab drivers directions and (sometimes) when we get lost, to have all crucial details in one safe place. Don’t forget the airport terminal number! We’ve done that once or thrice and had to shuttle between them.
A Google Map
Austin creates a google map for every trip we take. It helps us to visualize clusters of sites and restaurants to plan our days, and can be printed to keep back-pocket for navigation. Here’s a sample from a recent trip to Paris. We colour code restaurants, sites, museums, bakeries and other categories of attractions for easy reference.
Detailed Daily Itinerary
This is both the most and least important part of the itinerary. It’s where we do the work of planning. Austin and I pull up all our links, maps and notes and start figuring out what goes where, like a little puzzle.
Some questions we ask as we plan:
- Are any museums or attractions closed on certain days? In Paris, many museums are closed on Mondays.
- What time do the locals eat? In parts of Spain, you get funny looks if you try to eat dinner before 10 PM.
- Do any restaurants require reservations well before our visit? I like fine dining — many starred restaurants require reservations months in advance.
- What are our top sites/restaurants to see and try, if we have to choose just a few? This ensures we plan the most important stuff first and don’t overload our itinerary.
- Will we be staying in one city the entire time, or taking day/overnight trips from our home base? This may affect the accommodations we book, whether we rent a car, or whether we choose to stay in a hotel or Airbnb.
As we ask these questions, we start to see patterns… A museum that is slowest on Wednesdays near-by a restaurant we want to visit for lunch. A day excursion that fits best on a Sunday when many things are closed in the city. An overnight trip to a close-by town that will change how we book our hotels… and so on. The itinerary begins to take shape.
Everyone’s travel preferences are different, but the below tips work for us:
- Do not over-schedule! This is my biggest tip. Austin has a mantra that “we’ll be back someday,” which helps us to avoid burnout from trying to do too many things on too little time.
- Spend at least a few days in each place. There’s a temptation to want to visit as many different places as possible in one holiday — I resist it all the time as I research! But our approach goes back to Austin’s “we’ll be back someday” mantra. I’d rather spend a sustained chunk of time in one place getting to know its charms and quirks than two frenetic days rushing from site to site just to say I was there. (I know a couple who recently did 4 countries in 10 days — that sounds terrible to me, but do what works for you!)
- Limit “fine dining” meals (i.e., multi-course options) to one per day to avoid taste fatigue. We also try to do lengthy meals for dinner, instead of lunch, to avoid missing out on several consecutive prime afternoon hours of site-seeing.
- Limit museums or intensive cultural sites to one a day, to avoid sensory burnout.
- Try to visit busy attractions (think: churches, museums, key tourist sites) on non-peak days to avoid crowds.
- Keep activities clustered in a neighbourhood or area of town to avoid wasting time on transit and to walk as much as possible.
- Try to hold a couple interchangeable “free” days without any formal commitments to account for unexpected bad weather.
- Build in down time. Leave stretches of time with nothing planned to recuperate. We are all about the holiday siesta!
- Account for 25% more travel time than google suggests. Roads are closed, you get lost, conditions are bad, stuff happens.
Once we’ve tentatively scheduled the itinerary, we split up tasks starting with the most important ones — making our coveted restaurant reservations, buying tickets to attractions we really want to see — and build out from there. If we start to feel information overload (it happens!) we step away and come back later.
Aside: We exclusively use a Skype subscription for our international calls in order to keep costs low.
Part of the fun of a trip (I would venture) is getting familiar with a new (or reacquainted with an old) place before even stepping foot on its soil.
A few key local details that we always research:
- How does local transit work? What’s the best way to get to and from the airport? Is there a subway? How does fare work? What are the main transit lines? Do people take taxis? Is it safe to walk after dusk?
- Commonly used phrases and terms. I speak three languages, which helps us get around pretty well abroad, but even in foreign-to-us tongues, we like making the effort to learn a large handful of key phrases, however terrible our accents. It goes a long way to cultivate respect as a visitor of a new place.
- Similarly, we look into local customs, such as standards of dress, the predominant religion and holy days, and any cultural taboos.
- The local foods and specialties. The fun part! We make a list of local dishes to try and the best places to find them, crossing them off as we go. On a recent trip, my brother-in-law and I had a laugh going through a list of unusual fruits and trying to find them at the market (and got my mom-in-law hooked on soursop fruit!).
Using the Itinerary
An itinerary is no use if it doesn’t actually help when you reach a destination.
Ours gets printed and kept with us at all times as our at-a-glance reference guide. During the trip, usually in the evening before heading to bed, we take a look at upcoming plans and adjust as needed — moving things around, adding activities or cancelling as needed to fit our moods and preferences. We’ve been known to clear a whole afternoon for a siesta. That’s the beauty of vacation.
A tip: always include addresses! When abroad, we often don’t have internet access on our phones, so including a full address has saved us many hours of wandering to find a place, or expensive emergency data plan use.
I want to emphasize that an itinerary doesn’t dictate what happens. It is ripe to abandon if we’re in the groove of a trip and decide to change course in the moment. This is so important. Many of our best moments in travel are the spontaneous trips, the abandoned days, the afternoon spent lounging on the beach in favour of seeing it all.
A day or two before our departure, we call or email restaurants to confirm our reservations. At this time, we also print everything, including boarding passes, hotel confirmations, tickets, restaurant reservation exchanges, google maps and other pertinent paperwork. This has saved us so many times! For instance, in Costa Rica earlier this month, a company scheduled our rainforest cloud walk for the wrong day. Austin pulled out the email confirmation and the situation was quickly remedied.
We keep copies of our passports, travel visas and our marriage certificate stowed safely away from our other travel documents (in case we need proof of marriage, because we hold different citizenships, and in the rare and horrible case we were to lose our passports abroad).
This process may seem like crazy over-planning* (that’s okay, I get it!) or it may be helpful to you. I think at least some portion of itinerary-building benefits all travelers, whether travel is something you do frequently or just a couple times a year. We love the physical act of travel and exploring new places, and a big part of that love is the preparations we make to ensure a happy, mostly-stress-free and adventure-filled trip, with room for spontaneity.
*EDITED TO ADD (2015/05/13): I recently received a somewhat inflammatory message about our intense (“OCD”) travel planning process. I understand! This isn’t for everyone. My husband and I are both planners to the core, and to us, planning is freedom. If you’d rather buy a plane ticket and just go, that’s an equally valuable way to experience the world. It would stress me out. Successful travel requires figuring out your preferences to make these finite vacation days as wonderful as possible.
Our master trip itinerary planner on Google Documents (make a copy and use it!).