planning a travel itinerary | a step-by-step guide

Travel Itinerary GuideRecently, 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!

the met rooftop new york cityPre-Planning

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.

Using Pinterest to Plan Traveltravel planning on pinterest

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!).

reykjavik iceland

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:

Technical Details

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.

High-Level Itinerary

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.

park guell barcelona

Local Details

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!).

nuit blanche paris

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).

san antonio texas

To Conclude

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!).

A sample google map for Paris, France.

My guide to our travel gear and minimalist packing.

8 thoughts on “planning a travel itinerary | a step-by-step guide

  1. maria,
    i really admire you ability to organize and plan. my main thing is i get information overload and so i get overwhelmed and nothing is retained. walking away and going back to it later is a great idea, one that i know makes sense but one that i rarely do.

    i am so looking fwd to reading about your travels this year!

  2. Lan — I get where you’re coming from. I have serious perfectionist tendencies, so always have to get over the hump of planning “the best trip” to just plan something. Austin has helped me with this… I’ll be researching 10 museums and weighing their relative merits, as he knows when to gently tell me to stop and just choose one.

  3. This is amazing!! Thank you so much for writing this. I used to very minimally last minute plan for trips (resulting in staying at a hostel in the Amsterdam red light district haha), and I’m slowly slowly adopting better habits. I’m bookmarking this to use for my next trip 🙂

    1. Thanks so much, Kathryn! I completely hear you and can relate. I spent many of my younger years as a fly-by-the-seat-of-my-pants traveler, which led to some uncomfortable/crazy situations to navigate in foreign places… the peace of mind is so worth building a little itinerary, even if you start small with the key details and build up over time. So glad I could help. 🙂

  4. I absolutely do not think you over plan things…perhaps because my boyfriend and I plan very similar to what you guys do. 🙂 Like you the thought of just showing up without a plan doesn’t sound like fun to us so we have a detailed plan for each day. Many people have seen our plans and think we’re too rigid but not true! If we like something more than we anticipated and want to stay longer, well we do. If something is disappointing and we have it scheduled for an hour, well we move on.

    My boyfriend also makes our Google maps to pin all the things we want to see, and then he enters all the addresses in the order we’d like to see things to avoid wasting time backtracking. He also enters all the addresses into his navigation program that we use on road trips (Nokia Here) and then all we do is click on the next destination and we’re off! No fiddling with finding the next address and entering it in. We’re actually getting quite proud of ourselves for the itineraries we’ve created as we’ve seen tons of stuff, without feeling overwhelmed.

    I agree with you too- this method isn’t for everyone and to each their own when planning their trips. As long as everyone has the experience they were hoping for when they travel that’s all that matters. 🙂

    Wishing you guys lots of wonderful travels!

    1. Stacey: Thank you so much for this thoughtful (and useful!) comment. I just visited your space and love your approach to planning travel — the concept that we can build adventure into our lives even if we have regular jobs that keep us in one place for much of the year. That’s very much the philosophy my husband and I take.

      I love your idea of pre-entering addresses!

      And I think you hit on a key point. The itinerary really is freedom. I don’t feel overwhelmed or over-scheduled — just that I’m making the most of my finite vacation days.

      Happy travels to you both! Glad to have a new like-minded travel read. 🙂

  5. I am in the process of planning a trip to Italy for my husband and I in March and I just LOVE this post! I have Pinterest boards, spread sheets, a TripIt planner and guidebooks. I know where we’re going when. I have confirmation numbers, addresses and contact info for everyone and everything and yes, it’s party crazy and obsessive, but when I land in Italy it’l be a comfort to know where I’m going, how to get there and that we’re (hopefully!) going to get to see and do everything we want to!

    Like you said, not for everyone, but I love my trip planning and itineraries!

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