And we’re off! — A Trip Planning Guide

February 2018: Soaking up the sun in Portobelo, Panama

So you want to sip a cocktail under the Caribbean sun on a beach in Barbados? Or maybe see the ancient Egyptian pyramids in person? How about a long weekend girls trip to Las Vegas? Bali, anyone? Regardless of where you’re headed, thinking of heading or daydreaming of visiting, this guide has you covered from point A (the idea!) to point Z (the execution!). 

I’m sharing the foolproof method I use when planning any of the trips I go on, no matter how big or small. If you want to live out your travel dreams but don’t know where to start, keep reading and this guide will have you organized and putting in your vacation requests at work in no time!

Step 1: The 5 W’s & 1 How of the trip

🎶It was all a dream, I used to … only see these places in travel magazines. 🎶
Hey, you gotta start somewhere right? Whenever a place pops in to my head or I start to get that travel itch, the first thing I do is answer these questions: where, what, why, when, who and how. 

Most of the time “where” is already decided, but not always. In cases where I need some inspiration I usually turn to my saved posts on Instagram. I have a “wanderlust” album that’s full of pictures of pretty places I come across when scrolling the ‘gram. Other sources of inspiration are Google Flights (you can leave the destination field empty and check out flight deals around the world), and a few websites namely, National Geographic, Lonely Planet and Condé Nast Traveler. 

Why I want to go and when I can go are the next things I clear up. The why can be as simple as a flight deal, having heard great things about a place or really wanting to have a lobster roll — which was the motivation behind my road trip to Maine last September. Who I want to go with (if anyone at all) and what the destination has to offer are especially important. The “who” can make a trip or break a trip, point finale. And “what” helps me decide if the trip is a wise choice given the weather, time I have, political climate, etc. 

Now we’ve reached the “how” and this part can be heartbreaking. How exactly am I getting there? For smaller local trips, there are options and its really just a matter of choosing something that is practical and budget-friendly. However, for international trips the pickings are slim and air travel is often the only option.
Here are 4 things I do to put the travel gods on my side:

  1. I always search for flights on incognito mode

  2. I started searching early

  3. I stick to my favourite reliable sites, like Google Flights, Skyscanner and Kayak

  4. I try to be as flexible as possible with my dates. If I have no specific date in mind, even better! I browse for the cheapest time to go.

This is also a good time to look into the overall budget for the trip, because transportation is only a fraction of the spending. Don’t forget you’ve got to eat, sleep and play on this trip as well. Everyone’s travel standards are different, but I think looking into how much accommodations would cost will give you a good idea of whether this trip is in your budget or not. My approach is to open Airbnb, put in the filters I know will apply and get a sense of pricing for places I can actually see myself staying in. There’s no point in including private rooms in this search if I know that isn’t my travel style. Don’t waste your time looking at hostel prices if you don’t see yourself ever staying at one. Another option is to check out the daily spending estimates provided by travel sites like Lonely Planet under “Money & Costs”, but again spending is highly variable and subjective to the traveller. 

Now is also a good time to skim some less interesting stuff (but super important nonetheless), like entry/exit requirements for the country, vaccines and any travel advisories that have been issued. 

Technically you could answer this question first to avoid disappointment, but I like going through all the steps so that the information is ready and accessible when I’m planning a future trip or when a couple of days off randomly fall into my lap. 

Step 2: The Big “travel” Picture

May 2018: At Pierre-Elliott Trudeau Airport waiting to board my flight to Montego Bay, Jamaica

Now that you’ve gotten the ok from work, your whys, hows and whats all align, whatever mode of transport has been booked… you're going on a trip fam!! Celebrate! This step is my absolute favourite part because it’s all about the broad outline of the trip which I breakdown into the 3 A’s: accommodations, attractions and accounting (which is not fun, but a necessary evil).

Making this list is a must for me because it ensures that I don’t forget anything and provides the building blocks of the final itinerary.

I usually start by getting a general idea of the major attractions the place has to offer and making a list of the things I absolutely want to do or see. My main resources are the official tourism websites, Rough Guides’ “Things not to miss” and sometimes TripAdvisors’ “Things To Do”. Making this list is a must for me because it ensures that I don’t forget anything and provides the building blocks of the final itinerary. I’ve gotten into the habit of buying a physical travel guide — either Lonely Planet or Rough Guides depending on which one has the most recent publication out, for bigger trips like the one to Morocco and Thailand. I recommend it. It’s helpful having something to take with you, seeing as wifi can be limited and spotty in some countries and both guides provide concise and relevant historical context to the places you visit. 

Accounting is essentially the budget of the trip. Of course even before booking the flight you got a sense of what to expect. But now that you’ve listed out the major things you’d like to do and you know how much it’s costing to get there, you can be more realistic about what you want to spend on accommodations. I ALWAYS do this before really looking into where I’m going to stay, because for me there is no heartbreak greater than falling in love with a place I know is so far outside of the budget that there’s no justifying it. Still, hunting for the perfect accommodation is my favourite part of the planning process. My go-to websites are AirBnb or when I have an extended stay because they have competitive prices and has a rewards program that allows you to collect nights. I use Tripadvisor’s forum, the proximity to the top attractions I plan to visit and my overall vision of the trip (e.g. spending quiet days on a beach or being in the centre of all the action) to help me decide which cities or neighbourhoods to look into staying in. 

February 2018: The courtyard of our 2-bedroom suite in Casco Viejo, Panama

Allow me to preface this by saying that not everyone is big on planning the finer details of a trip and the thought of an itinerary actually makes them nauseous. And that is totally ok.

Step 3: The Finer Details 

Now that accommodations are set and you know the major activities you’d like to do, it’s down to the nitty gritty. Allow me to preface this by saying that not everyone is big on planning the finer details of a trip and the thought of an itinerary actually makes them nauseous. And that is totally ok; you decide how deep into the nit and the grit of if you want to go. Plus, some trips call for much less planning than others. Personally, I’m so guilty of making nausea-inducing itineraries; in fact I’ve made one for all of my major trips and I have no regrets. Humour me for a moment and let me tell you why:

  1. I like that it keeps things organized — I have a good sense of what’s happening when 

  2. It ensures  that I make the most of my time away (and the money I spent on the flight to get me there!). Imagine paying $1000 to fly halfway across the globe with loose plans of seeing everything and anything only to realize on Saturday afternoon that “attraction x” is closed on Sundays and Mondays. Kinda sucks.

  3. It saves me money. Planning out what I’m doing when or where I plan to be allows for savings through early-bird tickets, shopping around for the best prices (e.g. with tour companies), and weekly specials at bars or restaurants.

  4. Remember, an itinerary can be as flexible as you want it to be. Nothing (other than maybe tours or flights you may book in advance) is set is stone. 

When it comes time to make an itinerary, I always start off with scheduling in the bigger attractions and activities, such as day trips. Then I fill in the rest, like low-key activities, nearby sights, free things to do, neighbourhoods I want to explore, cool local spots, restaurants, and shopping. This is the part that requires more digging and research. My favourite tools to use are the country’s official Instagram account, Instagram hashtags (so, so useful for finding fun local spots), recent blog posts, Tripadvisor and depending on the destination, the websites Thrillist or Culture Trip. 

Lastly, I map things out using Google Maps and save the locations I plan of visiting for easy offline use when I’m actually there.

October 2016: Day trip to Chefchaouen, Morocco

September 2017: Beer tasting in Portland, Maine


Planning a trip can be a daunting task, but I really believe breaking it into smaller little steps and being mindful of the type of travel experience you want makes it not just possible, but so worth it. I hope this guide fuels you to book that next trip, wherever it may be, and that you feel more equipped to take on the challenge. How far in advance you start planning really depends on your personality and the destination, but giving yourself 3 months would be a good middle ground. Remember to customize the steps to your travel style — make this guide yours!

Don’t forget to drop a comment and let me know how you plan your trips. Was this any help? Happy and safe travels :)

Stay kind & stay curious,


P.S. Keep an eye out for my next guide on how I prepare for a trip. I’ll be covering everything from packing to travel health! Be sure to subscribe to my mailing list if you haven’t already :)

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