The Ultimate Guide on How to Plan a Trip


Let’s face it. Planning a trip is both exhilarating and overwhelming. It’s exhilarating because you get to imagine yourself living it up abroad by exploring awesome destinations and taking a break from your daily life. It’s overwhelming because there are so many decisions to make and so much information to digest.

You also want to make booking a trip effortless, like putting on shoes. Yet, how many times have you had a zillion tabs open on your computer and feeling as though you will be going no where soon? It’s ok, we’ve all been there.

I believe all you need is a system or a series of steps to go by to plan a trip overseas. If you frequently get stressed with trip planning or maybe this is your first trip or big trip overseas, follow my suggestions bellow. Not only will you have a blast, but you will even enjoy the planning and booking process!

Research and Make Decisions

Oh, I have hit you with a big one right away. If you can’t nail this one down, then leave your suitcases in storage because you are going no where. It’s crucial to determine where, what, with who, when, and for how long your trip will be.

Location, Location, Location: I suggest starting by writing down where you want to go if you had all the time and money in the world. Then, look at the list of places and decide which places make you feel the most excited and is the most realistic with time and budget constraints. But, don’t forget to dream. Follow some new travel influencers such as those that I have recently written about and see where they have been and if you can go there too.

With that determined, start researching the specifics of the destination(s). Look at the city’s and/or country’s tourism site and social media (e.g. Instagram account) on their recommendations and highlights. If you are thinking about going to Scotland, I highly recommend checking out Visit Scotland.

Find out about:

  • Unique activities that are different or not available at home

  • Shows or concerts to attend

  • Best restaurants, bars, cafes

  • Shopping streets

  • If you need a visa and/or vaccinations

At the end of this stage, you should have a solid grasp on what is unique and worthwhile of each destination.

A bestie and I in Biarritz, France. Circa 2012.

A bestie and I in Biarritz, France. Circa 2012.

2. Solo or People: Once you have gotten a fairly good idea of the destination(s), start thinking about who could go with you or if you feel brave enough to go by yourself. I have enjoyed traveling both by myself and with friends.

When you travel with people, realize that you will spend a lot more time with them than you are used to. Make sure you talk about how to deal with issues ahead of time, check in with yourself that you feel comfortable traveling with them and that it will not ruin your relationship. At the same time, traveling with friends can also bring you all a lot closer.

When you travel by yourself, realize that you are the only person that can get yourself into and out of trouble. You are responsible for getting yourself around a new place, meeting people, and making everything happen. Ensure that you are comfortable with this before leaving. If done correctly, solo travel can be very personally transformative.

3. Tour or No Tour: It’s also a good idea to decide if your trip should be tour based or free-style, regardless if you are traveling solo or with others. My rule of thumb is the less familiar with the destination I am and the more complicated it gets to see as much as possible, the more likely I will take a tour.

4. Communication: Consider how you will communicate with people back home, your travel buddies, the local destination, etc… For long-term travel, I recommend getting an international SIM card in an unlocked smart phone. For short-term travel, I recommend locking your phone on airplane mode and using wifi, especially if you are from a country with the worst phone rates ever such as Canada.

Save all tour options, accommodations, activities, all transportation (flights, busses, trains, etc…), and travel insurance possibilities. You can bookmark this on your Internet browser or print it off.

Budget Time

Now things get really nerdy. Travel is so much fun, but it does get costly. Here is when you should note the costs of everything for your trip to happen in an Excel spreadsheet. Also importantly in this step, you should research discounts (student, tourist, early-bird, credit card points, etc…)


  • the cost per person and group rate (if applicable)

  • how much foreign currency you need and the conversion rates

  • dates

  • important information (e.g low or high season)

  • the total

Calculate a little breathing room in your budget for accidental cost over-runs because things happen! Also, ensure that your credit card won’t go over its limit.

Make sure you calculate everything into your home currency. It’s easy to ignore symbols and abbreviations next to numbers…

If you are planning a trip for some time in the future, know definitely how much money you need to save, what you need to put aside each pay cheque, and what spending habits need to end or be altered.

Take that lovely total and subtract it from your bank account. Are you still happy with the amount remaining? If not, make some adjustments. If everything is fine, proceed to the next step.

Book Everything

Photo by Raw Pixel, Unsplash.

Photo by Raw Pixel, Unsplash.

Get yourself a cup of your favourite hot beverage, your research, fully charged laptop, uninterrupted time and book the trip. Booking a trip is like ripping off a band-aid — you feel super antsy at the start. Once it’s all done, you feel so accomplished and relieved! Plus excited!!

The most time consuming components of this stage is booking your flights and accommodations. Here are my tips to breeze past this step.


  1. Join the email list of major airlines, giving you advanced notice of sales.

  2. Be flexible with your dates and booking in advance always helps to save money.

  3. Search for your flights and book them in private browsing, as it doesn’t allow the sites to increase the price a little every time you return.

  4. I recommend using sites that compare different flights for you such as KayakSkyscanner, and Expedia.


Photo by To a Heftiba, unsplash.

Photo by To a Heftiba, unsplash.

Based on who you are going with (friends, significant other, family) or even by yourself, this will determine the style of accommodations you need for your trip. Consider the following:

  1. How much privacy do you want?

  2. How comfy do you want to be?

  3. Do you need quiet time/space to relax at the end of a day?

  4. Do you want to cook most or all your meals?

  5. Do you want access to your own laundry facilities?

  6. How important is good wifi to you?

  7. Where in the city/town do you want to be?

Hostels, although great on your wallet and for meeting people, but won’t be very privacy or cooking-friendly. AirBnB on the other hand, will offer lots of privacy, a fully stocked kitchen, great wifi, but more separation from people.

Once you are done, double check all the dates for your entire trip. Write it down on your calendar and review each day systematically, because you could accidentally forget to book accommodations for a night. Of course I have not done that…

Travel Insurance

The most underrated and annoying thing to buy is travel insurance. You hate to think about it, but you are sure glad to have it when you need it. I recommend getting travel medical insurance at the very least. You can also get baggage, cancellation and interruption insurance. Whatever your budget, you must get it. As travel blogger Y Travel puts it, “If you can’t afford to buy travel insurance, then you can’t afford to travel”.

According to Manual Life, travel insurance protects you from the unexpected while abroad, from the minor inconvenience to serious situations. While every policy is different, you want to pay special attention to the following:

  • What coverage is omitted due to destination (due to a travel advisory), activities (high-risk), current medical condition, acts of God, and replacing valuable electronics?

  • How do you submit a claim and get reimbursed?

  • Know the size of your deductible, which according to Medipac Travel Insurance means the amount you are expected to pay in the event of a claim.

  • Are there upgrades and premiums you should be aware of? (e.g. cost of insuring baggage)

  • Especially for a long trip (but applicable to all travel time), know which countries you are covered for and for how long. Based on my own experience, adding the U.S. to your trip increases the cost of insurance.

  • For women, check if an unexpected pregnancy is covered by your policy.

Source: Y Travel Blog

Leading up to the Trip

Photo by Erwan Hesry, unsplash

Photo by Erwan Hesry, unsplash


Regardless if you are a last-minute packer or packed weeks before (I am the former), you need to review your luggage. This is important for several reasons:

  • Choose hassle-free and durable bags. It sounds evident, but choose bags that zip and move easy, especially your carry-on.

  • Make a list for everything you want to bring and really visualize yourself lugging all your stuff from place to place, climbing stairs, etc.. If this already makes you sweat, consider trimming that list.

  • Put some thought into your carry-on, as it could be a life-saver if your checked luggage gets lost or delayed. I recommend putting at least one to two days worth of clothes and various 100ml toiletries in a clear pouch, and have enough things to keep you entertained and comfy on the plane. For instance, I always get terrible nasal congestion on planes and I am a germaphobe. So, several packs of tissues and hand sanitizer are a must bring for me!

  • Decide what tech (laptop, camera, SD cards, tablet, etc…) you want to bring.

  • Make sure you bring the right adapters.

  • Know what clothes to bring beyond the weather, i.e. the appropriateness for conservative countries and events.


In addition to luggage, there are also miscellaneous, yet important things to think about and research.

  • Make sure all your documents are in order such as passport is not expired/will expire, print out important confirmations, back ups saved on smart phone, and make copies of travel insurance policy and calling card.

  • Have a system in place in case you get sick, especially in a developing country

  • Know some basic phrases and key words in the language of the destination(s)

  • Ladies especially, know what to do and say to keep yourself and friends safe. I don’t mean to get paranoid, but have your basics covered. For a comprehensive list, check out this article by She is Not Lost.

  • Check your country’s travel advisory site for the latest warnings and information on your destination(s). Canadians, check out the Federal Government’s travel advice and advisories.

  • Do a hop-on-hop-off tour in each major city so that you can get the lay of the land without having to move too much. It’s perfect when you are jet lagged but feel guilty staying in.

  • Download the app city mapper that helps you get around several major cities around the world. I used it while in London and it was a life-saver!

Photo by Becca Tapert, Unsplash

Photo by Becca Tapert, Unsplash

Enjoy Everything to the Max

The most important thing to enjoy while abroad is to revel in the feeling of being free, discover new places and meet new people. You don’t need to check off everything that there is to see, nor do you have to perfectly plan everyday, unless that’s your thing.

Sometimes things will go wrong that are beyond your control. Learn to roll with it, treat it as a life lesson.

Sleep in some days and get up ridiculously early to see the sun rise another day.

Talk to someone that thinks differently from you and someone compatible.

Eat healthy and try all the varieties of chicken tagine (or some other local staple) that you can find.

Drink wine underneath the roof deck of your accommodation and watch the rain pour down on a different view. Bonus marks if you watch a thunder and lightning storm!

There’s nothing else to consider now except to go and enjoy your trip. Every time you go abroad is different from the last and deepens your knowledge of this crazy and amazing world we live in.