How to Effortlessly Plan a Vacation | Flights

While we were away in Athens recently, I got dozens of messages each day with questions – not about the city itself, but about packing for it. A surprising number of people asked me to reveal what I wore and didn’t wear from my suitcase when we got home, which struck me as interesting. But I also knew it would be impossible. I have a system for packing, like I have a system for everything. Nothing I pack when I go on holiday goes unworn.

I really do have a system for everything. For me, life is a series of problems just waiting for me to find creative solutions to – and I love that. I love refining and simplifying, getting better and faster and more efficient in everything I do. Especially in things I love to do. And travelling is the thing I love most – or the second most, after shoes.

My first foray into travel planning was a twelfth-grade English project. We were assigned a research paper, and I wrote about a trip to London and Paris that Mom and I took the same year. It was still early days for online travel booking back then. What now takes two minutes to Google took hours of diligent searching, but it didn’t matter – I was hooked. I get as much joy from the process of planning a trip as I do from actually taking one. But I know there isn’t as much fun in it for everyone, especially if you don’t know where to start. So I’ve finally put together all of my best travel booking tips and tricks to help you simplify your holiday planning – and do it without breaking the bank, too!

This post is the first in my How to Effortlessly Plan a Vacation series. In the coming weeks, I’ll cover booking accommodations, itinerary planning, packing and more!

Before you start…

1: Know that flexibility is key – especially when you want to book an affordable holiday. Instead of choosing one destination, make a list of five or six places you’d like to spend your vacation. Once you’ve research flight prices, you’ll know which one to choose!
2: In keeping with the idea of being flexible, I recommend doing your research prior to requesting vacation dates at work or making any official bookings. Sometimes, travelling on a Wednesday versus a Friday means substantial savings – but if you already have set vacation dates, you can’t take advantage of that.
3: Set a vacation budget – and stick to it.

Flights

There are so many amazing tools out there to help you find the best price on a flight. But given that there are so many, it can be hard to know which ones to use – and even harder to see which ones might come with hidden costs. When booking our honeymoon, I learned the hard way that some agencies advertise incredibly low fares but make up the cost difference in the own fees, which puts you no further ahead. Since then, I’ve figured out the best resources to rely on for flight information – free of charge.

1: Start with Skyscanner

This site is an amazing resource for finding reasonable flight prices, especially if you live in a major city. Note: This is totally not sponsored. I rely on and trust Skyscanner deeply. Using a complex algorithm, it allows you to enter a variety of combinations of information, including your starting point, travel dates and/or destination – but also leave any of them blank – to find the best fares to or from vacation destinations worldwide.

I admit – Skyscanner has limits. It works much less well if you live in a small city, like, say, Winnipeg, from which very few direct flights to anywhere depart. In major cities, it practically works (travel-related) miracles. But I still use it here in Winnipeg because it allows me to input possible vacation dates and get a sense of the least expensive places to fly within the time period I want to travel. The result is that I often find myself considering destinations I would never have thought of otherwise. In fact, it’s exactly how we wound up going to Florence last year when we planned to visit Lisbon!

We use Skyscanner to help narrow down where we want to go from our list of possible destinations, based largely on price and convenience of flight times. After that, we move on to booking.

2: Avoid booking directly with an airline (if your budget is your priority)

That’s a controversial statement, I know – but trust me, I’ve done the math. Airlines don’t advertise offering the lowest price on fares on their flights because it’s rare that they offer it. Especially once you add in all the extra fees they now charge regardless of who you book with. I’m talking about luggage charges, seat booking fees, drink fees (and more…!) We’ve all signed inwardly and paid those fees at least once.

There are reasons to book directly with an airline, like if you want to be able to pay to book your seat in advance. Or if you areare looking to fly in a class other than economy. But if you’re travelling on a budget and want to save money to spend once you reach your vacation destination, there are definitely more affordable fares to be found through third-party booking agencies.

3: Find a booking agency you like – and stick with it.

We use Expedia. I’m sure some of you know that, because I’ve proudly worked with them before. But the fact is, I was a customer long before I worked as a brand partner. There are a number of things I liked about Expedia versus their competitors. Some are simple, like that their interface is bright and easy to navigate. Some are a bit superficial – Expedia offers points and it’s fun to see them add up. (And more fun to use them for discounts on future bookings!)

But most are practical. We invariably find the best flight prices from the most varied selection of airlines on Expedia. Since they are a third-party agency, they are able to combine flights from multiple airlines into one ticket. That means we have way more departure time and layover options than we would if we booked through a single airline. And sometimes, somehow, they come up with the most amazing deals. Seriously: this summer, we booked return flights to New York City through Expedia for $287 including taxes. Those flights include a stopover in Toronto, and the flights to Toronto alone on the same November dates cost twice as much!

If Expedia doesn’t work for you, I’m sure you’ll be able to find a third-party booking agency that will – there are dozens online. We’ve also used Hotwire in the past. We’re loyal to Expedia now because it combines affordability with the services that are important to us. And as an added bonus, there are no fees on top of the price you see on their site when you do your initial search on their site. What you see is what you get!

My Process

Choosing a destination and booking flights is the start of every holiday plan for me. And this is exactly how I do it…

1. Brainstorm five to six places I’d love to visit, as well as a month of the year when I’d like to go.
2. Research flight prices on Skyscanner to see if any of the destinations are affordable. This usually narrows my list down from five or six places to two or three. Sometimes, it means I have to go back to the drawing board entirely.
3. Cross-reference the most affordable destinations on my list with the most budget-friendly dates to fly to them. (When doing this, I usually also take a look at accommodation prices on those dates, to make sure I’m not picking an affordable time to fly that turns out to be a pricey time to stay. Note: I do this all by hand in a notebook. But since most normal people gave up analogue writing a decade ago, you’ll likely find it easier to track in an Excel spreadsheet. Keeping notes helps a lot, because prices posted online can change quickly.)
4. Settle on a final destination and the best dates.
5. Request vacation days from work.
6. Once the dates are approved, book my flights!

It sounds like work – but is actually so easy. And pretty fun, once you get into it.

Booking flights is something many of us now do frequently. But that doesn’t mean it’s an easy task. We all have a finite amount of vacation days each year, and in our fast-paced lives, where our decision-making is often driven by a fear of missing out, we feel constantly mounting pressure to make the most of them. That can make the act of actually planning a vacation stressful. And nothing about a vacation should be stressful.

While some of these tips may seem like a bit more work than your average flight book, I promise that in the long run, they’ll make your flight bookings so much more effortless. And that will save you time and energy to enjoy the most important part of your vacation – the trip itself!