Booking Travel the Smart Way!

June 6, 2018

I’m often asked how I manage to travel so often. My answer has always been the same: flexibility and getting what you want. On the one hand you need to be flexible in some areas of travel planning such as when and where you’re going. On the other hand, you need to have a set of principles you’re looking for in your travel experience. There’s no point booking a cheap flight if it means having an extra long layover in airport.  Every person has their own list of what constitutes what’s an acceptable hotel, flight, etc. The key is to have those principles at hand when researching your options. 


Today’s article examines in detail the two biggest factors of travel planning: transportation and lodging. 




One of the biggest misconceptions people have about travel is that travel is often done by plane flying from point A to point B. However, that’s not always the fastest, cheapest or most desirable option. For that reason I’ll discuss the three main ways people get from point A to point B when travelling: planes, trains and automobiles.




Flights are a common method of travel, especially when the distances are long (i.e. over 200 miles), cross a body of water (i.e. Atlantic Ocean), or are difficult to get to otherwise (i.e. Anchorage). It’s also the most stressful type of transportation. You’re constantly worried about prices going up and once you’ve booked the flight there’s all the planning that goes along with it: 

  • Will my bag fit in the overhead bin? 

  • What fees do I need to worry myself about?

  • How early do I need to get to the airport to clear security? 

  • What if my flight gets delayed or cancelled?


The first step in booking a flight is researching your flight options is using a flight search engine. While many people naturally gravitate towards the travel agencies like Expedia or Orbitz, I’d recommend starting out with Google Flights first. What’s great about the tool is at allows you to explore out a whole bunch of options quickly without having waiting a minute each time you search as on Expedia. 


Let’s suppose I live in London and want to travel to Houston to visit my relative in August. An initial search on Google Flights shows what the prices look like on flights:



Even though I’m booking travel a couple months out the roundtrip prices are ridculous. Fortunately, Google Flights suggests that there may be cheaper flights available if I’m flexible on dates. Let’s see what options are available throughout the month using Google by clicking on the See More link on the Dates group inside the Flights Insight section:



As you can see I can save about 60 pounds if I leave London on the follow day and return from Houston 2 days later - not a big change in my travel schedule. However it’s still not a major savings on my travel bill. The next step is to expand the search to nearby airports - Google can suggest nearby airports to consider by simply clicking on the Origin/Destination search box, clicking the plus button on the right then clicking See More Nearby Airports:



I’ll add in Manchester as another city I can take off from and Dallas Fort Worth and Austin destinations in addition to Houston. Let’s see if the prices change:



Choosing these extra airports seems to have dropped the price a little on the days I wanted. However, Google noticed that there are even cheaper fares available if I keep my schedule open, let’s see what they are:



If I take off on August 9th and return on the 21st I’ll save over 200 pounds on the fare. Not bad! Selecting the fare, reveals a potential issue…



The cheaper fares are from Wow Air and Norwegian, where you’ll often have to pay extra for everything from checked bags to meals (and often have long layovers in out of the way airports). Playing around with the dates on Google Flights, I find this fare:



It looks like Singapore Airlines operates a flight between Manchester, UK and Houston, Texas. While a bit out of the way from where I am (2 hours, 30 minutes by train), it’s non-stop service on one of the best airlines in the world, meaning I won’t have to worry about being nickled and dimed for things like checked bags.


Google Flights does an amazing job at highlighting the cost of fares across dates and locations. However, when it comes to booking the ticket, it may be possible to find an even cheaper fare using a service like Momondo which searches all the major travel agencies and presents the lowest possible fare. Plugging the dates into Momondo I get the following fare:



Looks like booking it through a third party agency will save even more money bringing the cost of the flight down to 353 pounds!


While this flight search turned out to be a resounding success, there will often be times where you won’t be able to find a cheap flight on any carrier, especially if you need to book travel at the last minute. What’s a traveller to do?! Enter frequent flyer programs like Air Canada's Aeroplan. These programs allow you to book free (or most often low cost), travel on their airline and partner airlines (a discussion on Airline Alliances can be found here). The best part? You don’t need to fly much to rack up frequent flyer points! Many credit cards offer the savvy traveller frequent flyer points for every dollar they spend on their card. Some popular cards include American Express Gold Card, United MileagePlus Explorer Card and the Chase Sapphire Reserve. Many of these cards award tens of thousands of miles, often enough to cover a domestic roundtrip trip. Another benefit to these travel cards is they often include travel benefits like access to business lounges and travel insurance.


To illustrate the value of frequent flyer miles, let’s suppose I live in Detroit and need to visit a family member who became critically ill in San Francisco tomorrow (I did this search on May 31st). Checking Google flights I see the cheapest flight is $708 CAD on Frontier (with a nasty 5 hour layover to boot!) :




However, using my Aeroplan points it costs 25,000 miles + $14.60 CAD:


A common misconception travellers have about airfare is that they need to book far in advanced (i.e. months in advance) to get the best deal. However, these days airfares are dynamically priced based on supply and demand. Purchase an airfare too far out and you may very well be committing to a higher price than if you booked closer to departure. Studies have shown that the cheapest price for a domestic flight can be found around 4 to 6 weeks out with international flights being booked out 6 to 8 weeks in advance. I would recommend checking flight prices every couple of days spending no more than a couple minutes. Google Flights also allows you to track the prices of selected flights which may also be helpful.


The price of an airfare is the first thing most travellers look at when deciding which flight to book. However, there are other considerations that should be considered which I’ll discuss briefly. 



It’s becoming quite common for flights to involve a connection in an airport or two. Many travellers forget to take into account the time it’ll take to go from where they arrival gate to their next departure gate. Sometimes you have to clear immigration, recheck your bags or go through security again. Don’t forget, flights can get delayed so your 50 minute layover can easily turn into a 20 minute layover. I’d recommend researching the airports you’re connecting to before you book that flight to determine how much time you should allow yourself to make the connection safely.


Another practice I see savvy travellers attempt are multi itinerary flights which can sometimes be a recipe for disaster. These are flights that are booked separately to get the absolute cheapest flight. For instance, suppose you want to go from Chicago to Tokyo. The cheapest method might be purchasing two sets of flights: one on Southwest that takes you from Chicago to San Francisco, and another on United which takes you from San Francisco to Tokyo. However, if your flight from Chicago to San Francisco gets delayed (or worse cancelled) and you miss your connecting flight to Tokyo, you’ll be at the mercy of the airline (United), who will likely just cancel the whole ticket on you with no refund. Talk about a bad start to a vacation! Hence, you should try and keep all of your flights under one booking, only then can you be protected if your travel plans go sideways!


The final hazard I should point out about air travel are that most flight tickets purchased today are non-refundable with some exceptions. That means that if you book a flight and your plans change you get your money back. Airlines will often issue you a credit you can use for future travel with that airline, usually valid for up to 12 months after you booked your flight. While that sounds good on paper keep in mind that when you try to use that credit the airline will assess a change fee of anywhere from $75 to hundreds of dollars, thereby reducing or even negating the benefit of the flight credit. Therefore it’s important to be 100% certain about your travel plans before you make that flight booking! There are two exceptions to this rule. Certain government regulations, like the US Department of Transportation’s rules on cancellations, allows travellers to cancel their flights within 24 hours of booking for a full refund. However, these flights typically have to be booked a week in advanced to qualify. The other major exception is international travel where you can often pay a fee of several hundred dollars to receive the refund. My recommendation is to read the fine print on the flight you purchase to review the terms for cancellation and changes.  




Train travel has several benefits over air travel. There's no security line up so there’s no need to be at the train station hours ahead of schedule. This also means you can bring on whatever food and beverages you want from outside without the fear of TSA confiscating it! Another way you save time is by having to skip taking the cab to and from the airport (easily saving another hour). Most train stations are located in the downtown core of major cities, meaning it’s a short walk not a taxi ride. Train travel tends to be more reliable than air travel - you’re less likely to face a cancellation and the delays on trains are often minimal. Comfort is another thing you’ll get in spades with trains - it’s rare to have more than a neighbour sitting beside you on a train, yet on many trains it’s common to get the dreaded middle seat. There’s also no turbulence and if you’re scared of flying, trains are the logical alternative!




Most importantly, the cost of a train fare can often be less than that of a plane fare. Don’t believe me? Here’s the cheapest roundtrip for a given day in June:



Here’s the price riding the rails:




Less than half the price and about the same amount of time when you factor in the time you’ll waste between airport security and taxi rides! Rail travel can often be the cheaper and more convenient alternative to air travel. 


Here are some popular rail companies by country:

…and Automobiles


Car rentals and/or Uber/taxis can be a efficient and cost effective form of transportation when travelling in groups (since you only pay one fee instead of train/bus fares for each passenger) or are  travelling to a destination that has you veer off the well beaten path. When I was travelling in South Africa last year, I wanted to see the Cradle of Humankind, a Unesco world heritage site which features caves dating back to the dawn of civilization. Unfortunately the destination was some 60 kilometres away from Johannesburg, where I was staying. Public transport options to there were non-existant and while I could have signed up for a tour group, I did not want to be forced to follow a strict schedule. Uber and taxis were also considered, although the concern there was the cost of the cab ride along with uncertainty as to whether the cab would be able to pick me up from this remote area.




In the end I determined that renting a car made the most sense. Here’s some tips I’ve collected over my years of renting cars globally:

  1. Your auto club or professional organization may offer discounts at many of the rental agencies of as much as 25%!

  2. Inspect the car carefully before you drive away and dropping it off, ideally taking detailed photos

  3. Avoid the in-car GPS and opt for Google Maps on your phone, it’s often more accurate and cheaper

  4. Familiarize yourself with driving rules and customs to the destination you’re travelling to

  5. Many credit cards provide rental car insurance so you may be able to avoid purchasing that expensive option at the agency

  6. Be flexible where you pick up and drop off your rental car - it can be much cheaper to pick up the car in the city than at the airport!


Last but certainly not least, you need to feel comfortable where you’re driving. Rental cars are not for everyone, especially when they’re in a far away land and are worried they’ll struggle to navigate uncharted waters. There’s no shame in admitting defeat and finding other transportation methods (i.e. tour group).




Hotels, hostels and AirBnbs are the most common ways people stay when travelling (in addition to the tried and tested method of crashing with friends and family). The main factors that impact the cost of accommodations are location and when you’re staying. Staying in a prime location like downtown will almost always be more expensive than staying on the outskirts of the city or a nearby city. A great example of this is San Franciscowith hotel prices averaging $400 per night! However, if you stay in nearby cities like Oakland or Redwood City that price falls by more than half! At the same time the laws of supply and demand play a huge role in the price of lodging. Staying during a major conference like CES in Las Vegas or during the summer months in Europe where travel is at a peak? Don’t be surprised if you have to open your wallet further! 


Regardless of when you travel you’ll want to make sure you get the best value for your money. Here are some things I consider when booking any lodging. The most important factor in choosing any lodging option (besides price and distance from where you need to be) are the reviews. Ideally I’d like to see great reviews like 4 stars on TripAdvisor with hundreds of reviews. Once I’ve highlighted those couple of candidate hotels I’ll dig into each of them and determine what’s included in the room rate. Hotels offer a variety of perks including free breakfast and wifi or lounge access for elites. I’ll also be looking for the hidden fees many hotels bury in the fine print like resort fees or parking fees. Finally, the check in and check out times for the hotel will let me know which hotels best align with my travel needs. For instance, if I’m arriving early morning into a city off a red eye international flight, I’d like to know that I can check in early and take a short sleep/nap. 


Lets now turn our attention to the types of accommodation available today, weighing the pros and cons and developing a strategy to book these stays.






Popular primarily Europe, hostels have become an increasingly popular budget option in expensive cities like New York and San Francisco, providing shared accommodations at a low cost (i.e. typically 20-40 Euros/night). Typically you share a room with several strangers, sleeping in bunk beds and sharing common facilities like the washroom and shower. It’s a great way to meet new people from around the world since you’re living in a communal environment. On the other hand, lack of privacy and security make many people stay away from them. Also, some of the things we travellers take for granted in a chain hotel such as having a 24 hour lobby allowing for late night check ins may not be present.






Hotels remain a popular lodging choice when travelling and the reason is obvious: consistency. The draw to hotels is obvious: stay at a decent hotel and you’ll have a clean, quiet and most important private room with your own bathroom. You know you’ll generally have a front desk and there may often be perks associated with the stay like free breakfast or earning hotel points. When you stay at a chain hotel like Marriott or IHG you’ll know that you’ll get a level of service and quality regardless of where in the world you’re staying. On the other hand, hotels can often be more costly than a hostel or an AirBnB. Quality can also be a concern at hotels, even those that belong to a chain. What’s a traveller to do?


Pricing is often the biggest challenge to finding a hotel. It’s easy to find a cheap poor quality hotel, but the decent hotels can be elusive especially in larger markets like New York or San Francisco. Just like flight bookings, you’ll need to do your homework. There are several factors which influence the price of a hotel: location, when you’re travelling, reviews and the hotel’s brand. For instance, you’ll be hard pressed to find a Ritz Carlton anywhere in the world that costs less than $500/night since Ritz is associated as a top tier hotel brand that offers personalized service. However, the other factors are within your control. If you travel to a city during a major event/conference or during its high season, don’t be surprised if the hotel options are limited and expensive! 


Let’s suppose I’m travelling to San Francisco for a week in August to visit friends. A quick search on Google lists the following options:




The cheapest decent quality hotel I could find was the Mosser Hotel for $227 CAD. Generally when I travel I aim to stay at hotels around $100 CAD regardless of the market, especially if I’m booking months in advance. Let’s look at hotels near San Francisco like Redwood City:




The lowest cost option is the Euro Hotel for $87 USD (~ $112 CAD). The hotel is close to the Redwood City Caltrain station which Google Maps tells me will get me to San Francisco in about 45 minutes. Now that I’ve got a candidate hotel, I’ll want to check the reviews to see what other travellers think of this place. TripAdvisor is my go to resource for this:


Looking at the overall rating and reviews, it appears that this hotel is legit. The last part to the booking process is finding the lowest price for the hotel. While Google is a great tool for getting a sense of the relative hotel prices, it doesn’t always list the lowest possible price. Here’s what booking aggregators like Trivago come in:



In this case the results displayed by Google were the cheapest!  


Sometimes the cheapest option is booking direct with the hotel, particularly if you belong to an organization that offers chain wide discounts (i.e. AAA). For instance, if I wanted to stay at the Westin Vancouver for a week in August the going rate is around $547 CAD/night:




However, when I visit the hotel’s website and indicate I’m a CAA member, the price drops:


This is on top of all the benefits I get from booking direct with the hotel such as free cancellation, the ability to collect and use reward points and my status with the hotel being recognized to offer such perks as late check outs, upgrades and complimentary breakfast.


A final way to offset the costs of hotels is to collect and use hotel points from the various hotel chains (i.e. Marriott). Those points are earned not only by staying at hotels, but also through hotel chain branded credit cards like the SPG American Express card, which also offers a bonus of thousands of hotel points. Sometimes it may even make sense to purchase hotel points and redeem them for a stay, especially when the prices for hotels are insane. 




A final option that is becoming increasingly popular over the years has been the emergence of the bed and breakfast and vacation rental booking sites likes AirBnb and Vrbo. Under this scheme travellers stay at someone’s house or vacation property for a fixed number of days (like a hotel). This has several benefits: they’re less costly than a hotel and you often get the expert guidance of a local. They can offer a similar level of privacy and cleanliness of a hotel if researched well. Since you’re staying at a home rather than a hotel, you may even have access to the comforts of home like a washer/dryer or full bathroom. A potential downside to these rentals is that you’re bound by the rules of the host who may limit the times you can check in/out or have house rules that may be too onerous on you (i.e. feed the cat). Coordination is often required between the guest and the host (i.e. to arrange key pick up or drop off) which is something you don’t generally have to worry about with the other options.


Here are the things I look for in an AirBnb rental:





We’ve discussed in great detail the various methods you can think about the travel you’re trying to book. While hotels and air travel are by far the most common option people think about when arranging travel, other options are available that may be more convenient and provider better value. Our next travel discussion will focus on the most likely reason you’re travelling in the first place: taking part in activities!

Share on Facebook
Share on Twitter
Please reload

Featured Posts

Surveys Gone Good

May 29, 2018

Please reload

Recent Posts
Please reload

Please reload

Search By Tags

I'm busy working on my blog posts. Watch this space!

Please reload

Follow Us
  • Facebook Basic Square
  • Twitter Basic Square
  • Google+ Basic Square

Follow me

© 2019 James Simpson



  • LinkedIn
  • Twitter