Booking Hotels: Maximizing Points & Making Sure You're in the Right Spot, for the Right Price

Bri and I have been on the move for decades now (which is wild to think about, quite frankly), and I’d like to think we’ve picked up a trick or two along the way when it comes to booking hotels and maximizing travel points. I’m going to work through some of my favourite strategies to enable you to travel better, cheaper, and smarter in your coming adventures.

The Chelsea Hotel in Downtown Toronto — Staying at the Chelsea Hotel in Toronto, Canada. Photo Credit: Christopher Mitchell

You’d like to think, after 20+ years of my life dedicated to travel, living abroad in no less than 4 nations in that time, and visiting nearly 100, that I’ve picked up a travel hack or two along the way. In truth, if I hadn’t, that would be borderline concerning.

I’ve never been the writer or content creator to pretend to have all the answers, but I do feel as if, at the very least, I try to ask the right questions. In truth, I’m actually rather taken aback by the amount of people who will advertise on social media that they have all the answers (whether that be in blogging, becoming an influencer and landing brand deals etc.), and they’ll share them with you via a course for x amount of dollars.

Generally speaking, if you can’t clearly understand how someone makes a living, and you buy their course, you’re probably the way they make a living. I’ve always loved that quote from André Gide, “trust those who seek the truth but doubt those who say they have found it.”

All that aside, and before I veer off into the world of the philosophical, at travelingmitch, the goal for Bri and I has always been to share honestly, from experience, and to help our readers on their path, as best as we can. We just spent a month in Europe, and the bulk of our flights and hotel were covered by points and so forth, largely because we’d tried to become increasingly travel savvy over the years. Why not, right?

It only felt right to take a moment to share a touch of what we’ve learned, so I thought I’d take a moment to do just that.

What 20+ Years of Travel Has Taught Me About Booking Hotels & Flights (and Maximizing Points

Search (and Book) Incognito

I’m not your prototypical tinfoil hat wearing conspiracist, I promise, but if you don’t think your Search activity is being tracked in some regard, you’re probably not living in reality.

We just spent some time in Turkey / Turkiye, and flew with Turkish Airlines a number of times, and now my entire Facebook feed is ads from Turkish Airlines. Coincidence, I think not.

Innumerable times in the past, Bri or I would be searching for hotels, would not be searching incognito and then magically the price would go up if we performed another search that day.

The solution is simple, search for your hotels or travel arrangements with an incognito browser. With Chrome, for example, it’s as simple as going to “File” then “New Incognito Window.” If your passwords are saved on your browser, you should still be able to use them just as easily in Incognito mode.

Something small to do, but not insignificant.

Use AwardWallet

If you’re looking for one place to track all of your travel plans, your loyalty points for respective hotels and airlines, as well as your credit card points, it’s AwardWallet. It can be a little annoying and finicky to set up at first, since not all programs are integrated with it, but it’s a very helpful tool to see the total value of your hotel and airlines points, and perhaps more importantly, to see when they expire.

I appreciate that when I’m taking off, I have one place to see all my confirmation numbers, get live updates about gate changes, and then when I land, I have the address of the hotel and confirmation there.

Personally, I felt as if I needed a “headquarters” of sorts to keep track of everything, and that’s when I found AwardWallet, which tracks nearly 650 loyalty programs.

Subscribe to Some Crafty Travel Newsletters (and communities)

I offer a lot of travel tips, tricks, and advice on my newsletter, as well as weekly advice for creators over at This Week in Blogging, but my advice isn’t geared as much to timely deals as it is to timeless advice (at least that’s the goal, particularly with the travelingmitch newsletter).

There are a few newsletters and communities that I like:

Daily Drop: Learning to maximize points in under 5 minutes a day. He’s quite personable and crafty, and it helps you think outside the box when it comes to travel rewards.
Prince of Travel: This is a bit more focused on maximizing points and travel rewards for those from Canada, but it’s a well researched newsletter and website.
Going: This was formerly known as “Scott’s Cheap Flights,” and in many ways Scott was the original when it came to publicizing travel deals en masse. Going has switched to a paid model, but if you’re travelling a lot you may find some value there, and I do know they offer free trials as well.
Dollar Flight Club: Another newsletter I like even just for ideas about where to go next. I’ve seen some great deals here, and you can join, add your home airport, and then the rest is taken care of for you.

I’d also recommend joining the newsletters of the hotel groups that you frequent most. Hilton, IHG, and all the rest regularly have flash sales. The same is true for airlines, by the way. I’ve gotten some great deals just by being informed that way.

Lastly, look on Facebook for local groups that specialize in deals for your airport. I’m follow the “YYZ Deals - Toronto Flight Deals & Travel Specials” page for example. You may want to be a part of larger, general groups as well such as “Flight Deals” and “The Flight Deal Group.” Do a little hunting, join a few groups and pages, and then see what serves you well.

I feel as if the next frontier of flight deals may actually be headquartered in Whats App communities, so keep your eye out for that trend as well.

It’s All About the Credit Cards

First things first, with credit cards, you do need to make sure you’re in a position to pay off your credit cards and, in some cases, meet the minimum spend. Most big time travel cards have some sort of minimum spend to be eligible for the points bonus (for example, you might need to spend 3-6k in the first three months or something of that nature).

I’m going to talk about my collection of cards, but before I do, I want to mention that, as a Canadian, I’m more limited in my options. Most Canadian travel credit cards, it should be noted, still charge a 2.5% fee on any foreign currency transactions. That’s not a common problem in the US. I’ve talked to many of my travel savvy American pals, and the undisputed favourite is the Chase Sapphire Reserve Credit Card.

Almost all credit cards now are connected to a particular booking engine. My TD Visa Infinite Credit Card is connected to Expedia, and I often book travel through the “Expedia for TD” portal to receive up to 9x the points. However, on the ground, I use my RBC Avion Visa Credit Card, as I do not incur the 2.5% fee (originally I had the HSBC card, but HSBC was bought out by RBC here in Canada, and they maintained the no foreign transaction fee).

The crown jewel of Canadian travel credit cards, and travel credit cards in general (this card will likely be offered in some format wherever you live), is the AMEX Platinum Card. We’re talking a significant travel credit, big time points, a competent booking engine with excellent customer service, line bypass at Pearson Airport, gold status with Marriott, Hilton, and Radisson, status with many car rental companies, and a whole lot more. It comes with an expensive yearly fee, but if you’re travelling a lot, it’s very worth it, especially because it comes with Priority Pass, so you’ll have access to lounges.

Generally speaking, there’s no reason that you shouldn’t be booking through your credit cards internal booking system, especially if they have a deal. Plus, you can use those points you’ve saved up.

I should also mention that you should be mindful of currencies. I’ll use my RBC card in countries where the currency is a little weaker (our relatively recent trip to Argentina, for example), but I wouldn’t use that card in the US, where the currency is currently quite strong. Instead, I’d use my Wise Card. I have US clients send me USD there, and then I can use that USD to buy other currency to be used on one single card. That’s precisely what I did on our recent trip to Europe! It’s worth understanding, historically speaking, how respective currencies are performing.

Download All the Hotel Apps

I know what you’re thinking - “Look, I don’t need more apps on my phone,” but apps for the major hotel suppliers have come a long way.

I use hotel apps (Bonvoy, Hilton Honours, World of Hyatt, Best Western, Radisson Hotels, All) for a number of things:

Keeping track of timely deals
Booking through the app as an easy way to book a hotel and use my points
Downloading a digital key when I’m staying somewhere so, sometimes, I don’t even have to go to the front desk — and can get early check-in!
Understanding the privileges I have based on my status (water on arrival, late checkout, free breakfast etc.)
Adding the hotel reservation to my “Wallet” on my phone, so I have easy access to the key information, including the address of the hotel.
Reaching customer service if there’s anything wrong. I actually was able to, simply through the app, get a significant amount of points refunded, since there was an issue at the property that wasn’t communicated.

I’d recommend doing the same for airlines. I’ve downloaded all the apps to make it easier to check-in, track flight details, download boarding passes and more. These are also good places to check your available points, past stays, and upcoming stays, but do remember that you can indeed do all of that through AwardWallet.

Before You Book, cross reference with a search Engine

Before you finally hit the booking button on a hotel or credit card’s website interface, do a quick check on Google, Safari or whatever other search engine that you use.

You want to read reviews that are off the platform itself, where they can use rating scales that often are used to encourage you to book. On Expedia for TD, it might suggest it’s the perfect property, but perhaps the rating that I see on Booking or another travel amalgamator will tell a different story.

It never hurts to put in that extra moment, even when you’re on the final confirmation page (where you’ll often have up to 10-15 minutes to confirm) just to ensure you’re all set.

Check Out Room Cougar

Room Cougar is great for those who love video as part of the booking process!

Room Cougar is neat because they function quite differently than the traditional travel booking engine in that you can “look before you book.”

Their goal is to create videos of every hotel room around the globe, giving travellers a real, detailed look, in contrast to the way in which we can often see highly edited, wide angle views of hotel rooms elsewhere.

What’s also cool is that, if you end up excited about Room Cougar, you too can submit videos. They are offering $50 per video that is about 1-3 minutes long. Just make sure to capture all the highlights of the room and the view!

I also appreciate that they have discussion forums for each hotel room where users can chat about the pros and cons, so you can really get to the heart of whether it’s the right spot for you.

Your Next Trip Awaits, My Friend

That next trip is right there waiting for you.

This article was all about helping you to see more of this world of ours. The world of travel, in some ways, reminds me of the world of investing, where it’s all about access to information. There are always ways that we can put in extra work to save extra money, or to get onto platforms, like AwardWallet, where we can better understand how we can make our money work for us (again, not unlike investing).

When you can understand how paying a credit card fee that looks enormous (the AMEX Platinum currently being around $799) can actually save you money, then things start to get interesting.

In the end, it’s all about using information to make your travel journey not only less expensive, but also inherently better, and if I’ve done that for you in any small part, then that’s all I can ask. Onwards and upwards, dear reader.