Good morning and Happy New Year from Ottawa International Airport, the best airport in the entire Ottawa metro area.
First, thank you all for your overwhelming response to last week's newsletter; we were thrilled to see so many thousands of you fill out our community survey (if you haven't filled it out, it's not too late).
As a reminder, The Daily Drop is hiring and we'd love to have you join the team. Check out our 100th newsletter from last week if you want to learn more.
Let's kick off the year with some good news, some strange news, and some EPIC travel strategies for the upcoming year 👇
- 💰 Southwest offers to reimburse passengers for travel expenses
- 🌎 Quick-hit travel stories to keep you distracted
- ✈️ My top travel hacking strategies for 2023
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💰 Southwest offers to reimburse passengers for travel expenses
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Remember that time that Southwest ruined Christmas?
Okay, that's a little harsh... But in fairness, they did cancel 15,000 flights and left people stranded without many options...
It seems they are seeking forgiveness because they recently announced a program to make people whole again through flight changes, refunds, and even reimbursement for certain expenses incurred during their meltdown.
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If your travel (through January 2nd) was delayed or canceled by Southwest, you can do the following:
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Rebook your flight for no additional fee (same origin and destination, within 30 days of original travel date)
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Request a full refund for your original booking
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Request reimbursement for reasonable expenses incurred as a result of Southwest's naughty behavior
So... basically, they're doing the bare minimum. Which I guess is better than nothing.
Although as a budget airline, I can't imagine Southwest suddenly changing their tune and not cheaping out.
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What remains unknown is what qualifies as a "reasonable" expense...
If your flight was canceled and you rebooked a flight on another airline for 5x the cost to make it to Christmas, is that reasonable...? I think it is, but I doubt they'd shell out for it.
This is all the language they have regarding which expenses are eligible:
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I suggest you submit as many receipts as you can. Maybe, just maybe, they'll reimburse you for everything.
Seeing how Southwest is under immense pressure from both the U.S. government and the court of public opinion, I'm hoping they'll set the bar pretty low for expenses they'll reimburse.
To submit a request, get a refund, or rebook your flight, simply go to this page on their website.
As a backup, I would also look into the insurance policy for the credit card you used to purchase the ticket. Many cards offer excellent insurance benefits for this exact type of situation. Whatever Southwest doesn't reimburse you for, your credit card might.
If you don't have a credit card with travel insurance, shame on you.
I'm just kidding - most people don't realize that even lower-tier cards come with insurance that could save them hundreds of dollars a year. Check out our Top Travel Cards page if you want to look at our recommendations.
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🌎 Some quick-hit travel tidbits to keep you distracted
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Here's some interesting further reading for you:
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✈️ My 2023 top travel hacking strategies
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Last week I gave you a summary of how I used points, miles, and credit cards to travel around the world in 2022.
Today, I wanted to give you a quick peek at what I have planned for 2023 so far, share the strategies I used to book it all, and finish off with some of my incredibly nerdy travel goals.
So far, here is what I have booked and planned for 2023, taking me up through the end of July.
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2023 is taking me everywhere from Greenland to Madagascar to Mongolia to Zimbabwe to the southern tip of South America.
Let me share a couple of strategies I'm employing this year to make this crazy travel map a reality:
1. Round-trip flights with foreign origins
Here's a quick piece of homework for you: go on Google flights and search for a round-trip flight from Montreal to Paris. Note the price.
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Now, search for a round-trip flight from Paris to Montreal on the same dates. Note the much lower price.
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Now I know what you're thinking... and no, I'm not a magician (though I did practice when I was younger and definitely didn't have a rough time in high school...).
It's just a fact that round-trip fares from Europe to North America are almost always significantly cheaper than the other way around.
So I'm modeling my entire year of travel off of this tactic. My "return" flight home from a trip to Europe is actually just the first half of a round-trip, the second half of which is booked sometime later in the year.
As long as I plan accordingly, I can keep a steady flow of round-trip itineraries that technically begin in Europe, saving me thousands of dollars over the course of the year.
Why spend 40,000 points to fly to Europe one-way when you can spend $300 or $400 to fly round-trip?
This way, I can save my points for tactic number two...
2. Using my points and miles for partner bookings
I'm a big aviation nerd. I take entire trips to obscure countries solely to fly on cool planes and/or airlines. For me, it's part of the fun of this whole travel hacking game.
I also find that miles and points are a fantastic way to do exactly that.
For example, I'm using my Aeroplan points to fly on Emirates Business class from Zimbabwe to Dubai in just a few short weeks.
In March, I'll be flying on Oman Air in their super-luxurious business class from Chennai, India, to Kuwait City via Muscat (one of my favorite cities in the world) - also using Aeroplan points.
Then I'm using even more Aeroplan points to fly on Air Mauritius from Paris to Madagascar, with a 5-day stopover in Mauritius. There aren't many ways to get to this part of the world on miles and points, so I consider this to be an excellent use of my hard-earned points.
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Another great example is Mongolia, which is also really difficult to travel to with points. Luckily, I'm using Delta Skymiles to book a Korean Air flight from Seoul to Ulaanbataar for only 15,000 miles, a much better deal than the $300+ cash tickets on that route.
As I showed you earlier, there are many ways to get between certain parts of the world like Europe. That's why 2023 will be the year of obscure partner airlines for me.
3. Letting trips build themselves
Sometimes I know exactly where I want to go and when, but sometimes I like to let a good deal lead the way.
For example, just a few days ago, I found a flight from Toronto to Tokyo for just over $400. On the surface, that might not seem crazy. But here's why it's going to work out really well for me:
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The flight is on Air Canada, where I currently have elite status. That means I can book an economy flight and use my status to upgrade myself to Premium Economy or Business class and rack up miles toward 2024 elite status.
Since I have elite status, I can also use my premium Wifi pass during the 14-hour journey, a factor that is important to me as a remote worker.
Finally, the fare is a "flex fare" rather than standard or basic economy, so I even have extra options should I need to change or cancel this flight.
So I bought the ticket! From there, I planned an entire 2-week around-the-world trip based on cheap tickets I found.
I found a nonstop flight from Tokyo to the Philippines on ANA for only 12,000 points, so I booked that.
From Manila, it only costs $50 to fly to Bandar Seri Begawan in Brunei.
Do you know anything about Brunei? I sure don't. Let's go learn about it!
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I carried on like this with stops in Malaysia, Chennai, Kuwait, and Paris before booking a round-trip flight from Paris to Toronto (see strategy number 1).
So that cheap and convenient plane ticket turned into yet another once-in-a-lifetime trip.
Not too shabby, eh?
I don't think I need to tell you this, but I will anyway: FareDrop is a fantastic way to get unbelievably cheap flight deals sent straight to your inbox so you can build a fun, spontaneous trip like mine (sorry, not sorry about the shameless plug).
Finally, I set some travel goals for myself. This is purely for the fun of travel and to challenge myself. Here's what I have:
- Fly on every Airbus A330-800neo in the world
- Travel to 50 countries (just in 2023)
- Fly on 100 flights in 2023
- Book and complete a trip entirely on points (including food and other expenses)
The first one is pure aviation nerd stuff. Only three airlines operate the beautiful A330-800neo, and they're all pretty obscure; Kuwait airways, Air Greenland and Uganda Airlines.
Kuwait and Greenland are already booked, and I am already scheming for a trip to Uganda where I have a few friends anyway.
As for the last goal, booking a trip entirely on points, that one will be challenging. I bet you didn't know there are ways to pay for your meals with miles and points...
... but we'll save that for another newsletter. 😉
Having fun goals like this inspires me to get creative with how I earn and redeem points and miles, and makes even the booking and planning process so much fun for me.
Anyway, I hope some of these strategies come in handy as you begin thinking about your own travel plans and goals for this year. I'm sure 2023 will come with plenty of travel hacking successes and failures, and I look forward to sharing them with you along the way.
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We are kicking off the year strong here at the Daily Drop. As we speak, Kara and Nate are drawing the grand prize winner of a luxurious trip to the Maldives. Typically, you'd need to wait until their video airs on Saturday to find out if you've won.
But I happen to know a guy and a gal who have given me permission to reveal the winner to Daily Drop readers in tomorrow's newsletter, so make sure you check it out!
Were you affected by Southwest's late December meltdown? What are some of your travel goals for 2023? Let me know by replying to this email or reaching out on social media.
See you tomorrow,
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