Flights for a Steal

My methods will primarily resonate with the busy white-collar American - someone with a full-time job and a decent amount of time off but difficulty taking it. Europeans with their 2-3 months of time off would read this list and scoff at the absurdity.

Timing

Until Elon Musk builds us some cross-world hyperloops, I'm resolved to optimize my schedule to maximize the time spent at the destination. Though I've been fortunate to work in places with generous time off policies, the fact of the matter remains that it's very hard to take off 2 weeks at a time when the world (and the business) keeps moving forward. What to do? Time hack. 

I follow a few simple guidelines. Obviously these won't work for everyone.  

1. Fly out on a Thursday/Friday evening. You can work during the daytime and not spend a day on transit. 
2. Fly back on Sunday afternoons or red-eye Monday morning. In the past I've been known to land at 5am and be at the office by 9am. It doesn't feel great, but nothing that an extra coffee and pre-workout can't fix. They say the second part of your life starts when you discover you can have pre-workout and *gasp* not go to the gym after.  
3. Take advantage of 3-day weekends. A holiday like Memorial or Labor day means taking 5 days off for the price of 4. If you leave the prior Friday and return the following Sunday, that's a 10 day vacation!
4. Skip town on Thanksgiving. Similar to above, taking off on Friday and coming back the following Sunday is a 10 day vacation for the price of 3 days. 
5. Take a longer trip over Christmas / New Years. In my line of work, business is slow this time of year. That means I can take off ~14-20 days guilt free and not be worried about cellphone signal. 
6. Work remotely from the destination. While I prefer to not be cooped up in my room on zoom meetings looking out the window wistfully, sometimes it's more economical to fly out earlier/later and spend a few days working from your vacation destination.
7. Changing companies? Negotiate a later start date. When you sign a new offer, negotiate to not start for an extra 3-4 weeks. It's the only time you get to take that much time off at once and not have a care in the world. They probably spent months finding you, a couple extra weeks won't make a difference. However, it will make a huge difference in your mindset once you're properly recharged and ready to tackle a new chapter. Can you tell I've used that line before? 

Finding Cheap Flights

Scott's Cheap Flights. The BEST source of flight deals on the internet. I'm on several other flight tracking email lists, but 95% of the time it's the deals from Scott's emails that determine my next travel destination. I've been a premium member for 5+ years and my membership for that entire time period has more than paid for itself. My best deal was a mistake fare to Croatia for $364 (normally $1100+). If you're not already a member (there is a free tier), check it out!

Escape. This flight search engine is similar to Google's Explore functionality, but more user friendly. It lets you see flights to anywhere in the world in your price range. 

Momondo. Once I've found a deal and dates I like, I go to Momondo search to see if I can find the fare for a bit cheaper elsewhere. The caveat is that often times to get that fare you have to purchase on an agency website, which can be very painful if you need to make a change to your itinerary later. What to do instead? If you have a credit card that price matches flights, book on your card's travel center and then ask for a price match (more details in this post).  

Google Flights. Everybody knows about this one, but its still worth mentioning. I like to use the Explore tab to get ideas for potential trips. I also use the flights search to 1) look up flights from different airports and 2) set up alerts. 

For more cheap flight tips, check out this article from Scott's Cheap Flights. 

VIP Tips

1. 2-Itinerary Hack: The best flight deals are often from the major international airports around New York, Boston, Miami, LA, or SF. What to do if you don't live around there? Buy two itineraries - your international flights from that airport, and your domestic flight from your home airport to the departure airport. 
1. Example (true story): I got a flight alert for fares to Buenos Aires from Boston for ~$550 through JFK. The fare from Atlanta to Buenos Aires was $~1100, also through JFK (I respect and loathe demand pricing). A roundtrip from Atlanta to Boston is about ~$200 (or "free" if I use points). If I want to make it even more hacky, I'll buy a one-way to Boston (since I must start my itinerary there), but on the way back buy a one-way from JFK to Atlanta. 
2. Don't check your luggage! Especially if you have multiple itineraries. Assume that flights will be delayed - and when that happens, you have many more options (including sweet talking the nice lady to get you on the next flight out or sprinting to your next gate) when all your baggage is on your person. 
3. Start your real vacation at the farthest point: Usually I will buy a roundtrip to a major international city, and then a series of one-way flights to the farther destinations. I start out with the one farthest out and make my way back. Why? First, the additional domestic flight will be cheaper than if you had booked from your origin. Second, you reduce the number of times you have to go to the airport, which is at least 4 hours a pop. 
4. Get a credit card with lounge access: As someone who hasn't yet made it up high enough in the world to not fly cattle class (read: economy), being treated like a real human being for the brief hours before the flight is absolutely divine. There's always free food and drinks (quality varies) and sometimes showers and nap pods. Its typically more quiet and the wifi is far superior. Additionally, the built-in travel insurance on the card means you don't need extra travel insurance. For more thoughts on this, check out my other post on money matters. 
5. Turn off the in-flight entertainment: Transit is a great time to catch up on deep focus work. There is literally nothing to distract you except that annoying voice in your head (hopefully just your own). Read a book on your kindle. Do some work on your laptop. You'll feel productive, not like you just binge-watched 10 hours of mindless tv. 
6. A non-boozy aid: If I really need to catch some z's on a long haul or red-eye, I will usually take a sleep aid like Unisom. While my fellow Russians may praise vodka as their savior to the Ultimate Question of Life, the Universe, and Everything, the reality is that alcohol combined with airplane pressure makes you feel worse.