When you think of taking a vacation, some common themes are prevalent; exotic locals, preferred weather, good food, exciting activities and experiences, and above all else hours of relaxation and enjoyment of whatever you choose to do.

There are thousands and thousands of destinations world-wide, and many of them are far enough away to warrant flying to them instead of taking other forms of transportation. I have been in the travel industry since 2005, all of it working directly with travel agents, the flying public, and the airline companies directly managing international airfare, hotel, and car rental reservations.

Flying used to elicit illusions of grandeur; beautiful women serving you free drinks whilst sporting trendy outfits, well-dressed travelers filling the cabin with cheer and anticipation of their journeys ahead, and the admiration of and feeling of mystique about the pilot of the aircraft. Today, I conjure images of missed flights due to mechanical problems, poor customer service from crabby airline employees, confusing booking procedures and rules, and inflated fares complimented by phantom fees.

Planning, purchasing, and managing your flight bookings is an arduous task nowadays; I recommend you do not take this lightly. This will give you tools to book your own flights at the lowest price with confidence. There will be no mention of hotels or car rentals; I would need to charge you for that. There will be no guarantee that you will not have problems like canceled flights, name misspellings, or missing baggage. I can, however, guarantee when something goes wrong it will not be your fault.

The most important part of this process has nothing to do with you, your destination, or your vacation. Before you book anything you need to understand who you will be dealing with and where you will encounter these people. They stand between you and a truly fulfilling vacation. For ease of comparison I will give them recognizable names; President Bill Clinton, Grumpy, and Bart Simpson.

Meet President Clinton

President Clinton has an extremely professional demeanor, he presents himself well, and he is very articulate. He has you convinced he is the smartest one in the room, and for 90% of people this is true. President Clinton's only motivation is to make money off of you without you realizing he has done this.

President Clinton usually is found as a travel agent, but is known to frequent as an internet travel guru, blogger, or even worse your friend who travels a lot and wants you to use their credit card if you pay them cash (so they earn frequent-flier miles on your trip for free stuff you will never see).

President Clinton is a professional after all; he has great well-presented ideas, but is charging you way too much for them. The best way to deal with President Clinton is to pick his brain, make him feel like you need him, then take his ideas and book them yourself. You will save at least 10-15% doing this and know the advice you've been given is accurate.

Meet Grumpy

Everyone who has been inside an airport has at least seen Grumpy. He is either an airline employee behind the ticket counter, or is on the other end of the phone when you are calling customer service. It doesn't matter what you do or say; this person will be terse, passive aggressive, mean, and most definitely condescending.

Grumpy will “deal” with you in every manner possible, except for calm, thoughtful, or respectful. You might know less and may feel worse about yourself after speaking with Grumpy, and if you do, snap out of it. This is one of Grumpy's defenses and he will use it mercilessly. The best course of action is to engage Grumpy; talk to him, ask him his favorite movie.

You need to chip away at the rough exterior because, despite what you think his IQ might be, Grumpy holds the answer to your question and he knows it. (Do not, however, ask Grumpy his favorite destination. Grumpy has not traveled since he started working for the airline.)

Meet Bart Simpson

Bart Simpson is the most challenging to deal with, yet you two will have the least physical interaction. Simpson is found almost exclusively at the airport; as a baggage handler, ramp agent, ground crew member, and occasionally as a fellow passenger.

Bart doesn't care about you or the 45 minute connection you have in Atlanta, and by the time you see him he has probably opened your suitcase already. Fortunately enough for you he doesn't want anything you have.

Don't mistake Bart for Grumpy; Grumpy is unpleasant but he was selected to work a job assisting the passengers directly because he has the ability to do so. Management didn't even consider putting Bart anywhere near the passengers, they put him with the luggage, pets, and aircraft noise because he is ambivalent, arrogant, and shameless. If you have the unfortunate experience of having to face Simpson as an employee all you can do is pray. If you encounter Simpson as a passenger just get out of his way, nothing good will come from an interaction.

Booking Your Flight

With these people in mind we can move on to actually booking your flight. If there is a reason to beware of any of the above characters I will make you aware [President Clinton]. Good luck and safe travels!

  1. Decide on an itinerary. The larger airports (Boston) will traditionally have the lowest fares. However, smaller airports with strong route structures (Portland, ME) have competitive fares from time to time.
  2. Begin looking at prices 4-5 months before your travel date [President Clinton]. This is the best time to purchase a flight for the lowest price.
  3. Based on the prices you find above, select individual flights operated by the same airline [Grumpy]. If you book flights on multiple carriers then you potentially have to deal with each airline’s Grumpy. You may also not be able to assign seats or change your flights if they are operated by other carriers.
  4. Book your flight 3-4 months in advance yourself online; you know your name and all of the other details needed. If you call someone to do this, trust me, you are adding more people to the list of potential mistake makers.

When you book the flight do it using one of the following.

The airline directly on their website [Grumpy, Bart Simpson]: Booking with the airline directly is the best way to ensure you are getting what you think you are getting. If you do need service with the booking at least there is no middle-man.

Google ITA Matrix Search [President Clinton]: The matrix software is by far the best search engine on the market. You cannot book flights though the site but the pricing is accurate and you are redirected to the individual airline's website to book.

Flightfox: This goes without saying- as you can see there is no place here for Slick Willy’s shenanigans, chalkboard gags, or just plain grumps.

Good luck and safe travels!