Learning From Literature

Take More Vacations by Scott Keyes

Take More Vacations by Scott Keyes

Take More Vacations: How to Search Better, Book Cheaper, and Travel the World by Scott Keyes is a travel book published in 2021.

Straight out of college in 2013, Keynes flew nonstop from New York City to Milan on a flight that typically cost $850 round-trip… He paid $130. 

At the time of his Milan flight, Keyes only made $34,000 a year but was dedicated to travel. He searched for the cheapest deals and started seeing success. Milan for $130. Belgium for $225. Vietnam and Cambodia using miles. Dominican Republic in business class for free using a voucher from getting bumped. His coworkers knew how much he made and didn’t believe it. He tried to explain that it all starts with cheap flights, but his colleagues still couldn’t understand because the way we search and plan our vacations is fundamentally broken. 

Scott’s book is his attempt to fix that misguided approach and ensure we all get a chance to see more of our world than we do today. With these low prices, you can take three or four trips for the price of one. It changes the question “Can I afford to go?” into “Do I want to go?”

To help others take advantage of his process, Keyes created an email list and website called Scott’s Cheap Flights (now called Going) which has over 2 million users. Airfare is erratic but not indecipherable; with a basic knowledge of how airfare works, anyone can relish the joy of cheap flights.

Some of the best deals Scott shared from last year includes:

Purchase the book by clicking this link!

Enjoy!

Table of Contents

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You Don’t Take Enough Vacations : The Curse Of Expensive Flights 
  • Travel = the #1 thing people want to do as they get older & commonly a top New Year’s resolution
    • However, we take the least vacations out of any point in recent history
    • US = 1 billion unused vacation days last year
  • #1 travel stressor → logistics (flight, accommodation, etc)
    • International travel = 2x the stress as domestic travel
  • Once you know how, it becomes exciting and empowering
    • Scott takes trips to Italy for $130 and Japan for $169 – of course it would be stressful if he had paid $1300 
  • Mental biases when buying airfare:
    • Loss Aversion
      • Feel more pain at prices going up than joy going down → lock in prices quick
    • Anchoring
      • Anchor your perception of a reasonable price based on what you paid previously
    • Recency Bias
      • Stable prices over the last few weeks are reasonable prices (NOT)
    • Sunk Cost Fallacy
      • If you mentally decide on a trip and then plan for it, not going because of high airfare doesn’t feel like an option
    • Wishful Thinking
    • Procrastination
  • It’s almost always possible to avoid expensive flights if you use cheap-flight strategies and don’t fall into common mental biases
  • There are times when expensive flights are unavoidable
    • If your grandma falls ill and has days to live, your flight options are quite limited
Travel As Medicine : How Cheap Flights Lead To Happier Trips (And More Of Them)
  • 2018 – 93 million Americans traveled abroad
  • Travelers are proven to be happier, healthier, and more productive than nontravelers 
  • Travel isn’t just correlated with better life outcomes, it helps promote them
    • As stress and anxiety decrease, mood and other things benefit
    • 93% of travelers feel happier after a vacation
  • Experiential spending boosts happiness more than material spending — memories, stories, relationships, etc. are perpetual enjoyment
  • Frequency of pleasurable experiences is more important for wellbeing than quality
    • Often better to have three one-week trips per year than one three-week trip
    • One vacation per year elevates the importance of it – you have to do everything and make it worth it
    • Multiple vacations per year allows you to visit places that may be further down on your list and allows you to relax during the trip. The worst case scenario is you don’t like the city much but you have another vacation in a few months
    • Excitement can begin when you return instead of being stuck in the same day-to-day life for the next year
  • Hedonic adaptation = overall happiness reverts to a baseline level even after a major shock like winning the lottery or losing a thumb 
  • Short intervals → there is no hedonic adaptation, you don’t have time to get used to it
  • How to stop hedonic adaptation is not having more wealth, but buying more experiences
    • Every experience is different, even getting drinks with friends
    • The stories, atmosphere, and circumstances are different
  • Cheap flights let you travel more often, but also allow you to have more money for things that could make the trip special like fancy dinners/cocktails, staying in a nicer hotel, etc. 
  • Flights = expensive → filled with resignation 
  • Flights = cheap → joyous 
    • Think how a vacation would feel if you went to Thailand for $560. Now think if you had paid $5,000. See the difference?

How most people plan a trip (Destination First) :

  1. Pick where
  2. Pick when
  3. Check flight prices 

If you want cheap flights, make it the priority (Flight First) : 

  1. See where cheapest flights are
  2. Pick one of the cheap flight destinations
  3. Pick one of the cheap flight dates
  • Optimize for cheap flights, don’t hope for them
  • Imagine all fights are $250 roundtrip. Where would you go?
    • Few of us have sat down and listed every place we’d visit if airfare were no concern
    • We have countless places we’d visit if flights were cheap, yet so many of us plan a vacation as though there’s only one place in the world in which we are interested
    • People handicap themselves
  • The Flight First Method doesn’t mean booking last minute, most cheap flights are 3-8 months in advance
  • If you try to hit a target the size of a bottle cap, your chances are pretty slim. If you try to hit a target the size of a tractor, you’ve got pretty good odds
    • The more you broaden your preferences, the larger your target, and the better your odds of finding a cheap flight
  • Broadening your target doesn’t necessarily mean sacrificing
    • After all, few of us have just one place in the world we want to visit
  • The right balance of price and convenience is different for every person
    • Cheap flights don’t have to be inconvenient 
    • Scott’s $130 Milan flight was nonstop and included checked baggage
    • There’s nothing wrong with picking a more expensive flight for the convenience, but do it consciously
Flexibility: Using It To Your Advantage (And What To Do When You Don’t Have Any)
  • Flexibility is #1 factor in getting cheap flights
    • Where to fly
    • When to go
    • When to book 
  • Keep an eye on driving-distance airports and short-hop airports
    • Think in total travel time, not flight time 
    • 35 hour flight versus 25 hour flight + 3 hour drive
    • Only makes sense when savings > inconvenience ($20 ticket savings is not worth the gas)
  • “Goldilocks Windows” = the periods when cheap flights pop up the most
    • Domestic
      • 1-3 months before off-peak season
      • 3-7 months before peak season
    • International
      • 2-8 months before off-peak season
      • 4-10 months before peak season
    • Earliest possible (year in advance) & last second flights (within 21 days) are always inflated
    • Don’t buy just because it’s in the Goldilocks Window, wait for an exceptional deal
  • Hotcakes Principle → the better the fare, the shorter it will last (so don’t wait too long if you see a good one!)
  • Usually you have at least one when/where flexibility
    • Honeymoon = where
    • Visiting family = when
  • If you don’t have when/where-to-travel flexibility, your last flexibility is when to book
    • Try to use the Goldilocks Window
    • Start monitoring as soon as you can and then ask yourself “Are prices more likely to go up or down?”
    • If you’ve been monitoring and the dates/location aren’t flexible (like a friend’s wedding) → priority shifts from being cheap to not getting ripped off
    • Any inflexible event → book Southwest → they allow free cancellations so you know you won’t ever have to pay more, and if the price drops you can cancel and rebook
  • Extra tips
    • Greek Island Trick (more in last chapter)
    • Alter travel dates by 1-2 days and see if that helps
    • Try nearby airports
    • Flights on Tuesday, Wednesday, Saturday + non-holiday weeks + non-summer months are usually cheaper (they try to exploit weekend business travelers and during summer it’s good weather + school is out)
  • If overwhelmed, just start by picking a place, season, or commit to going for cheapest price and book the first deal that pops up
  • Sometimes other factors take precedence over price but be aware, each additional need narrows the chance of a cheap flight
Then And Now : A Brief History of How Airlines Determine Prices
  • 1920s –1940s
    • Mail was the focus of air travel, not passengers (6x more profitable)
  • 1950s – 1970s
    • Became more mainstream with new technology such as pressurized cabins and toilets
    • Historic shift to multiple prices → high fares for convenient timed first-class flights and low fares for inconvenient “coach”
    • 1978 = Deregulation
      • Rates plunged since airlines could now charge whatever they wanted 
  • 1980s – Present
    • New airlines popped up (specifically “budget carriers”)
    • In response, airlines diversified income streams:
      • Airfare Price Discrimination
      • More Premium Seats Sold
      • Credit Cards and Frequent Flyer Miles
      • Ownership In Other Airlines (Example – Delta owns 49% of Aeromexico and Virgin Atlantic)
      • Corporate Contracts (business travelers account for 12% of seats but 75% of revenue. Apple pays United $150 million a year. Apple pays $35 million a year for just 50 business class seats a day from San Francisco to Shanghai)
      • Cargo
      • Add-On Fees
  • Airlines have figured out a business model that depends not on price-sensitive vacationers but on more reliable sources of income like business travelers, banks, and corporate contracts. In a sense, all these items are subsidizing economy traveler fares, making $300 roundtrip flights to Europe possible.
The Golden Age of Cheap Flights : How And Why Everyone Can Afford To Fly
  • People don’t realize how cheap flying has become
    • In 2018, only 13% of people correctly assumed airfare has gotten better
    • Since deregulation, prices have dropped 50% (inflation adjusted)
    • Average domestic roundtrip in 1981 = $638 → 2016 = $367 (Doesn’t even account for the fact flights have gotten 25% longer on average)
    • In 1965, only 20% of Americans had ever taken a flight → Now, 80%+ of Americans have taken a flight and ~50% fly in a given year
    • Prescription drugs have doubled inflation, DisneyWorld passes have more than tripled, college tuition has more than quintupled 
  • Most people overpay and therefore assume flights are expensive
Unpredictable And Irrational : Why Airfare Is So Volatile 
  • Prices do not increase/decrease gradually; there are wild swings
  • Price can go weeks without changing and then change multiple times in a day
  • 3 primary causes:
    • Autopilot Pricing (less inventory = higher price)
    • Unexpected Consumer Demand (more or less)
    • Competition 
  • Prices are higher because airlines try to discriminate business vs leisure travelers
    • The more you avoid business-traveler trends, the higher chance you’ll have a cheaper flight
    • Book months in advance, stay longer than 7 days, have a connecting flight, etc.
    • Sales usually happen 2-8 months out because most leisure travelers book a few months in advance. If sales were close to departure time, they risk cutting the high prices business travelers have to pay (who book late because they have less flexibility)
  • The more you remember that pricing is volatile, the less likely you are to settle for bad fare
The Fundamentals : Answers To Everyday Flight-Booking Questions
  1. There’s no single cheapest place to book flights, each has own advantages and drawbacks
    • Directly Through Airlines
      • Get ticket immediately (don’t risk fare disappearing within a few minutes)
      • Protected by 24 hour rule (full refund & no fees within 24 hours of purchase – as long as flight is in, from, or landing in the US and is 7+ days departure)
      • Altering itinerary is easier
    • Online Travel Agencies (Expedia, Priceline, Orbitz)
      • Show you dozens of carriers prices
    • Flight Search Engines (Google Flights, Kayak, Skyscanner, Momondo)
      • Shows many carriers but doesn’t book thru FSE’s (book thru OTA or direct)
      • Southwest doesn’t show up on FSE’s
      • Suggestion – search Google Flights then once you find a route, check Skyscanner/Momondo for a possible lower price
  2. Big cities get the highest # of deals but small cities get the best deals (most money off)
    • Common destinations to see an under-$500 roundtrip:
      • North America
      • Caribbean
      • Central America
      • Northern South America
      • Western Europe
      • China
    • Less likely destinations to see an under-$500 roundtrip (but still possible!):
      • Africa
      • Oceania
      • Middle East / Central Asia
      • Southern South America
  3. Fees:
  1. Don’t assume anything – always read about the fees before
  2. Not all basic economy flights are the same
  3. May be cheaper to prepay for optional items
  4. May be cheaper to pay main economy versus basic economy + checked bag

To avoid fees:

  • Bag Fees
    • Don’t check a bag
    • Use an airline credit card that gives you complimentary checked bags (includes all members of your group)
  • Advance Seat Selection Fees
    • Check in as early as you can (on some airlines = first come, first serve)
    • Ask someone to switch
  • Cancellation Fees
    • 24-hour rule
    • Medical emergency
    • Jury duty
    • Natural disaster or other major event
  • Change Fees
    • If your flight has a schedule change (even if only a few minutes), call and ask for your preferred flight
    • Basic economy usually can’t be changed/refunded
  • Southwest – The Destroyer of Fees
    • 2 free checked bags!
    • Open seating – whoever checks in first → boards first → picks their seat first
    • Free changes/cancellations 
      • Refund in Southwest travel credit that has to be used in 12 months
  • Full-service carriers usually have better options in the event of cancelation over budget airlines
Clear Your Cookies : Nine Flight-Booking Myths Debunked
  • Any time something is difficult to understand, it fuels rumors
  • Myth: Clear Your Cookies 
  • Myth: The Cheapest Fares Are On Tuesday At 1
  • Myth: The Cheapest Fares Are On August 23rd
  • Myth: Flights Are Only Cheap Because Of Coronavirus 
  • Myth: The Cheapest Fares Are Last Minute
  • Myth: Dressing Nicely Will Get You An Upgrade
  • Myth: Wait For Advertised Sales
  • Myth: One Airline Is Always The Cheapest 
  • Myth: Flying Was Better Back In The Day
    • Used to be incredibly expensive and long
    • NYC – Rome
      • 1948 → $9,000 (inflation adjusted) and 20 hour travel time
      •  Today → as low as $248 and 8 hour travel time
    • Planes were filled with cigarette smoke and crashed more often
    • Forget even imagining Wifi, TV screens in the seats, etc.
    • Minorities couldn’t fly until the 1960s and female flight attendants were required to be aged 21-26, height 5’2-5’6”, weight 100-130 pounds, and marital status of single
Should You Take That Trip? How To Think About Overtourism and Emissions
  • CO2 Emissions
    • 2.4% of global CO2 emissions are planes (~10% is industrial heat but when do you hear complaints about that?)
    • An average 160-pound person flying Denver – Boston would add a marginal fuel cost of $8
    • Your contribution to emissions
      • Directly
        • If the route is available to purchase, that means the plane is going to fly no matter if you’re on board
      • Indirectly (by incentivizing airlines to add more flights)
        • The less you paid for your ticket → the less incentive you give the airline to fly more
        • Airlines don’t make decisions based on the behavior of a single individual – they decide the amount of flights by profit, not by # of people
        • Therefore → cheaper flights = less flights = less carbon
    • Not every passenger is equal → Premium seats have more room and therefore more emissions per person
      • First-class passengers have 9x higher footprint than coach passengers
    • At the bottom of the matter, individual choices aren’t enough, it is necessary for all of society to change → If you taking that flight directly won’t add anything and your cheap ticket loses the airline money (and so isn’t an incentive to add more flights), there’s no reason to feel guilty
    • Carbon Offset – counterbalance your share of a flights emissions by putting money towards a carbon reducing project 
  • Overtourism
    • There’s always places to go without people (skip Disney World, the Louvre, etc.)
      • It can be disappointing when a site gets crowded but you don’t own it
    • Regulation is needed to protect places so future generations can enjoy them and promote sustainable travel
      • BUT it’s not a solution to shame people for traveling, especially considering all benefits for tourists and hosts
      • Regulation is the governments’ job
    • Tourists behaving poorly grabs the media’s attention (by the way, poor conduct isn’t just confined to visitors), but not enough tourism is a far more dangerous threat
      • When tourism is on the line (usually a significant amount of GDP), the financial incentive makes it easier to maintain the sanctity of a destination 
      • Without visitors, there’s no incentive to keep it up
      • Example – if no one visited Machu Picchu → the government and locals wouldn’t get any money from tourists visiting → there would be no incentive to keep it in good condition
  • Travel isn’t a personal indulgence → Besides the physical/mental benefits for tourists and financial benefits for hosts, understanding other cultures and sharing the concept of humanity is a mounting necessity in our times
The Unexpected Joys Of Travel : How To Get Better At Vacationing
  • The more you travel → the better you get at it → the more you enjoy it
  • It’s a skill set – you aren’t born knowing how to navigate airports, foreign neighborhoods, book flights/accommodation, etc.
  • Frequent travelers are better at formulating trips they will personally enjoy
    • The more we travel, the more we discern what we hate / what we love about traveling and then we can structure future trips accordingly
    • If you read a mystery book and hate it, you don’t hate reading, you might just hate mystery
  • Our motivations also can shift — what we look to get out of our trips evolves
  • When we take a risk and it turns out poorly, it is regretted only in the short term
    • The lasting regrets come from risks we didn’t take
    • 74% of regrets from elderly people were things they chose NOT to do
    • We hamstring ourselves with anticipated regret (that we actually wouldn’t ever feel)
    • Fading Affect Bias — negative experiences lose their salience over time
    • Don’t let a fear of bad experiences prevent you from getting out there
  • Research shows happiness peaks BEFORE the vacation
    • It’s not a trip itself, but just the concept of traveling that we associate with happiness
    • Planning a vacation in advance gives you more time to anticipate
    • The more you anticipate → the more you end up putting vacation in a rosier light, confirming your biases
    • Waiting for an experience promotes significantly more happiness, pleasantness, and excitement than waiting for a material good
  • The next happiest part of traveling is making memories, STILL not during the trip
    • The immediate afterglow a trip can fade but the memories will be joy forever 
    • Peak End Rule – happiness remembered not by the average feelings but by emotions at the most vivid + final moments
    • What defines a story are changes, significant moments, and endings
Pro Tips : Advanced Flight-Booking Tactics To Maximize Your Vacation
  • Greek Islands Trick
    • Pick the cheapest flight near your destination, then make a short hop
    • Newark – Santorini = $1500 
    • Newark – Athens = $294 + $40 hop to Santorini = $334 total roundtrip
    • Another benefit is you can stagger your itinerary dates to give you as much time as you want in the first destination
  • Build your own layover
    • Allows you to add as many destinations you want on a trip without spending any extra  
  1. Take advantage of a long layover in your flight itinerary 
  2. Bookend Technique — buy the bookend flights (outbound and return) but leave the middle to book separately 
    • Make the outbound and returning flights from 2 different cities
    •  Fly into Hong Kong and leave from Seoul
    • Therefore, you don’t have to pay for extra flight to get back to Hong Kong when you already saw it
    • Space flights a day or two in case of cancellations/delays
  • 24-Hour Rule
    • No cancelation fees 
    • Allows you to lock in a great fare even if you aren’t 100% sure yet
    • Allows you to switch if a better flight pops up after booking
  • Mistake Fare
    • When airline accidentally sells a flight at a cartoonishly low price
    • NYC – Milan $130, San Jose – Osaka $169, Boston – Iceland $100
    • Hotcakes Principle — the better a fare, the shorter it lasts
      • Mistake fares are the best of the best and very rarely exceed 6 hours, they can disappear any minute so act quick
    • Can’t be retroactively charged more
    • Over 90% of airlines honor mistake tickets – even if they don’t, you get fully refunded for ticket, fees, and any other nonrefundable plans made (hotel, car, etc) — after two weeks if you haven’t been notified, then assume it was honored
    • They are rare so instead of searching 24/7, let experts do it for you! (use Scott’s company Going!)
  • Hidden city ticketing
    • Distance is irrelevant to pricing 
    • Connecting flights cost more even though you fly farther than direct 
    • Newark – Orlando = $121
    • Newark – Orlando – Richmond = $88
    • Book the connecting flight and just skip the last leg
    • Not illegal or immoral (airlines forbid the practice though and if you do it many times in a row, they can strip you of your frequent flier miles)
    • Skiplagged finds hidden city tickets for you
    • Usually works when you want to visit a major hub where a connection would be anyway
    • Rules:
      • Don’t tell airline workers
      • DON’T CHECK A BAG
      • Only works on a one-way flight or the last leg of your itinerary — the airline cancels your itinerary as soon as you miss a flight
  • Thanksgiving
    • Super expensive domestically
    • Cheaper internationally
    • Dallas – Rome = $300, Charlotte – Montreal = $243, San Jose – Beijing = $294
  • Points and Frequent Flier Miles
    • Miles = associated with a particular airlines + collected from your previous flights with that airline
  1. Miles are not the same between airlines
  2. You can’t transfer miles between airlines
  3. You can redeem miles for flights on partner airlines
  4. It’s expensive to transfer miles between accounts
  5. You can redeem your miles for someone else’s flight
  6. Watch out for big fees on some award flights
  7. Unlike cash, miles are great for one-way international flights (normally more expensive but cost less miles)
  8. You don’t earn miles on award flights
  9. Most miles come from credit cards, not flying
  • Credit Card Points = associated with particular bank/company + collected from making a purchase with that company
    • You can convert to cash or convert to miles (which you should do depends on the analysis)
    • Only a handful of financial institutions issue points (Chase, Citi, AmEx, CapitalOne)
    • Depends on what card you use how much value you get per point
    • Normally 1:1 converting points-miles but can have limited time bonuses
  1. Not all points transfer to all mileage programs (Chase can transfer to United but not Delta and vice versa for AMEX. Find current list on bit.ly/pointstransfers)
  2. You can transfer points to another person’s account 
  3. You can pay with points for someone else’s flights
  4. You can pay with points on almost all airlines 
  5. You can’t undo points transfers 
  6. You earn miles on flights you paid for with points (paying with points is the same as paying with cash)
  • Should I Pay With Cash, Points, or Miles???
    • Compare points/miles to cash price to determine the value you are getting
    • 60,000 miles or $1200 = you’re paying 2 cents per mile
    • 60,000 miles or $450 = you’re paying 0.75 cents per mile (better!)
    • Don’t pay with points if you are just getting one cent per point, you can get better value waiting for an award flight
    • If you have a credit card that gives automatic higher value to points (like Chase Sapphire Reserve which gives 1.5 cent value), it can make sense especially if you fly economy
  • Pay With Cash Or Points When:
    • You found a cheap flight 
    • You have elite status  (eligible for complimentary upgrades / earn faster miles)
    • You can’t find award availability for a flight you want (availability is variable and blackout dates over peak season)
    • You have a preference for simplicity
  • Pay With Miles When:
    • No cheap flights are available 
    • There’s an award flash sale 
    • Business class redemptions (miles for business class is usually good value – mega expensive with cash)
    • If you have a ton of miles 
Conclusion
  • The best memories are the unexpected ones, the experiences we couldn’t anticipate 
  • Travel is more than just an escape, the memories we develop are transformational 
  • Three cheap flights  in particular, that change Scott’s life
  1. $130 to Milan – prompted him to share his love of cheap flights with others 
  2. $200 flight to Puerto Rico – unexpectedly met someone on the beach; they kept in touch and visited frequently
  3. An award flight (free) to Hong Kong – after a hike of Victoria Peak, he asked the woman from that beach in Puerto Rico to marry him
  • We know travel is a transformational undertaking, but precisely how it will transform us is impossible to predict
Other Tips Throughout the Book
  • Some credit cards include travel insurance
  • Accommodation/Hotels
    • Google Hotels
    • Airbnb/Vrbo
    • Roomer – where you buy people’s nonrefundable accommodation for a fraction of the price
    • Booking Directly – can save if you call directly versus booking on an OTA
  • Costco Travel — cheapest car rentals plus no cancellation fee
  • When traveling with a group, check to see if fares a cheaper by booking one or two at a time
  • When your flight gets canceled:
    • Do your own research on other flights that would work
    • Call international customer support if US support is booked up
    • Ask for compensation if it isn’t weather-related
  • The US government only allows planes within its borders that have been approved by the Federal Aviation Administration (which evaluates safety protocols, oversight, and training, etc.)
  • Lifetime odds of dying in a plane crash = 1 in 10,000 (compared to in a car = 1 in 114, bicycle = 1 in 4,486, and walking = 1 in 647)
  • Cost-Effective Ways To Get Business Class:
    • Use miles
    • Get bumped for compensation
    • Bid for upgrades at check-in
  • Global Entry lets you skip the normal immigration and customs line when returning from abroad and includes TSA Precheck (it’s only $15 extra)
  • If you’ve got flexibility in your schedule, volunteering to get bumped can be a big windfall
    • Scott has gotten $900 when an airline oversold his flight and a friend of his once got $10,000
    • The key is to know everything is negotiable to them so bargain high
    • Doesn’t have to be cash but can also include perks like business class, better routing on a replacement flight, meal vouchers, etc.

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