Take More Vacations by Scott Keyes

Take More Vacations by Scott Keyes shows how travelers can turn airfare into a tool for adventure, not a barrier. After jaw-dropping deals – like $130 round-trip flights to Milan and free business-class trips – Keyes realized that most of us simply misunderstand how airfare works. 

In this book, he shares the strategies behind finding travel deals, making the question less “Can I afford it?” and more “Where do I want to go?”

The Curse Of Expensive Flights 

• Travel is the most common #1 aspiration, yet Americans take fewer vacations than ever
• Main stressor = logistics
  • Cheap flights ease stress
  • Example: Italy for $130 or Japan for $169 is less stressful than paying $1,300
  • More affordable = more frequent travel + extra money for experiences
• Common airfare mental traps
  • Loss Aversion: Panic when prices rise, rush to book
  • Anchoring: Think today’s price is high if you once paid less
  • Recency Bias: Assume recent prices are the norm
  • Sunk Cost Fallacy: Feel committed once you plan
  • Wishful Thinking / Procrastination: Delay and miss deals
• Most expensive flights can be avoided – except last-minute emergencies

The Flight First Method

• How most people plan (Destination First)
  • Destination
  • Dates
  • Flights
• Flight First Method (for cheap flights)
  • Cheapest flights
  • Choose destination based on affordable options
  • Pick dates based on cheap flight availability
• Why Flight First works
  • Imagining all flights cost $250 roundtrip lowers the barrier to travel
  • Narrowing choices is like aiming for a small target – odds are low
  • Expanding options increases the chances of finding affordable flights

Flexibility

• Flexibility = key to cheap flights
• Goldilocks windows
  • Domestic: 1–3 months before off-peak, 3-7 months before peak
  • International: 2–8 months before off-peak, 4-10 months before peak
• Early or last-minute flights tend to be inflated
• Hotcakes Principle: Great fares disappear quickly – don’t wait too long
• Other strategies
  • If inflexible, prioritize booking early
  • For fixed plans, book Southwest for free cancellations and rebooking
  • Try shifting travel dates or airports to find better deals
  • Avoid business traveler trends!

History of Airline Prices

• 1920s-40s → focus on mail, not passengers
• 1950s-70s → more mainstream with pressurized cabins, toilets, etc; introduction of multiple fares
• 1978 → deregulation, significant drop in prices
• 1980s-Present → rise of budget carriers and diversified revenue streams (premium seats, cargo, add-on fees)
  • Corporate contracts and business travelers now heavily subsidize economy fares

Pricing

• Airfare costs have dropped significantly
  • Since deregulation, prices have fallen 50% (inflation-adjusted)
  • Average domestic roundtrip dropped from $638 in 1981 to $367 in 2016
  • People overpay and assume they’re expensive, while other costs like prescriptions, Disney passes, and college tuition have risen much more
• Why is it so volatile?
  • Autopilot Pricing: less inventory = higher prices
  • Consumer Demand: fluctuates unexpectedly
  • Competition: affects pricing

Flight-Booking Myths Debunked

• 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
  • 1948 NYC to Rome → $9,000 (inflation-adjusted), 20-hour flight
  • Today → As low as $248, 8-hour flight with modern amenities

Pro Tips

• Greek Islands Trick: Book a cheap flight to a major city then take a budget hop to your destination. Stagger your itinerary for flexibility.
• Bookend Technique: Buy outbound and return flights from different cities to save on travel costs (e.g., fly into Hong Kong, leave from Seoul).
• 24-Hour Rule: Secure a great fare with no cancellation fees for 24 hours, allowing you to rebook if a better deal appears.
• Mistake Fare: Airlines accidentally sell flights at extremely low prices. Act quickly as they usually last under 6 hours.
• Hidden City Ticketing: Book a longer connecting flight and skip the last leg to save on costs. Don’t check bags and don’t do it repeatedly.
• Thanksgiving Travel: Flights are expensive domestically, but international trips may be cheaper (e.g., Dallas to Rome for $300).
• Points & Frequent Flyer Miles