Buying Points Like a Pro: The Strategy Behind Smarter Travel with @Travelliketommy (Ep. 84)

Published August 14, 2025

In this episode of Revolutionizing Your Journey, DeAndre Coke sits down with full-time traveler and points strategist Tommy Lonergan to dive deep into the world of buying points and miles. Tommy shares his journey from a traditional career path to building a lifestyle fueled by travel rewards, and he breaks down when and why buying points can be a smart move.

From credit card strategy to point valuations, they explore how to identify the best opportunities, what red flags to avoid, and why understanding the numbers behind point purchases is essential. Tommy offers insight into his favorite programs, including Hilton, IHG, and Air Canada, and stresses the value of long-term planning for luxury travel.

This conversation is packed with actionable tips for both beginners and seasoned travel hackers—ideal for anyone looking to upgrade their travel game without overspending.

 

Key Highlights:

  • Tommy’s journey: He has been traveling full-time for over four years, using points and miles.
  • Buying points: Strategic point purchases can unlock significant travel savings.
  • Research is everything: Understand redemption options before making a purchase.
  • Best programs: Hilton, IHG, and Air Canada are standouts for earning points through purchases.
  • Promotions matter: The right bonus can significantly shift the value equation.
  • Cost benchmarks: Aim to buy points for under 1.5 cents each.
  • Elite status tips: Combine point purchases with status benefits for maximum value.
  • Avoid bad deals: Stay away from third-party brokers and inflated rates.
  • International angle: Different regions have varying access and rules.
  • Plan with intent: Have a clear travel goal in mind before investing in points.

 

Resources:

 

Interested in Financial Planning?

 

Some of Our Favorite Tools For Elevating Your Points & Miles Game:

Note: Contains affiliate/sponsored links

 

Connect with DeAndre & Taryn: 

 

Connect with Tommy: 

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Written by

Bakir

Bakir is a travel and points & miles writer at BoldlyGo, sharing tips on flight deals, business class travel, hotels, credit cards, and travel rewards to help travelers get more value from their miles and points.