Scott sent us this reader success story!

 

Thank you so much for the opportunity to share—and for all the knowledge you’ve shared with us through your podcast. My wife and I are huge fans and loyal listeners!

My wife and I are both educators, and like many teachers, we’ve spent years pouring everything into our students and kids while quietly pushing travel dreams to the back burner. We always said we’d go somewhere amazing “someday,” but Hawaii always felt out of reach.

Then in January 2024, a friend introduced us to the Southwest Companion Pass and said, “If you play this right, you could be in Hawaii by summer.” That one comment sparked something in us.

By that summer, we each had a Companion Pass and flew our kids to Maui! We stayed in a vacation rental, cooked meals in the room to save money, and soaked up the experience. But we realized that we had only scratched the surface of what’s possible.

 

 

The 2025 Plan: Bring the Whole Family

As soon as we got home, we started dreaming bigger: what if we came back in 2025, but brought my wife’s parents along? They had never been to Hawaii, and with a little help, they were totally on board.

We also secretly coordinated with my wife’s brother and his partner to surprise her parents at the hotel. When they showed up unexpectedly, it was one of those moments that makes the whole trip unforgettable.

My in-laws said over and over again: “This is the best vacation we’ve ever had.”

 

 

How We Earned the Points

• Opened Chase Sapphire Preferred® Card and Chase Ink business cards (and referred each other back and forth)
• Achieved Discoverist status by opening a personal World of Hyatt Credit Card
• A generous points and mileage collector gifted us a Guest of Honor award and Club Access Award—so we could extend perks to our in-laws!

 

How We Booked It

Hotel: Hyatt Regency Maui

• 3 rooms for 5 nights using points (25k–35k points per night)
• After we booked, the hotel dropped a category, and we got thousands of points refunded!
• We opted out of housekeeping and earned 500 Hyatt points per night
• Guest of Honor + Club Access Awards gave us club lounge perks and waived resort fees

Cash value saved: over $13,000!

 

Flights: Southwest Airlines + Companion Pass

• We flew our family nearly free (paid taxes only)
• Tried out the new Chase Sapphire lounge in Phoenix

 

What We Did (That We Couldn’t Have Before)

• Helicopter tour over West Maui and Moloka’i
• Sunset cruise with three generations
• Resort beach + pool days
• Unlimited breakfast and snacks in the lounge
• Surprise family reunion moment we’ll never forget

 

What We Learned

• Older relatives can do this—it just takes a little help
• Chase Ink + personal cards + referrals = fast points
• Hotel categories can drop in your favor!
• Guest of Honor + Club Access = luxury we never imagined
• Your podcast was EVERYTHING. I listen weekly, and it gave us the confidence to pull this off.

 

 

Final Thoughts

This wasn’t just a vacation—it was a chance to give something special to our family. We’re regular people with modest incomes who found a way to make something extraordinary happen.

Thanks for helping us believe it was possible.

 

Related Posts

Reader Success Story: Four Generations in Hawaii

The Ultimate Guide to Using Points for Hyatt Hotels in Hawaii

Reader Success Story: Family of Five Island Hops in Hawaii