Our Trip Fell Apart (But Our Points Didn't) — Plus How to Travel for Free with Kids
A Southwest delay killed our Charleston beach trip — but because it was booked on points, we walked away without losing a dime. Here's exactly how we unwound three different award bookings, plus a full breakdown of how to earn and use points to travel with kids for free.
Melissa was supposed to be recapping a family beach getaway to Wild Dunes, a Hyatt resort near Charleston. Instead, a cascading Southwest delay forced a last-minute cancellation — and this episode walks through how to cancel an award flight, an award hotel stay, and a rental car booking without eating the cost. Then it's a deep dive into the credit card and points strategy that makes free family travel possible in the first place.
In This Episode
How to cancel an award flight and get every point back
What really happens when you cancel a hotel award stay inside the cancellation window
Two ways to avoid a last-minute hotel cancellation fee
Why rental car bookings through travel portals (Capital One, Chase, Priceline) can get complicated
Why earning points is harder for families than solo travelers
The fastest way to earn points: credit card sign-up bonuses
Best starter cards for family travel (Chase Sapphire Preferred, Ink Business)
How to search and book award flights (Google Flights, PointsYeah, AwardTool, airline alliances)
What a repositioning flight or drive is, and when it's worth it
The Southwest Companion Pass strategy for families
Hotel points strategy for families (Hyatt, IHG, Hilton, Choice)
Practical tips for booking flights and hotel rooms with kids
Chapters
00:00 Intro & catching up 01:00 The Wild Dunes trip and the cancellation cascade 03:00 Unwinding the points: flight, hotel, and rental car 08:30 Why points are harder to use for families 09:30 Earning points: sign-up bonuses and transferable points 13:00 Booking award flights (tools, alliances, repositioning) 18:30 The Southwest Companion Pass 20:30 Hotel strategies: Hyatt, IHG, Hilton, Choice 25:00 Practical tips and wrap-up
Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.
Podden och tillhörande omslagsbild på den här sidan tillhör
Melissa Conn. Innehållet i podden är skapat av Melissa Conn och inte av,
eller tillsammans med, Poddtoppen.
