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Sometimes travel planning goes perfectly. Sometimes a sick child cancels an international trip less than 48 hours before departure.

This week, Richard shares the story of how a long-planned family trip to London unraveled at the last minute, what he learned while canceling flights, hotels, and activities, and how a father-daughter staycation in New York City helped salvage the weekend.

The conversation also dives into using AI to build family travel itineraries, including how Richard used Claude to create a detailed London plan complete with maps, transit instructions, and daily schedules.

Ed recounts a frustrating travel day involving delayed flights, rental car headaches, and the challenges of fixing travel disruptions even with top-tier airline status.

Plus, Richard takes a chance on Frontier's GoWild Pass, Ed reports more positive experiences with Hilton Diamond Reserve treatment, and the guys react to a jaw-dropping United seat assignment price for an economy flight to Europe.

 

 

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✈️ What We Cover in This Episode

✈️ Richard's canceled London trip
• A last-minute illness changes everything
• Unwinding flights, hotels, and activities
• Lessons from travel plans that fall apart

✈️ A father-daughter New York staycation
• Park Hyatt New York
• Eloise Tea at The Plaza
• Creating travel memories closer to home

✈️ Using AI to build better itineraries
• Planning London with Claude
• Maps, transit routes, and daily schedules
• How AI is changing trip planning

✈️ Why travel disruptions remain frustrating
• Flight delays and limited information
• Rental car reservation challenges
• The reality of fixing travel problems in real time

✈️ Hilton Diamond Reserve update
• Additional stays since qualifying
• Surprising recognition and amenities
• Early impressions of the program

✈️ Frontier's GoWild Pass experiment
• Richard buys the promotional pass
• How availability really works
• Whether the value proposition holds up

✈️ Alaska's new Iceland service
• Seattle to Reykjavik on a 737 MAX
• Narrowbody flights across the Atlantic
• Would either of them actually book it?

✈️ Bank of America Preferred Rewards changes
• New qualification requirements
• Why longtime users may lose value
• What it means going forward

✈️ United's eye-opening seat assignment pricing
• Economy Plus pricing to Europe
• Standard economy seat costs
• The surprising economics of seat selection

  

⏱️ Episode 439 Timestamps 

0:48 – Richard's London trip is canceled at the last minute

6:12 – What happens when a family trip falls apart

8:34 – The father-daughter New York staycation

10:58 – Using AI to build travel itineraries

17:07 – Travel disruption headaches: delays, rentals, and rebooking

25:48 – Hilton Diamond Reserve delivers another surprise

28:03 – Richard buys Frontier's GoWild Pass

34:31 – Alaska launches Seattle–Iceland service

37:19 – Bank of America Preferred Rewards changes

38:58 – United's shocking $329 seat assignment fee

 

 

 

 

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Podden och tillhörande omslagsbild på den här sidan tillhör Ed Pizza, Richard Kerr. Innehållet i podden är skapat av Ed Pizza, Richard Kerr och inte av, eller tillsammans med, Poddtoppen.