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Kyle Stewart

1451 Articles

Pittsburgh, PA
Kyle is a freelance travel writer with contributions to Time, the Washington Post, MSNBC, Yahoo!, Reuters, Huffington Post, Travel Codex, PenAndPassports, Live And Lets Fly and many other media outlets. He is also co-founder of Scottandthomas.com, a travel agency that delivers "Travel Personalized." He focuses on using miles and points to provide a premium experience for his wife, daughter, and son. Email: sherpa@thetripsherpa.comEmail: sherpa@thetripsherpa.com
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HiltonHilton HHonors

Hilton’s Diamond Reserve Rumor Raises Real Program Questions

Kyle Stewart Posted onNovember 9, 2025November 9, 2025 5 Comments
Hilton Virginia Beach Oceanfront standard guest room

Hilton may add a Diamond Reserve tier with big spend rules. Here is how it stacks up to Marriott Ambassador and what it means for Aspire cardholders. Hilton’s Next Move At The Top Hilton Honors is reportedly cooking up...

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Hyatt

Hyatt Hotels: Relying On Chase Deal as Growth Levels Off

Kyle Stewart Posted onNovember 9, 2025 4 Comments
Park Hyatt London River Thames Park Suite River View Deluxe living room angle

Hyatt posts a small RevPAR gain, plans big asset sales, and leans on a richer Chase partnership while demand signals look flatter across the industry. Setting The Table Hyatt’s third quarter (2025) reads like a mix of steady progress...

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Travel

California Candidate Says Ground Billionaire Jets

Kyle Stewart Posted onNovember 9, 2025 74 Comments
FAA Reductions Rep Katie Porter

Katie Porter says cut private jets, not commercial. With a 10% flight reduction looming from the shutdown, is she right about where to trim? FAA Reduction: Why Airlines Are Being Told To Fly Less Because of the ongoing government...

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Southwest Airlines

Southwest Business Class, Lounges, Europe Flights Inevitable

Kyle Stewart Posted onNovember 2, 2025November 2, 2025 6 Comments
a plane on the runway

Southwest Airlines has openly explored the possibility of adding business class, airport lounges, flights to Europe, and new aircraft – but it’s not if, it’s a matter of when.  Southwest Will Move Into Premium Expansion, Here’s Why Management at...

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Travel

Thanksgiving Travel Faces A Shutdown-Sized Stress Test

Kyle Stewart Posted onNovember 2, 2025November 2, 2025 25 Comments
PIT TSA Precheck Global entry delays

Record holiday demand meets a federal shutdown. Here is why Thanksgiving week could be a mess, and what changes if Washington flips the switch in time. A Perfect Storm For America’s Busiest Travel Week Thanksgiving is not a normal...

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American Airlines

American Airlines: Whole Trip Upgrades Often Cheaper

Kyle Stewart Posted onNovember 2, 2025November 2, 2025 5 Comments
a row of seats in an airplane

On a recent domestic trip, I was offered upgrades on American Airlines. However, when re-pricing the trip, I found it was cheaper than upgrading the segments.  Upgrade Offered I recently had a short trip for which I redeemed a...

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Disney

Second Guest Dies at Disney World’s Contemporary Hotel

Kyle Stewart Posted onOctober 26, 2025 7 Comments
Disability Access Services Disney Universal

A guest death at Disney’s Contemporary Resort casts a shadow over the magic of Walt Disney World. The Scene Behind the Headlines Last week at Walt Disney World’s Contemporary Resort at the edge of its Magic Kingdom park the...

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Travel

Younger Pros Turn Work Trips Into Lifestyle Upgrades

Kyle Stewart Posted onOctober 26, 2025October 26, 2025 6 Comments
impression by secrets isla mujeres waterslide

Hotels.com finds Gen Z and Millennials use business travel to upgrade hotels, meals, and rewards, and they post it all while stretching trips for fun. Background Business travel is not just a commute with a carry-on anymore. According to...

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American Airlines

Isom, American Airlines, May Never Escape Crushing Debt

Kyle Stewart Posted onOctober 26, 2025October 26, 2025 21 Comments
American Airlines Boeing 777-200 China

American Airlines’ ever higher pile of debt may never be paid off, meanwhile investors continue to support Isom, and give management a pass. Why? American Airlines Q3 2025 Earnings Call Lowlights American Airlines reported in its third quarter 2025...

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American Airlines

AI And Apathy? American Airlines Service Suffers

Kyle Stewart Posted onOctober 26, 2025October 26, 2025 15 Comments
American airlines coach

A personal experience highlights the many service challenges that American Airlines continues to face – both technical and by staff. Tech Glitch Plays Musical Chairs It was a dark, and stormy night – a Thursday night consultants’ special –...

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Europe

Biometric Border Entry Begins Across Europe

Kyle Stewart Posted onOctober 19, 2025October 19, 2025 8 Comments
Passport Control Brussels Airport

Europe just switched on biometric border checks. Here is what the new Entry/Exit System means for your next trip and how to get through quickly. Europe Flips The Switch On EES The European Union has begun rolling out its...

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Travel

Airbus A220 Engine Woes Ground 22% of Fleet

Kyle Stewart Posted onOctober 19, 2025October 19, 2025 15 Comments
Air Baltic Airbus A220 taxiing

New data pegs A220 groundings at roughly 22% while fresh reports suggest far more inspections are looming. Here’s what that means for flyers and airlines. A Shiny New Jet With Defective Engines Bombardier’s clean-sheet narrowbody, rebadged as the Airbus...

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Disney

Tragic, Mysterious Suicide at Disney’s Contemporary Resort

Kyle Stewart Posted onOctober 19, 2025October 19, 2025 10 Comments
Disney Contemporary Resort via wiki commons

A 31-year-old Disney fan died by suicide at the Contemporary Resort. Here is what authorities and local reports confirm, and what remains unverified. Tragedy At The Most “Magical” Address There are stories I wish I never came across, and...

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Travel

American Airlines Worse Than Frontier, Ryanair in Satisfaction

Kyle Stewart Posted onOctober 12, 2025October 12, 2025 10 Comments
American Airlines 777-300ER

An analysis of reviews, Skytrax scores, complaint searches, and incidents ranks the most frustrating airlines. American tops the list, though the context matters. Dissatisfaction Scores Paint Bleak Picture Air travel can be brutal no matter where you are in...

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Safety

Helicopter Crash Injures Five on Huntington Beach Oceanfront

Kyle Stewart Posted onOctober 12, 2025October 12, 2025 5 Comments
huntington beach helicopter crash - credit @LangmanVince on X

A helicopter went down near the Hyatt pedestrian bridge in Huntington Beach, sending five people to the hospital as federal investigators respond. Background The city of Huntington Beach is no stranger to attention from the air. Air shows, banner...

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Hotels

PAN AM HOTEL Takes Off: The Airport Stay Reimagined

Kyle Stewart Posted onOctober 12, 2025October 12, 2025 14 Comments
pan am hotel lobby proposed

JP Hospitality brings back the golden age of air travel with the launch of PAN AM HOTEL with a mid-century design, futuristic flair, and 24/7 service. Reviving the Spirit of Jet Age Glamour Airport hotels are rarely the highlight...

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thai airways

Thai Airways Introduces Lie Flat Premium Economy Plus

Kyle Stewart Posted onOctober 5, 2025October 6, 2025 22 Comments
Thai Airways Premium Economy Plus service

On Facebook, Thai Airways launched its new Premium Economy Plus class and it’s comparable to business class, but details are scant, and questions abound.  Thai Airways Premium Economy Plus In an announcement on Facebook, Thai Airways launched a new...

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Travel

California Insurance Chief’s Luxury Travel Sparks Probe

Kyle Stewart Posted onOctober 5, 2025October 4, 2025 23 Comments
California Insurance Chief Ricardo_Lara_Official_2015

California’s insurance chief allegedly billed taxpayers for luxury trips, business class, and security. Here’s what’s been discovered. Background: How A Travel Story Turned Political A viral post alleges that California’s Insurance Commissioner has been globe-trotting on the public dime....

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777Boeing

777X Delay: First Deliveries Now Penciled In for Early 2027

Kyle Stewart Posted onOctober 5, 2025October 4, 2025 6 Comments
777X 777-9

Bloomberg says Boeing’s 777X timeline slides again, with airlines and investors bracing for the ripple effects. Boeing’s Response To The Airbus A350 Delays Again Boeing’s 777X has been the big widebody bet for long-haul fleets looking for more range...

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American Express

Fed Up: Downgrading High Annual Fee American Express Cards

Kyle Stewart Posted onSeptember 28, 2025September 28, 2025 66 Comments
american express dual cards

After the latest hike in exchange for more coupons I don’t care about, I am fed up with American Express and its useless coupon card.  Fees Increase, Again As covered here, and virtually everywhere, American Express is again increasing...

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