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Kyle Stewart

1535 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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ChaseUnited Airlines

MileagePlus Changed the Game. Here’s What’s Really at Stake

Kyle Stewart Posted onFebruary 22, 2026February 22, 2026 17 Comments
United Airlines Boeing 787 at gate

United just restructured MileagePlus to punish non-cardholders. The bigger question is whether it will grow Chase card signups or push miles lovers elsewhere. United Airlines announced this week that MileagePlus is getting its biggest overhaul in more than a...

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rental cars

AI Rental Car Scans Produce Questionable Reports, Real Bills

Kyle Stewart Posted onFebruary 22, 2026February 21, 2026 11 Comments
hertz ai rental car damage scan​ via Proovstation

Hertz and Sixt are using AI scanners that automatically flag rental car damage. Customers are getting hit with surprise bills for marks no human eye can catch. If you have been on X this week, you may have already...

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Law In Travel

Tariffs Are Out: Will Foreign Travelers Come Back to the US?

Kyle Stewart Posted onFebruary 22, 2026February 21, 2026 25 Comments
Trump tariffs

The Supreme Court struck down Trump’s tariffs, but the US travel slump runs deeper than trade policy. Will the ruling actually change anything? Friday was a big day in American legal history. The Supreme Court ruled 6-3 in Learning...

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Travel

Book Club Retreats Are Turning Resorts Into Reading Nooks

Kyle Stewart Posted onFebruary 15, 2026February 15, 2026 8 Comments
reading retreats hemingway house key west

Book clubs are escaping the living room for resorts. From Moab “glamping” to literary tours, reading is becoming a legitimate motivation to travel. Book Clubs Have Left The Living Room And Headed To The Resort An interesting new trend...

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Travel

Cannes to Monaco Day Trip: How to Get There by Train

Kyle Stewart Posted onFebruary 15, 2026May 16, 2026 12 Comments
Monte Carlo Monaco marina view

A day trip from Cannes to Monaco by train costs about €12, takes 63 minutes, and is one of the best side trips on the French Riviera.

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Travel

LA’s “Hottest” Coffee Shop Is Found Inside Someone’s Home

Kyle Stewart Posted onFebruary 15, 2026February 15, 2026 4 Comments
MEHKO coffee shop grenada echo park

A viral LA coffee counter runs from a private home, and it raises big questions about safety, access, and whether this model can travel. Los Angeles has never been shy about eating (or drinking) in unconventional places. Taco trucks...

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Rail Travel

Halloway Bets Big On Private Rail Travel In America, Again?!

Kyle Stewart Posted onFebruary 8, 2026February 8, 2026 12 Comments
halloway american premium rail

Halloway is putting private railcars onto Amtrak, with chef-driven luxury and high design. Welcome to the new era of great American rail vacations.  The Return Of Slow Travel, With A Very American Twist For decades, Americans have treated trains...

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Travel

Hotels: Wellness Is Out, Longevity Is The New Affluent Draw

Kyle Stewart Posted onFebruary 8, 2026February 8, 2026 9 Comments
Amangati Spa - courtesy of Aman at Sea

Juice bars are passé. Ultra-luxury hotels sell longevity with diagnostics, IV drips, and biohacking, and the price tags prove it. Wellness Was The Warm-Up For the last decade, “wellness” in high-end hospitality has been a pretty predictable script: a...

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Frontier

Frontier Airlines Super Bowl Deal Turns Old Miles Into Flights

Kyle Stewart Posted onFebruary 8, 2026February 8, 2026 5 Comments
frontier miles

Pepsi Points never delivered a jet. Frontier just did, with a Super Bowl-season promo that turns forgotten points into a headline-grabbing redemption story. Frontier Airlines just pulled off one of the most entertaining airline promotions in years: it “redeemed”...

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ChaseCredit Cards

The Chase Dining Perk Is Incredible… Where It’s Available

Kyle Stewart Posted onFebruary 1, 2026February 2, 2026 18 Comments
Chase dining benefit - Oise Ristorante

Climbing credit card annual fees place extra emphasis on the value of its benefits. The Chase Dining credit, but it’s my favorite now – when it’s available.  In a prior version, this post contained an error that American Express...

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Uber

New Uber Scam: What It Looks Like and How to Avoid It

Kyle Stewart Posted onFebruary 1, 2026May 16, 2026 37 Comments
new uber scam

I fell for a sophisticated new Uber scam in Cancun, Mexico. Here is how it works, why it is so effective, and how to protect yourself.

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American Airlines

American’s 2025 Earnings Look Awful Next To Delta And United

Kyle Stewart Posted onFebruary 1, 2026February 1, 2026 11 Comments
American Airlines Boeing 777-200 parked

Record revenue, relatively insignificant profit: American earned $111M on $54.6B while Delta and United cleared billions. The gap is getting hard to ignore. Record Revenue, Familiar Disappointment American Airlines just posted record full-year 2025 revenue of $54.6 billion, yet...

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TravelVenezuela

Laser Airlines Seeks Caracas-Miami Flights, Twice Daily Now

Kyle Stewart Posted onJanuary 25, 2026 1 Comment
flights to venezuela

A Venezuelan carrier wants Caracas-Miami service on MD-80s or a 767. Here’s why demand exists, and why US approval is still a long shot. Laser Airlines Files For Flights To The US A filing circulating in aviation circles shows...

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News

Will January 25, 2026 Be The Worst US Flight Day Ever?

Kyle Stewart Posted onJanuary 25, 2026January 25, 2026 13 Comments
flight cancellations snow airport

Storms, ATC constraints, and airline ops collide. But does January 25, 2026 truly belong in the “worst day ever” conversation? Airlines Cancel Flights En Masse For most major hubs, flights cancelled for Sunday January 25th, 2026 at an historically...

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Boeing

Surprisingly, Boeing Is On A Sales Tear, Especially In The Widebody Market

Kyle Stewart Posted onJanuary 18, 2026January 18, 2026 12 Comments
Boeing 2025 sales

In a surprising shift, Boeing has had an incredibly strong year despite significant, persistent, aircraft approval delays. Airbus is losing on widebodies. For the better part of a decade, the commercial aircraft sales narrative has been painfully predictable. Airbus...

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Ryanair

Why Elon Musk Should Buy Ryanair

Kyle Stewart Posted onJanuary 18, 2026January 18, 2026 19 Comments
elon musk ryan air michael oleary starlink

If Elon Musk were to seriously consider buying a major airline, Ryanair might not be the fantastical choice critics would expect. The Irish ultra-low-cost carrier isn’t just cheap on ticket prices; it’s one of the most profitable and operationally...

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Frontier

Frontier Stops Selling Flights After April 13, 2026

Kyle Stewart Posted onJanuary 18, 2026January 18, 2026 5 Comments
frontier stops selling flights

Frontier’s booking calendar stops at April 13, 2026. That’s unusual, and it lands right as the ULCC world gets very, very interesting. Frontier’s Schedule Stops On April 13, 2026, Just 85 Days Away If you are trying to book...

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Elite Status

I Tried Status-Free Airline, Hotel Free Agency And Hated It

Kyle Stewart Posted onJanuary 11, 2026January 29, 2026 13 Comments
American Airlines Boeing 787-9 Premium Business Class seat

After years of frustration with loyalty programs I proudly freed myself of the elite status grind. I hated it and came crawling back to both airline and hotel status.  Why Chasing Status Had Run Its Course Every year the...

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HyattMarriott

Mocked For Hyatt–Rosewood Take, Now Marriott Circles

Kyle Stewart Posted onJanuary 11, 2026January 11, 2026 11 Comments
Rosewood Baha Mar lobby marriott

I was roasted for suggesting Rosewood should sell to Hyatt. Now leaked documents point to a Marriott-Rosewood tie-up. [Alleged] Marriott Legal Email Screenshot Leaks Rosewood Acquisition Plans Over the past few days a rumor has been making the rounds...

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Aer Lingus

Aer Lingus Is Pulling Long-Haul Out Of Manchester

Kyle Stewart Posted onJanuary 11, 2026January 11, 2026 16 Comments
Aer Lingus A321neo

If you were hoping Aer Lingus’ base in Manchester would help claw back long-haul relevance, you may want to sit down. Aer Lingus is set to stop selling long-haul flights from Manchester beyond March 31, 2026, specifically the Manchester...

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