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Kyle Stewart

1489 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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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

A New Uber Scam And How To Avoid It

Kyle Stewart Posted onFebruary 1, 2026February 1, 2026 36 Comments
new uber scam

I came across a terrifying new Uber scam that had multiple components on a recent trip to Mexico. Some aspects incredibly inventive, others coincidental.  This is going to seem like an American Express ad by the end of the...

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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 18 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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JetBlue

JetBlue And JAL Split After A Partnership That Never Worked

Kyle Stewart Posted onJanuary 4, 2026January 4, 2026 4 Comments
JetBlue Airways Airbus A320s Boston

JetBlue’s Japan Airlines redemption partnership ends 3/31/26. It was underbuilt, under-marketed, and often showed phantom space. The Partnership That Arrived Quietly And Left Quietly JetBlue and Japan Airlines (JAL) are pulling the plug on their reciprocal points partnership on...

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Travel

With The US “Running” Venezuela, Travel Is Poised To Return

Kyle Stewart Posted onJanuary 4, 2026January 5, 2026 17 Comments
Venezuela Aviation Safety

President Donald Trump’s statement that the United States will “run the country” of Venezuela, travel will flood back, here is how and why.  US Captures Maduro and His Wife, What Now? In a night time raid that saw 150...

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Italy

Unpopular Opinion: Trevi Fountain’s New €2 Charge Is Right

Kyle Stewart Posted onJanuary 4, 2026 18 Comments
trevi fountain

Trevi Fountain in Rome implemented a €2/person charge and I think it’s the right approach but I am sure I will be burned at the stake for this unpopular opinion. Trevi Fountain Implements €2 Fee From February 1st, 2026...

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Lounge Reviews

American Airlines: Flagship Lounge Philadelphia Lags Others

Kyle Stewart Posted onDecember 28, 2025December 28, 2025 10 Comments
American Airlines Lounge Philadelphia flagship elevated seating

The introduction of American Airlines new Flagship lounge at Philadelphia is an utter disappointment and lags significantly behind the competition.  New Flagship Lounge Open In Terminal A the American Airlines lounges (Philadelphia) are open for business and on a...

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Travel

A Two-Star Hotel Stay at the World’s Biggest Luxury Conference

Kyle Stewart Posted onDecember 28, 2025December 27, 2025 18 Comments
Two Star Hotel Cannes France - bedroom wide

In the most conflicted possible experience, I found myself in a two-star hotel during the world’s largest luxury travel conference, ILTM Cannes. But why?  Why I Intentionally Booked A “Two-Star” Hotel Location, location, location. For this particular event, ironically...

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Spirit

Spirit’s Engine Deal Buys Time

Kyle Stewart Posted onDecember 28, 2025December 28, 2025 3 Comments
Spirit Airlines Airbus A320

Spirit’s new Pratt deal and $140M cash boost buy breathing room, but survival still hinges on running a tighter airline, not just signing smarter contracts. A Lifeline Arrives, Quietly Spirit Airlines has spent the better part of the last...

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