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Kyle Stewart

1526 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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Bilt Buys Sion for $30M and It’s About the Data

Kyle Stewart Posted onMarch 22, 2026March 22, 2026 5 Comments
Bilt-Sion acquisition

Bilt acquired travel commission platform Sion for $30M. The price tag hints this is about transaction data, not travel concierge services.

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aadvantageAmerican Airlines

American Airlines Upgrade Offer Clever, Effective, Valuable

Kyle Stewart Posted onMarch 22, 2026March 22, 2026 6 Comments
an airplane with a television set

American Airlines offered Platinum Pro and Executive Platinum clients a rare opportunity to confirm upgrade space this week. It was clever, effective, and valuable.  American Airlines Offers A Limited Upgrade Option For New Bookings I was delighted to receive...

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Hotels

Churchill’s War Office Is Now a $1,000/Night Hotel

Kyle Stewart Posted onMarch 15, 2026March 15, 2026 10 Comments
raffles-london-churchill-lounge-bar

Churchill’s Old War Office is now Raffles London at The OWO, possibly the most historically significant luxury hotel in the world. Inside London’s Most Storied New Hotel There’s an incredible opportunit to stay in a building that shaped the...

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Travel

Virtuoso Survey: Partners Are Bullish On 2026

Kyle Stewart Posted onMarch 15, 2026March 15, 2026 4 Comments
virtuoso trends 2025 2026

Virtuoso's latest pulse survey shows travel suppliers and advisors heading into 2026 with rising confidence, strong pipelines, and only 3% pessimism on the partner side.

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Travel

Net Migration Is Negative, But Read The Fine Print

Kyle Stewart Posted onMarch 15, 2026March 15, 2026 13 Comments
Big Ben in London 2008

Headlines say Americans are fleeing in droves. The actual numbers tell a far more nuanced story about who is really leaving and why.

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Spirit

Spirit Has a Bankruptcy Plan But Fuel Prices Threaten It All

Kyle Stewart Posted onMarch 8, 2026March 8, 2026 12 Comments
Spirit Airlines Airbus A320 Boston

Spirit’s bankruptcy exit plan cuts debt by billions and shrinks to 94 planes. But surging fuel prices from the Iran conflict could derail the whole thing. Spirit Airlines has been through a lot. Two bankruptcy filings in under a...

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Travel

The 737 MAX Wants To Cross The Atlantic, And It May Just Win

Kyle Stewart Posted onMarch 8, 2026March 8, 2026 21 Comments
737 transatlantic

Airbus pioneered thin transatlantic routes with the A321 family, but 737s are muscling in with WestJet, Alaska, Southwest, and United. Is this real competition? The idea of flying a single-aisle jet across the Atlantic used to sound like a...

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Venezuela

US And Venezuela Just Normalized Relations. Now What?

Kyle Stewart Posted onMarch 8, 2026March 8, 2026 7 Comments
caracas-venezuela-credit-bona-lee

The US and Venezuela have restored full diplomatic ties for the first time since 2019. Flights are back. But the State Department still says don't go.

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Family TravelHotel ReviewsHotelsHyattNew York

Review: Hotel Seville Nomad (Queen Deluxe Room)

Kyle Stewart Posted onMarch 1, 2026March 1, 2026 2 Comments
hotel-seville-nomad-lobby-bar-2

The Hotel Seville Nomad, The Unbound Collection by Hyatt, sits in the heart of New York City’s NoMad neighborhood, one of the most walkable and vibrant districts in Manhattan.  Location The hotel is tucked along a quiet stretch of...

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Hyatt

Unpopular Opinion: I’m Not Outraged By Hyatt Award Increases

Kyle Stewart Posted onMarch 1, 2026March 1, 2026 11 Comments
Hyatt Hotel Martinez Cannes France sea view sunset

Hyatt Hotels increased the cost of award redemptions and while most of the miles and points community is outraged, I’m really not bothered but for practical reasons. Award Changes The headlines in the miles and points community this week...

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Travel

A Runner Did a 5K in an Airplane Bathroom. Why?

Kyle Stewart Posted onMarch 1, 2026March 1, 2026 12 Comments
airplane 5k

A marathoner locked himself in a plane lavatory for an hour to log a 5K on Strava. Passengers and the internet had thoughts.

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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

Day Trip: Cannes (Nice) To Monaco

Kyle Stewart Posted onFebruary 15, 2026March 1, 2026 12 Comments
Monte Carlo Monaco marina view

With an extra day after a conference I decided to travel from Nice to Monaco for the day. It was a perfect exploration.  I was in Nice, France for the International Luxury Travel Market, the world’s largest travel trade...

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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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