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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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Hyatt

Hyatt Completes Playa Resorts Acquisition, Deepens All-Inclusive Lead

Kyle Stewart Posted onJune 29, 2025June 28, 2025 14 Comments
Hyatt Ziva cancun

Last week, Hyatt quietly closed on its $2.6bn acquisition of the remaining stake in Playa Hotels & Resorts, a move that’s flown somewhat under the radar but has outsized implications for the luxury all-inclusive space. If you blinked, you...

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Travel

My Body And Health Keeps Changing My Travel Plans

Kyle Stewart Posted onJune 29, 2025June 29, 2025 24 Comments
kyle stewart family

For the second time in two weeks, my body has told me I need some time away, and it’s twice affected my travel plans.  Hospitalized, Stuck A couple of weeks ago I was in Florida and found a familiar...

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JetBlue

The JetBlue Mosaic Challenge And Why I Can’t Pass It Up

Kyle Stewart Posted onJune 22, 2025June 22, 2025 3 Comments
JetBlue Madrid

JetBlue is offering American Airlines Executive Platinum, Concierge Key and Delta Platinum, 360 members a status challenge I can’t say no to. Status Match, Challenge JetBlue has rolled out a status match for competing carriers to its markets. Significant...

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Southwest Airlines

Southwest’s (Possible) European Expansion Another Misstep

Kyle Stewart Posted onJune 22, 2025June 22, 2025 8 Comments
PLAY Airlines Iceland

Southwest Airlines has been rumored to have Iceland in its sites for European expansion of its network. Yet another misstep by its wayward management team. Southwest Airlines Rumored To Add Iceland To Its Map I’m not breaking any news...

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Travel

Tragic: Shocking Footage Of A Fatal Hot Air Balloon Accident

Kyle Stewart Posted onJune 22, 2025June 22, 2025 11 Comments
hot air balloon crash brazil

Footage flooded social media of a tragic hot air balloon accident in southern Brazil.  Shocking Footage Tragic and shocking footage from southern Brazil flooded X and various social media platforms of a hot air balloon accident. WARNING: Some of...

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aadvantageAmerican Airlines

American Airlines Makes Good On Loyalty Points Data Snafu

Kyle Stewart Posted onJune 8, 2025June 8, 2025 5 Comments
American Airlines Q1 2025

At the close of the earning year for 2024 American Airlines loyalty points and Aadvantage elite status, there was a snafu – but American has made up for it and then some.  What Happened I outlined a few weeks...

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Travel

Starwood Hotels Is Back, And It May Be Better Than Ever

Kyle Stewart Posted onJune 8, 2025June 8, 2025 16 Comments
1Hotel South Beach Miami

As of March 5, 2025, SH Hotels & Resorts has officially rebranded as Starwood Hotels, marking a significant return of the iconic brand under its original founder, Barry Sternlicht . The Return of a Hospitality Icon Barry Sternlicht, the...

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Hotels

The Worst Hotel Design Feature Is Everywhere

Kyle Stewart Posted onJune 8, 2025June 8, 2025 17 Comments
hotel bathroom barn door with closet open

Modern hotel design, especially in refurbished business hotels, have a common problem – a sliding barn door in the worst possible place.  Obvious Design Flaw Most hotel design features are intentional, use space and resources efficiently and make the...

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JetBlue

United-JetBlue Tie Up Leaves American Airlines Bloodied

Kyle Stewart Posted onJune 1, 2025June 1, 2025 12 Comments
JetBlue Madrid

In a move that has sent ripples through the aviation industry, United Airlines and JetBlue have announced a strategic partnership dubbed “Blue Sky.” This collaboration aims to enhance customer experience by integrating loyalty programs and expanding route networks, all...

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Travel

Flight Attendant Faces 25 Years, Allegedly Smuggled “Human Bone” Drug

Kyle Stewart Posted onJune 1, 2025June 1, 2025 21 Comments
flight attendant smuggler via Sri Lanka police

A former flight attendant was caught allegedly smuggling a significant quantity of a new drug made of human bone and now faces up to 25 years behind bars in Thailand.  In a case that has captured international attention, 21-year-old...

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Delta Air Lines

Delta’s Play In Orlando—New Focus City Strategy Emerging?

Kyle Stewart Posted onJune 1, 2025June 1, 2025 15 Comments
Delta orlando

Delta Air Lines just did something that, on the surface, looks small: seven new Saturday-only flights from Orlando. But the implications run much deeper. Come December 20, Delta will begin service from Orlando (MCO) to Birmingham (BHM), Cincinnati (CVG),...

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Hotels

Private Clubs Are The Latest Trend In Luxury Hotels

Kyle Stewart Posted onMay 25, 2025May 25, 2025 12 Comments
private member clubs

After meeting with more than 60 hoteliers over a three-day period at an invite-only event, the next big trend for luxury hotels doesn’t involve guests at all.  Private members’ clubs have long been the domain of the elite, offering...

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Travel

ANA Passenger Tried To “Murder All Onboard”, Diverts To Seattle

Kyle Stewart Posted onMay 25, 2025 4 Comments
a plane on the runway

On May 24, 2025, All Nippon Airways Flight NH114, en route from Tokyo Haneda to Houston, experienced a midair emergency when a passenger attempted to open an emergency exit door. Approximately nine hours into the flight, the individual, reportedly...

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HotelsHyatt

Sneak Peek At The Thompson Miami Beach (Opens Fall 2025)

Kyle Stewart Posted onMay 25, 2025June 11, 2025 5 Comments
Thompson Miami Beach courtesy of Hyatt Hotels-Two-Queen-Beds-With-Balcony

I was invited to a behind the scenes sneak peek at the glorious new Thompson Miami Beach, and it looks amazing – even under construction. Address: 1685 Washington Avenue, Miami Beach, FL 33139 Google Maps Link Under Construction In...

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Analysis

Spirit, Southwest, JetBlue: Time to Rethink Perceptions

Kyle Stewart Posted onMay 18, 2025May 19, 2025 8 Comments
United JetBlue Partnership

In just the last nine months, three carriers with distinct identities, Spirit, Southwest, and JetBlue have significantly shifted but public  perceptions might be harder to change.  We cling to airline stereotypes like old luggage—worn out, busted at the zippers,...

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Alaska Airlines

What Hawaiian Airlines AMEX Exit Means For Alaska MileagePlan

Kyle Stewart Posted onMay 18, 2025September 29, 2025 11 Comments
Alaska-Hawaiian Merger DOT

As Alaska Airlines and Hawaiian merge their loyalty programs, a final date has been provided for American Express Membership Rewards to Hawaiian Airlines (and thus, Alaska Airlines.) The writing has been on the hangar wall for a while now:...

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Travel

Global Airlines Defies Some Critics, Justifies Others

Kyle Stewart Posted onMay 18, 2025May 18, 2025 5 Comments
global airlines

Most critics thought Global Airlines would never get off the ground, but this week it proved most of the critics wrong – but not all.  In August 2023, I wrote about Global Airlines’ ambitious plan to break into the...

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Chase

Crazy Chase Sapphire Reserve Changes Floated

Kyle Stewart Posted onMay 11, 2025May 12, 2025 19 Comments
Chase Sapphire Lounge LGA

Some radical changes were floated online for the Chase Sapphire Reserve credit card. They are drastic and flatly: crazy. Higher Fee, More Coupons In a report from Doctor of Credit, Chase is following the lead of American Express and...

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Travel

A Deeper Dive Into Duffy’s Air Traffic Control Overhaul Plan

Kyle Stewart Posted onMay 11, 2025May 11, 2025 25 Comments
airport control tower atc duffy

Transportation Secretary Sean Duffy has announced an ambitious plan to modernize the United States’ air traffic control (ATC) system, let’s take a closer look. Duffy aiming to address decades of underinvestment and technological stagnation. The initiative, prompted by recent...

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Family Travel

Appreciation Of A Traveling Mother: My Wife

Kyle Stewart Posted onMay 11, 2025May 11, 2025 4 Comments
mothers day rome colisseum

Throughout the year, the evidence of my wife’s dedication to our children is evident, especially when we travel.  Always Sharing Her Seat When it comes to traveling as a family, especially with infants, it’s my wife that shares her...

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