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Kyle Stewart

1378 Articles

Pittsburgh, PA
Kyle is a freelance travel writer with contributions to Time, the Washington Post, MSNBC, Yahoo!, Reuters, Huffington Post, MapHappy, 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 and daughter. Email: sherpa@thetripsherpa.com
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Global EntryNew YorkNews

DHS Was Right To Block New York Global Entry Applicants

Kyle Stewart Posted onFebruary 9, 2020September 13, 2021 98 Comments
blocked security

The Department of Homeland Security began blocking New York residents from applying for their trusted traveller program, Global Entry, over the state’s “Sanctuary policies” but there’s more to the story and DHS was right to do it.  If you...

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NewsUnited Airlines

United App Unnecessarily Forces Update, Frustration

Kyle Stewart Posted onFebruary 9, 2020September 13, 2021 8 Comments
United Proactive Compensation

The Coronavirus has caused a number of shifts in air travel, but United forced users to update their app. Flyers had issues at the airport, but other airlines didn’t require the same. If you are considering booking travel or signing up...

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HotelsHyatt

Pirates of the Caribbean: Grand Hyatt Baha Mar

Kyle Stewart Posted onFebruary 9, 2020September 13, 2021 19 Comments
Mostly empty

We got in on an incredible hotel suite deal, but food and beverage of the $4.2bn Grand Hyatt Baha Mar resort are the true Pirates of the Caribbean.  If you are considering booking travel or signing up for a new credit...

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American AirlineschinaDelta Air LinesNewsUnited Airlines

Airlines Use Coronavirus As Excuse To Reduce Losses, Save Face

Kyle Stewart Posted onFebruary 2, 2020September 13, 2021 18 Comments
China Flight Suspension

The airline business is tricky, but some carriers see opportunity in the Coronavirus to reduce their losses and save face when routes haven’t gone as planned.  If you are considering booking travel or signing up for a new credit card please...

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DisneyNews

Disney Parks are Expensive, Make Less Than You’d Think

Kyle Stewart Posted onFebruary 2, 2020September 13, 2021 19 Comments
Pandora at Disney's Animal Kingdom

As a new Disney Annual Passholder, I am amazed by how much goes into the parks and how many people visit. I looked into the business and was surprised that they don’t make more money. If you are considering...

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HiltonHilton HHonorsHotel ReviewsHotels

Review: Hilton Orlando Buena Vista Palace

Kyle Stewart Posted onFebruary 2, 2020September 13, 2021 6 Comments
Hilton Buena Vista Palace

With our new Disney Annual Passes, we find ourselves in Orlando but keep searching out the best value for money in the area. Previously, we loved Hilton Bonnet Creek and our daughter favored the bi-level suite at Hyatt Grand...

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Delta Air LinesDelta SkyMilesNews

Editorial: Delta Is Living In The Future

Kyle Stewart Posted onJanuary 26, 2020September 13, 2021 22 Comments
Delta Free Wi-Fi

Delta has become the airline to beat in many respects among US carriers. From pet carriers to closed-door business class suites, Delta is absolutely living in the future. If you are considering booking travel or signing up for a new credit...

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American AirlinesNews

Like Impeachment, American Airlines CEO’s Removal May Have Consequences

Kyle Stewart Posted onJanuary 26, 2020September 13, 2021 35 Comments
American Airlines 737 MAX Lavatory

President Trump’s impeachment and potential removal from office could have consequences beyond the immediate result. Likewise, American Airlines CEO Doug Parker’s removal may have a lasting effect.  If you are considering booking travel or signing up for a new credit card...

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Disney

Adding Disney World’s Annual Pass to Our Lives

Kyle Stewart Posted onJanuary 26, 2020September 13, 2021 2 Comments
Disney's Galaxy's Edge

For Christmas this year we got a gift for the whole family, an Annual Passholder membership to Disney World (Florida.) Here is the low down on what pushed us over the edge.  If you are considering booking travel or signing up...

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American AirlinesNews

American Airlines Hasn’t Resolved Labor Issues

Kyle Stewart Posted onJanuary 19, 2020November 14, 2023 5 Comments
a man and woman smiling for a picture

The summer from hell has passed for American Airlines. Despite no announcements of any deals with their unions, all seems calm among labor groups at the world’s largest carrier, but that’s deceiving. If you are considering booking travel or signing up...

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Mileage PlusMileage RunsNewsUnited Airlines

This Trip Demonstrates Benefit of New United Airlines Mileage Plus Program

Kyle Stewart Posted onJanuary 19, 2020September 13, 2021 30 Comments
United Airlines Hong Kong Impairment

A fare deal came out this week that clearly demonstrates the benefits of the new United Mileage Plus program, one that should encourage those who might struggle to achieve $18,000 in spending annually.  If you are considering booking travel or signing...

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Hotel Reviews

Review: Hotel Contessa San Antonio – Suite

Kyle Stewart Posted onJanuary 19, 2020September 13, 2021 10 Comments
Hotel Contessa Living Room

On my very first trip to San Antonio, Texas this week I stayed at the Hotel Contessa and I was impressed with their suites.  If you are considering booking travel or signing up for a new credit card please click here. Both...

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American Expressamex platinumNewsSpirit

Why I Made Spirit Airlines my American Express Platinum Preferred Airline

Kyle Stewart Posted onJanuary 12, 2020September 13, 2021 11 Comments
a yellow airplane on a runway

American Express Platinum cardholders receive a $200 annual credit applied to offset fees charged by airlines. Almost no one chooses Spirit, here’s why I did.  If you are considering booking travel or signing up for a new credit card please click...

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HertzNational Car RentalNewsrental cars

Car Rental Agencies Don’t Offer Lifetime Status But Should

Kyle Stewart Posted onJanuary 12, 2020November 14, 2023 6 Comments
Maserati from National

Airlines and hotel chains offer lifetime elite status in their program for their most loyal customers, yet rental car agencies don’t. Why? If you are considering booking travel or signing up for a new credit card please click here. Both support LiveAndLetsFly.com....

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Hotel ReviewsHyatt

Review: Hyatt Regency Grand Cypress Orlando (Bi-Level Suite)

Kyle Stewart Posted onJanuary 12, 2020September 13, 2021 3 Comments
Hyatt Regency Grand Cypress from beach

Orlando is flush with hotels but after trying a few out, the Hyatt Regency Grand Cypress is among the most impressive. We were upgraded to a bi-level suite and it was extraordinary.  If you are considering booking travel or signing up...

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NewsSpirit

Is Spirit Airlines Breaking the Law With Passenger Usage Fee?

Kyle Stewart Posted onJanuary 5, 2020September 13, 2021 62 Comments
spirit bankruptcy

One of my favorite flight hacks is to buy Spirit Airlines tickets at the airport and save the online-only passenger usage fee. But based on a recent experience, it seems they may be breaking the law through false advertising...

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HyattUnited AirlinesUpgrades

Spend Your Upgrades Early and Often

Kyle Stewart Posted onJanuary 5, 2020November 14, 2023 1 Comment
Park Hyatt Paris-Vendome

Hotels, airlines and even car rental companies give us benefits that are good all year, but sometimes we treat them too preciously. This is the year to spend your upgrades early and often! If you are considering booking travel or signing...

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Loyalty Programs

Loyalty in 2019, Plan For 2020

Kyle Stewart Posted onJanuary 5, 2020September 13, 2021 Leave a Comment
United Washington Dulles Expansion

At the turn of the year (and in this case, the turn of the decade) reflection is important before forging ahead. My loyalty experience in 2019 was interesting, 2020 feels more intentional already. If you are considering booking travel or signing...

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Mileage PlusNewsUnited AirlinesUpgrades

United PlusPoints Bring Old Problems to New Situations

Kyle Stewart Posted onDecember 29, 2019November 14, 2023 14 Comments
a table with a laptop on it

United’s new PlusPoints has some benefits to travellers adding flexibility. However, old problems with United’s Global and Regional Premier Upgrades carry over to new situations.  If you are considering booking travel or signing up for a new credit card please click...

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NewsUber

Riders, Drivers Pay For Uber’s Bad Tech

Kyle Stewart Posted onDecember 29, 2019September 13, 2021 41 Comments
Uber Washington DC Tricks

Uber has several technical issues that cause issues for riders and drivers. These cost both sides of the equation money yet Uber hasn’t or won’t fix the app.  If you are considering booking travel or signing up for a new credit...

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