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Kyle Stewart

1387 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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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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HawaiiHotel ReviewsHyatt

Review: Hyatt Centric Honolulu Disappoints

Kyle Stewart Posted onDecember 29, 2019September 13, 2021 32 Comments
Hyatt Centric Waikiki pool and sea view

I had a chance to try out the Hyatt Centric in Honolulu and my oh my, how disappointing it was. If you are considering booking travel or signing up for a new credit card please click here. Both support LiveAndLetsFly.com. If you...

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aadvantageAmerican AirlinesNews

American Airlines Shows Advantages of Eliminating Award Charts

Kyle Stewart Posted onDecember 22, 2019November 14, 2023 7 Comments
American Airlines Dog Lawsuit

American Airlines offered an outstanding deal in long haul first-class and great prices on business class fares. As much as we all want to hate airlines eliminating award charts, this example shows excellent advantages to doing so.  If you...

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AirbnbItalyNews

Airbnb Experiences: Making Pizza In Rome

Kyle Stewart Posted onDecember 22, 2019September 13, 2021 7 Comments
Lucy's finished product

During our recent trip to Rome, we decided to try out Airbnb Experiences following a recommendation from a friend. We learned how to make a pizza from a pro in Rome and it didn’t disappoint. If you are considering...

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HiltonHotel ReviewsHotels

Review: Aleph Rome Hotel – Curio by Hilton

Kyle Stewart Posted onDecember 22, 2019September 13, 2021 7 Comments
Junior Suite 200

Rome is filled with low-rise boutique hotels and Aleph Rome Hotel, now part of Hilton’s Curio collection is just one such boutique hotel delivering luxury to the Eternal City. If you are considering booking travel or signing up for a new...

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American Airlines

American Airlines Offers Differentiation For Frequent Flyers

Kyle Stewart Posted onDecember 15, 2019November 14, 2023 18 Comments
American Versus Delta Raises

American Airlines announced this week that they would allow frequent flyers to spend their way to frequent flyer status. I welcome this news and it’s different than what United offered. If you are considering booking travel or signing up for a...

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HyattNewsStarwood Preferred Guest

SPG Should Have Taken the Hyatt Offer

Kyle Stewart Posted onDecember 15, 2019September 13, 2021 55 Comments
The Living Room

Starwood Preferred Guest hotels sold to Marriott a couple of years ago. Now, following the first full year of their combined loyalty program, it’s clearer than ever – SPG should have taken Hyatt’s acquisition offer. If you are considering...

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Hotel ReviewsHyattParisPark Hyatt

Review: Park Hyatt Paris-Vendome – Suite

Kyle Stewart Posted onDecember 15, 2019September 13, 2021 7 Comments
Park Hyatt Paris-Vendome room service breakfast for three

A stay in Paris should be magic, and in our case it certainly was. The Park Hyatt Paris-Vendome delivered on a perfect Parisian stay.  If you are considering booking travel or signing up for a new credit card please click here. Both...

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NewsUnited Airlines

Unlike Matthew, United’s CEO Change Makes Me Reconsider Loyalty

Kyle Stewart Posted onDecember 8, 2019November 14, 2023 41 Comments
United CEO Scott Kirby

United announced this week that CEO, Oscar Munoz, would step down with United President, Scott Kirby, taking over May 1st, 2020. Changes like these don’t affect flyers often but I’m reconsidering my loyalty to United. If you are considering...

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Elite StatusNewsUnited Airlines

The Case For, Against Airline Loyalty

Kyle Stewart Posted onDecember 8, 2019November 14, 2023 14 Comments
United Airlines 2020 Leadership Change

Following unwanted management changes at United and unrequited management changes at American, I am re-examining my airline loyalty. Here are the arguments for and against holding loyalty status. If you are considering booking travel or signing up for a new credit...

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KimptonNews

Manchester’s Principal Hotel Rebranded Kimpton Clocktower

Kyle Stewart Posted onDecember 8, 2019September 13, 2021 2 Comments
Kimpton Clocktower lobby

We know Manchester (we lived there for several years) and love The Principal hotel. IHG acquired it (along with 13 others) last year in an effort to bolster the Kimpton brand. In January, the Kimpton Clocktower will launch where...

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Deals

Cyber Monday Travel Steals Still Available

Kyle Stewart Posted onDecember 2, 2019September 13, 2021 2 Comments
barclays credit card

It’s not too late to grab some Cyber Monday travel deals. Here are some deals you might want to grab for someone special or just for yourself.  If you are considering booking travel or signing up for a new credit card...

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