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Kyle Stewart

1475 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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Uber

Uber And Lyft Need To Solve Pickup Time Management

Kyle Stewart Posted onFebruary 4, 2024February 3, 2024 47 Comments
uber Lyft

Uber and Lyft have seemingly abandoned all efforts to provide an accurate pickup time.  If you are considering booking travel or signing up for a new credit card please click here. Both support LiveAndLetsFly.com. If you haven’t followed us on Facebook or Instagram, add us today. My...

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Hotel Reviews

Review: Hilton Miami Downtown

Kyle Stewart Posted onFebruary 4, 2024February 4, 2024 6 Comments
Hilton Miami Downtown room with seat

The Hilton Miami Downtown is everything that a classic business hotel should be, and that applies to both the good and bad elements.  If you are considering booking travel or signing up for a new credit card please click here. Both support LiveAndLetsFly.com. If...

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Travel

Falling In Love With Puerto Rico

Kyle Stewart Posted onJanuary 28, 2024January 28, 2024 11 Comments
puerto rico san juan cobblestone

Our first trip to Puerto Rico was brief but enlightening. Not only did we fall in love with the island, but we might just move there… might.  If you are considering booking travel or signing up for a new credit card please click...

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Travel

Wall Street Journal Ranks Delta Best, JetBlue Worst In 2023

Kyle Stewart Posted onJanuary 28, 2024January 28, 2024 13 Comments
Wall Street journal annual airline rankings

The Wall Street Journal’s annual airline rankings are in with Delta Air Lines at the top and JetBlue Airways at the bottom for the third straight year.  If you are considering booking travel or signing up for a new credit card please click...

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Cruise

First Look: Icon Of The Seas, World’s Largest Cruise Ship

Kyle Stewart Posted onJanuary 28, 2024March 14, 2024 23 Comments
Icon of the seas iconic size

My travel agency was invited to get a first look at Royal Caribbean’s Icon of The Seas, the world’s largest cruise ship. 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 Reviews

Review: Hilton Barbados Resort

Kyle Stewart Posted onJanuary 21, 2024 11 Comments
hilton barbados resort pools

To close out our amazing trip aboard Explora Journeys, we spent two days in Barbados at the Hilton and wish we had just flown straight home.  If you are considering booking travel or signing up for a new credit card please...

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JetBlue

Broad Implications: Court Ruling Bigger Than JetBlue-Spirit Merger

Kyle Stewart Posted onJanuary 21, 2024January 21, 2024 4 Comments
jetblue spirit merger

A recent ruling to block JetBlue’s acquisition of Spirit Airlines could have broad implications for not only both carriers but the US airline market.  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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Travel

It’s Been A Rough Start In 2024 For Commercial Aviation

Kyle Stewart Posted onJanuary 21, 2024January 21, 2024 17 Comments
scott kirby

Just three weeks into 2024, and already it’s been a very rough start for commercial aviation, specifically in the United States.  If you are considering booking travel or signing up for a new credit card please click here. Both support LiveAndLetsFly.com. If...

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JetBlue

Breaking: Judge Blocks JetBlue-Spirit Merger

Kyle Stewart Posted onJanuary 16, 2024January 16, 2024 20 Comments
jetblue spirit merger

A federal judge ruled on JetBlue’s attempt to purchase Spirit Airlines today, January 16th, 2024.  If you are considering booking travel or signing up for a new credit card please click here. Both support LiveAndLetsFly.com. If you haven’t followed us on Facebook...

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CruiseExplora JourneysFamily Travel

Trip Report: Explora Journeys Castries, St. Lucia

Kyle Stewart Posted onJanuary 14, 2024January 14, 2024 1 Comment
explora journeys st lucia Vigie beach tai chi

The last stop on our all-luxury Explora Journeys cruise was Castries, St. Lucia and we finally found our rhythm.  If you are considering booking travel or signing up for a new credit card please click here. Both support LiveAndLetsFly.com. If you haven’t...

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JetBlue

Robin Hayes’ JetBlue Exit Leaves More Questions Than Answers

Kyle Stewart Posted onJanuary 14, 2024January 14, 2024 6 Comments
JetBlue Robin Hayes Spirit Airlines Merger

Robin Hayes, JetBlue CEO, announced his resignation from the carrier. But the timing and transition leaves more questions than answers. 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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CruiseExplora JourneysFamily Travel

Trip Report: Explora Journeys Guadeloupe (Skipped) And St. Barth’s

Kyle Stewart Posted onJanuary 14, 2024January 14, 2024 2 Comments
Explora Journeys St Barths french caribbean heaven

The next stops on our all-luxury Explora Journeys cruise were Deshaies, Guadeloupe, Gustavia, St. Barth’s kept us in an ocean state of mind.  If you are considering booking travel or signing up for a new credit card please click here. Both support...

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aadvantage

Comprehensive Guide: American Airlines Elite Status in 2024

Kyle Stewart Posted onJanuary 7, 2024January 7, 2024 19 Comments
American Airlines status

A comprehensive guide to American Airlines Status, including an overview of the AAdvantage loyalty program, understanding the different levels and benefits of elite status, earning Loyalty Points, maximizing the value of elite status, and tips for achieving and maximizing...

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Safety

Reasonable Question: Is The 737 Max Safe?

Kyle Stewart Posted onJanuary 7, 2024January 7, 2024 51 Comments
Alaska Airlines 737-9 MAX

Following yet another incident, most recently on Friday night, reasonable questions about one of Boeing’s most controversial planes are being asked: Is the 737 MAX safe?  If you are considering booking travel or signing up for a new credit card please...

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Explora JourneysFamily Travel

Trip Report: Explora Journeys St. John’s Antigua And Barbuda

Kyle Stewart Posted onJanuary 7, 2024January 7, 2024 1 Comment
st johns antigua sandy beach and chairs

The next stop on our all-luxury Explora Journeys cruise was St. Johns, Antigua and Barbuda. We kept it simple and inexpensive enjoying an incredible beach.  If you are considering booking travel or signing up for a new credit card please click...

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Explora Journeys

Trip Report: Explora Journeys Sea Days And Spanish Town (British Virgin Islands)

Kyle Stewart Posted onDecember 31, 2023December 31, 2023 3 Comments
Explora Journeys tender

Sea days are seen as boring by some, but they were our favorite on our Butterfly Islands trip with Explora Journeys and we had an interesting time at Spanish Town too.  If you are considering booking travel or signing up for...

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Year in Review

2023 In Review: Status, Destinations, Predictions Dashed

Kyle Stewart Posted onDecember 31, 2023December 31, 2023 4 Comments
Explora Journeys st barths

After a wild year, here’s where things ended up for me and my family, my predictions, and a look ahead. 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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Travel

Video: Man Restrained By Passengers And Crew On Miami Flight

Kyle Stewart Posted onDecember 31, 2023December 31, 2023 8 Comments
Miami passenger restrained

A serious incident took place onboard an American Airlines flight to Miami from Rio on Saturday morning resulting in passengers and crew restraining a man.  If you are considering booking travel or signing up for a new credit card please click...

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Explora JourneysFamily TravelTrip Reports

Trip Report: Explora Journeys Cruise – Key West

Kyle Stewart Posted onDecember 24, 2023December 24, 2023 5 Comments
Kimpton Key West pool

As part of our trip throughout the Caribbean, we spent ten days onboard Explora Journeys and it was an all-inclusive five-star resort at sea. The first port of call was Key West, Florida.  If you are considering booking travel or signing...

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Upgrades

It’s The Giving Season… For Upgrades And Extras

Kyle Stewart Posted onDecember 24, 2023December 24, 2023 34 Comments
United Polaris cabin Washington Dulles Paris

As we close the year, we are reminded to give especially in the case of expiring upgrades, instruments, and extras we may not be able to use ourselves.  If you are considering booking travel or signing up for a new credit...

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