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Kyle Stewart

1384 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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Hyatt

Hypocrisy: Why I’m Doubling Down on Hyatt

Kyle Stewart Posted onJuly 29, 2018September 15, 2021 15 Comments
Shanghai Hyatts

Despite my bitterness toward Hyatt, reviewing my actual results for the year I decided to return to the brand full force and double down. Oh, the hypocrisy. If you are considering booking travel or signing up for a new credit card...

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Elite Status

Mid-Year Status Update – Surprising Results

Kyle Stewart Posted onJuly 22, 2018September 15, 2021 7 Comments
United A320

For the first time since I became a serious frequent flyer, I am carefully tracking all of my traveling metrics for elite status. Every flight and hotel stay is logged and I am sharing my results – my expectations didn’t...

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Luggage

Away Travel Replaces Smart Luggage Batteries

Kyle Stewart Posted onJuly 22, 2018September 15, 2021 5 Comments
Away battery replacement

Away Travel is offering a trade-out program for their previous generation bags in a move that is smart and helpful. Customers who previously purchased a piece of luggage from Away Travel can swap out their now out-of-compliance styles for...

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LuggageReviews

Luggage Review: Wool & Oak Duffle Bag

Kyle Stewart Posted onJuly 22, 2018September 15, 2021 6 Comments
Wool & Oak Duffle

For several years I have been traveling a mix of short road trips and some longer journeys domestically and abroad. For shorter trips, I prefer to simplify my packing and bring as little as possible. The Wool & Oak...

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Amazon

Amazon Prime Day: Kyle’s Traveler Picks

Kyle Stewart Posted onJuly 16, 2018September 15, 2021 1 Comment
Amazon Kindle

Amazon holds their Prime Day once per year which offers Black Friday-level discounts on participating products. I wanted to share my picks for travelers from the offerings. This year Amazon Prime Day has been extended, starting at 3PM Eastern...

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ClearPriority Pass

CLEAR Should Follow Priority Pass’ Lead

Kyle Stewart Posted onJuly 15, 2018September 15, 2021 11 Comments
Airport Lounge

CLEAR is a membership service that vets members to provide expedited security lines at airports and event centers. They have had limited growth, but if they followed the lead of lounge membership company, Priority Pass, perhaps they could scale...

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Travel

Review: Tru Hotel Pigeon Forge – Patronizing Millennials

Kyle Stewart Posted onJuly 15, 2018September 15, 2021 26 Comments
Tru Hotel

Tru is a new hotel brand by Hilton focused on a younger generation. The select service property (this location in Pigeon Forge, Tennessee) trades design elements for cramped conditions. Does it work or is it patronizing (hint: patronizing)? If...

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Hotel Reviews

Review: DoubleTree Colorado Springs – Presidential Suite

Kyle Stewart Posted onJuly 15, 2018September 15, 2021 3 Comments
Doubletree Colorado Springs

The DoubleTree Colorado Springs is a massive hotel with conference center. I was pleasantly upgraded to the Presidential Suite due to my status with Hilton and couldn’t be happier with the product I received. If you are considering booking...

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Hyatt

Hyatt Knows They Went Too Far With Globalist Requirements

Kyle Stewart Posted onJuly 8, 2018September 15, 2021 28 Comments
Park Hyatt Sanya

Hyatt changed their loyalty program, Gold Passport to World of Hyatt, increasing their requirements for Globalists (top-tier elites) as much as 140%. They went too far and now their actions demonstrate that they know it. But is it a case...

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Travel

Must-Have Tools For Any Road Warrior

Kyle Stewart Posted onJuly 8, 2018September 15, 2021 16 Comments
road warrior

Like many of our readers, I am a full-time road warrior at this point in my career. Readers, friends, and co-workers often ask me what tools I use to make life easier. Here are my must-have tools for any...

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Iberia

My Avios Have Arrived And I Can’t Spend Them Fast Enough

Kyle Stewart Posted onJuly 3, 2018November 14, 2023 14 Comments
a plane on the runway

Iberia ran a promotion a couple of weeks ago with limited terms that many travelers took advantage of. After $340 and an hour of bliss with their excellent website, the Avios have arrived much to the dismay of many....

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American AirlinesIberia

Why We Are Spending Our Iberia Avios on Coach American Awards

Kyle Stewart Posted onJuly 1, 2018November 14, 2023 16 Comments
a plane flying in the sky

A recent, limited time promotion from Iberia effectively sold Iberia Avios for fractions of a penny each up to 90,000 in total. While many are using their points to fly in business class to Europe, we have opted for...

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Airbnb

All The Hotel Points In The World Can’t Beat This Airbnb

Kyle Stewart Posted onJuly 1, 2018September 15, 2021 5 Comments
airbnb damage

We fell in love with Mérida, Mexico before we even landed. With several million hotel points we could have had our pick from just about anywhere, so why did we spend money on an Airbnb when we could have...

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Airbnb

Proposals For An Airbnb Loyalty Program

Kyle Stewart Posted onJune 24, 2018September 15, 2021 5 Comments
Airbnb, Mexico

After reviewing some Airbnb properties and staying in one recently, it became evident that an Airbnb loyalty program is needed, not just for guests, but for their hosts as well. If you are considering booking travel or signing up for a...

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Hotel ReviewsHyatt

Review: Enormous Presidential Suite at the Hyatt Regency Coral Gables (Miami)

Kyle Stewart Posted onJune 24, 2018November 14, 2023 8 Comments
Miami Beach

When the absurd, ridiculous, opulent Presidential Suite at the Hyatt Regency Coral Gables (Miami) popped up for a bargain price, my family had to try it out. Two-floors, two bathrooms, huge views, all for less than we usually pay...

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Iberia

Iberia’s Website Is Down – No Surprise

Kyle Stewart Posted onJune 23, 2018September 15, 2021 19 Comments
Iberia A319

  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. UPDATE: It Appears the website is working again for...

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HiltonHilton HHonorsHotel Reviews

A Tale of Two Waldorf-Astoria Hotels

Kyle Stewart Posted onJune 17, 2018September 15, 2021 20 Comments
The Reach

We tried a pair of Waldorf-Astoria Key West properties and the two couldn’t have been more different. One had great grounds but terrible rooms, the other excellent rooms but none of the history. It was the most bizarre tale...

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Hotel ReviewsHotels

I Challenge You To Identify This Hotel Brand

Kyle Stewart Posted onJune 17, 2018September 15, 2021 34 Comments

We stayed at a hotel that was so far off brand that we checked out before our luggage arrived from the bell staff. Without cheating, can you identify this bad hotel room’s brand?  If you are considering booking travel or signing...

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North Korea

Would You Visit North Korea?

Kyle Stewart Posted onJune 10, 2018September 15, 2021 36 Comments
DPRK

As North Korea and the US sit down for talks in Singapore this week, I found myself wondering if it would be possible to visit under normal circumstances in the future, and if so, would I go? If you...

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Hot DealsTravel

Exchanging Free Business Class For Paid

Kyle Stewart Posted onJune 10, 2018November 14, 2023 8 Comments
a plane flying in the sky

Though we already had our Christmas tickets purchased, a change in the plans thanks to Hotwire.com had us swap in our “free” (paid with miles) tickets for reasonably-priced business class tickets.  If you are considering booking travel or signing up for...

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