Welcome to the Inside the Upgrade newsletter, where I share specific strategies for booking luxury flights and hotels for a discount, exclusive newsletter travel tips I wish I knew sooner, and the latest destination guides so you can make the most of every trip.

I keep my email cadence light, I only ever send content I would personally want to receive ✈️🥂

Hey Reader,

I'm trying something new today to help people find business-class flights!

I've been having some fun using AI to build travel tools (like this TSA wait time calculator) so I've also built one to scan for business class flights under $2k round trip.

I'll show you the deals and the direct link on Google flights to book yourself (you don't have to go through me!) so I'm curious if people are interested. If you like it, I'll add it as a regular part of my newsletter. If you don't, I'll toss it out! The whole point of this community is to share travel deals and tips you find valuable, so that's what I focus on 😘

Check it out below and let me know if you're interested! Feel free to reply directly (I mean it!) if you have any other feedback as well.

Cheers,
Deryn

👉 Save 15% or more on hotel deals here​

I went looking for business class fares under $2,000, round-trip, for at least a week and Boston came through.

The standout is Azores Airlines, with a bunch of sub-$2K business class fares to Portugal. They also have a stopover program that lets you enjoy a few island days (which I can never have too many of).

The other interesting one is Icelandair to Reykjavik. Iceland is great. I spent 6 days driving through nature, camping and staying in B&Bs.

Just know, Icelandair and Azores business class are not the full lie-flat luxury situation people usually imagine, it's more like premium economy, so take that one with a grain of salt.

Business-Class Flight Deals:

• Boston to Reykjavik | Nov 9 to Nov 19, 2026 | $1,786 RT | Icelandair | nonstop | Google Flights​
• Boston to Porto | Nov 9 to Nov 19, 2026 | $1,823 RT | Azores Airlines | 1 stop | Google Flights​
• Washington to Reykjavik | Sep 8 to Sep 18, 2026 | $1,909 RT | Icelandair | nonstop | Google Flights​
• New York to Porto | Dec 9 to Dec 19, 2026 | $1,916 RT | Azores Airlines | 1 stop | Google Flights​
• Boston to Lisbon | Jun 9 to Jun 19, 2026 | $1,932 RT | Azores Airlines | 1 stop | Google Flights​

If you end up booking one of these, please let me know! Also, if you'd be open to flights at a higher price tag (e.g. $2.5k, $3k - which then makes finding lie-flat way more possible), just reply to this email with that number and I'll adjust my search.