Hello from Apple Park!

I'm at the tech giant's campus to get a first look at all the new software features coming to our Apple devices.

I doubt any new hardware will be released today (we'll have to save that for the fall), but I'm particularly excited to see which improvements will make the travel journey easier. (Hello, upgraded AI?)

Either way, I'll recap the announcements on Wednesday.

In the meantime, here's everything else going on.

Advertiser and Editorial Disclosure

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I’ve already outlined how you can turn those points into a variety of free trips.

I also shared why my mom, who only has the American Express Platinum Card®, and my wife, who only has the Chase Sapphire Preferred® Card, got in on this offer.

(Yes, you read that right. If you have the Preferred, you can double dip and still snag this offer.)

Here’s my referral link for the offer.

(Quick note: if you end up applying through my link, I'll earn a small commission that keeps this newsletter free. Thanks in advance.)

Each month, I share an update on the latest styles and gear I've been eyeing.

Here are my recent picks from April and May. Below you'll find updated choices for June as summer kicks off.

Men

Gear

My wife's picks will drop later this week, once she finishes putting her list together.

Some fun news: Cathay Pacific tapped me as an expert panelist for the carrier’s Members' Choice Awards 2026. I helped shortlist the finalists, and now it's your turn to crown the winners.

The awards span 15 categories across hotels, dining, travel, Hong Kong, and global destinations.

I'll be honest — the finalist list is stacked. Think Park Hyatt Tokyo, Rosewood Hong Kong, and even one of the best coffee shops in NYC, Devoción.

Voting runs through June 21, and the winning brands will put together offers and experiences for voters, so it's worth two minutes.

To get to San Francisco, I purposely didn't fly United — even though the airline runs plenty of flights between its Newark and Bay Area hubs.

Why?

Because United's widebody jets that fly between the coasts are outfitted with Panasonic Wi-Fi that's been virtually inoperative on most flights lately.

I work on basically every daytime flight, and reliable Wi-Fi is a key factor in how I book. Until Starlink is installed, I'm avoiding any jets with Panasonic when possible.

If you want to dodge a similar fate, here's a list of the planes to avoid booking:

Of all U.S. airlines, United is by far the strictest about duplicate reservations.

Book two flights that seemingly conflict, and you'll get an email within an hour warning that your duplicate tickets will be canceled. (Word to the wise: United follows through.)

But here's where the duplication engine gets annoying.

I was booking United flights for my wife from Europe to the U.S. She isn't sure whether she'll come home on a Monday or Tuesday, so I booked both to lock in the award availability I found.

Within an hour, I got the duplication warning, even though the flights don't conflict. She could theoretically make both (if she flew back and forth to Europe — something I’ve done before).

The only workaround I've found is to book the second ticket without the frequent-flyer number attached.

United seemingly doesn’t want people holding seats from other travelers, but in this case, the algorithm is flagging flights that don’t actually conflict.

Something to be aware of if you’re booking United.

Earlier this year, I was disappointed by the state of American's poshest jet, the Airbus A321T. (Think: wear and tear, peeling seat covers, missing menus.)

To get to San Francisco, I decided to give the A321T another try — largely because the free Viasat Wi-Fi is as good as it currently gets between the coasts.

Well, I guess no one at Skyview acted on my last experience.

This time, my seat had a broken in-flight entertainment system and power outlet. I couldn't care less about the TV, but power is as essential as Wi-Fi when I'm trying to work.

Stay tuned for what I get as compensation — if anything.

Last week, my former employer crowned the best airline in America.

I won't spoil their pick — but I want to hear from you first.

I recently got an email from a reader asking my thoughts on skiplagging.

For the uninitiated, that's the practice of booking a flight to a destination you have no plans to visit, then getting off at one of the connecting cities along the way.

Skiplagging (or hidden-city ticketing, in expert parlance) can sometimes yield cheaper fares. It's not illegal, per se, but it is against the rules of every major airline.

Personally, I never advise friends or family to do it.

Can you get away with it once or twice? Probably.

But all it takes is one delay, cancellation, or gate-checked bag for your plans to go sideways.

Plus, you could get your loyalty account suspended, get banned from the airline, or be asked to repay it for the flight you took.

I'd just invest more in boosting your points balance rather than relying on skiplagging.

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