Weekend Edition / Dear Ohad...

Dear Confused,

First of all, unless the boat comes with free champagne and a captain who knows how to sweet-talk Marriott into an upgrade, I’d keep the points on dry land.

Here’s the deal: Amex points are like that friend who somehow gets invited to every party—extremely flexible. Transfer to airline partners if you’re aiming for high-value redemptions (think business or first-class international flights where you’re sipping "Krug" at 35,000 feet like you invented the airplane). But if you're looking for simplicity, Amex’s hotel partners or their travel portal can work, especially during transfer bonuses.

But do not—I repeat—do not cash them out at 0.6 cents per point unless you hate joy. These points can easily be worth 2 cents or more with the right flight. Use wisely, my friend, and you’ll never see coach again… unless you’re just heading back there to grab your forgotten neck pillow.

Dear Skeptical,

Two words: Domestic. Economy.

Listen, using 25,000 miles for a $200 flight between Chicago and Kansas City feels like paying $100 for a salad at an airport Chili’s. Sure, it might technically "work," but you’ve squandered potential.

Save your miles for international flights where cash prices are absurd. Or at least shoot for premium cabins. Think: 60,000 points for a lie-flat seat to Europe vs. spending the same on a two-hour hop with no legroom and a Biscoff cookie.

"But Ohad, I need to get to my cousin’s wedding in Des Moines!" Fine, but that’s why we pay cash. Redeem big where it counts, and leave the short-hauls to your wallet.

Dear Ice Machine Survivor,

Ah, welcome to the sacred world of elite status and sweet-talking front desk agents. If you want to trade the ice machine for an ocean view suite, here’s the playbook:

1. Get status — Either organically (stay loyal) or through credit card perks (we love a shortcut).
2. Be human — A smile, a chat, and a simple “Any chance there are upgrades available today?” can work wonders.
3. Travel smart — Check in at off-peak times when the hotel isn’t slammed. Arriving at 11 PM on a Tuesday? Jackpot.
4. Milestone properties — Certain hotel brands (cough, Hyatt Globalist) treat elites like royalty. Marriott? Well, it depends on whether Mercury is in retrograde.

And if all else fails? Write a charming note requesting a quiet room away from the ice machine—maybe even with a small bribe of locally famous cookies.

Dear Economical,

Ah, the eternal question: Lie-flat bed with champagne or knees jammed into the seatback of a toddler playing the bongos on your headrest?

Business class is where your points get their wings. It’s less about luxury (although, yes, sipping rosé at 35,000 feet is divine) and more about ARRIVING like a functioning human. If you’ve ever landed after 12 hours in economy feeling like a fossil, you know the difference.

However, if you’re young, nimble, or simply stoic, go economy and stretch those points for more trips. If you’re like me and consider neck pillows a conspiracy, go business.

Life’s short. Your points shouldn’t be.

Dear Adventurer,

Let’s be honest, the Maldives is stunning but also overrun with honeymooners and people who say things like “we only do luxury eco-resorts.” Want something fresh? Try these:

• Oman — Use points for the Al Bustan Palace or Six Senses Zighy Bay. Think desert meets ocean meets Bond villain lair.
• Slovenia — Fly into Ljubljana, use points at boutique hotels, and enjoy lakes, castles, and zero influencer crowds.
• Kyoto — Skip Tokyo for once and dive into Kyoto’s hidden ryokans (many bookable with points via portals). Plus, matcha everything.
• Seychelles — Maldives vibes without the Maldives hype, and plenty of properties where you can redeem Hyatt or Hilton points.

Points are your magic carpet—go where others don’t.

Dear Dreamer,

Oh, it’s real. Emirates First. Singapore Suites. Lufthansa First Class Terminal with its own private whiskey bar (yes, it exists). And all bookable with points… IF you know where to look.

Pro tip:

• Emirates — Transfer Amex or Capital One points to Emirates Skywards.
• Singapore Suites — KrisFlyer miles, baby.
• Lufthansa First — Book via partners like Aeroplan or LifeMiles, but only 15 days out. It’s like playing travel roulette.

It takes patience, alerts, and a touch of obsession, but I’ve personally booked $10K+ flights for under 100,000 miles and a few bucks in taxes. So yes, that champagne and caviar selfie? Fully legit. Just don’t spill it on your PJs—they hand them out onboard.

Dear Edge-Seeker,

Stop sleeping on stopovers and open-jaws! They’re the hidden gems of award travel.

With programs like Air Canada Aeroplan or Alaska Mileage Plan, you can add a stopover for as little as 5,000 extra points. Example:
Fly New York ➡️ Tokyo (stop for a week) ➡️ Bali, all on one award ticket. Double the destinations, same lie-flat glory.

Or book an open-jaw: fly into Rome, out of Paris, and skip backtracking for free.

It’s like ordering a side of fries that also comes with truffle oil, parmesan, and the chef’s private stash of black garlic aioli. Delicious and efficient.

Dear Guilty,

I wouldn’t say I judge... but yes, absolutely. Points are like avocados: they’re great now, questionable in a year, and mushy by the time you finally try to use them.

Between devaluations, inflation, and airlines playing games with award charts, there’s no prize for having a million points in your account and no trips booked.

Use them! Travel! Burn them on that ridiculous first-class trip to Tokyo or that overwater bungalow in Bora Bora. Points are meant to be memories, not spreadsheets.

Dear Maniac,

When you start calculating the points value of every cup of coffee or judging people for booking hotels directly instead of via a portal, it’s safe to say you’ve entered... The Points Matrix.

But hey, worse addictions exist. Just remember: points are a tool, not a lifestyle. Use them to enhance your life, not run it. Also, it’s okay to pay cash sometimes—I promise the award travel police won’t confiscate your Priority Pass.

Until next time, keep earning, keep burning, and for the love of upgrades, don’t pay cash for domestic economy—unless, of course, you enjoy regretting life choices. And remember, if you’ve got more questions (or just need someone to commiserate over award booking disasters), send them my way at ohad@upnonstop.com.