Weekend Edition / Dear Ohad...

ANA First for 55K? Hyatt villas with cliffside pools? Flying Blue glow-up? We're not here for basic bookings—we're here for "Dom" @ 38K feet & 6K-point Venice suites. Stop hoarding, start flexing. Your points deserve a better life—and so do you.

Weekend Edition / Dear Ohad...
📸: Taking your questions from a remote & secluded beach on Maui, Hawaii 🌅💕🌴🌊🍧
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Dear Ohad,
I want to take my family of 4 to Italy this summer. We’ve got 400K Chase points and maybe three days of date flexibility. Be honest—do we stand a chance, or should I just cry now?
— Planning and Panicking

Dear Panicking,
You’re not doomed, but you’re definitely in the “may require miracles” zone. Summer to Europe is peak insanity. That said, here’s your battle plan:

  • Air France/KLM Flying Blue: Your best friend. Search JFK/BOS/ORD to Rome/Venice/Naples. Even 4x economy seats at 25K–35K each is a win.
  • Iberia: If you can split up slightly or fly from JFK to Madrid, it’s ~34K each way in business during off-peak. Then connect.
  • Consider a hybrid: Biz for the adults, economy for the kids. They’ll bounce back. You won’t.
  • Last resort: Book one-way with points, one-way with cash.

TL;DR: You’ll sweat, but you won’t cry. Yet.


📸: That feeling when the cash price drops after you used points...
😬
Dear Ohad,
Booked Hyatt Ziva Cabo with 25K points/night… then saw cash rates drop to $289. Did I mess up?
— Post-Booking Blues

Dear Blues,
Only slightly. You probably still got 1.1–1.2 cents per point, which is fine—not amazing. But next time, run the math before booking:

  • If you're getting under 1.5 CPP for Hyatt, consider paying cash.
  • Pro move: Book with points, monitor cash rates, then rebook and cancel if needed.

Don't beat yourself up. It’s still better than spending those points at a Hyatt Place in Toledo.


📸: TWA hotel at JFK terminal 5... but make it ✨date night✨
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Dear Ohad,
I’ve got 80,000 Amex points and a girlfriend I’m trying to impress. Can I do a baller weekend in NYC or am I doomed to airport hotel vibes?
— Romantically Optimistic

Dear Romantic,
You're in luck. 80K Amex can be turned into “damn, he’s got taste” if you do it right:

  • Virgin Atlantic used for for Delta One (lol, good luck).
  • Or go for hotels: Transfer to Choice and book The Draper NYC (Ascend Collection) at 16K–20K/night = 5-star vibes on a 3-star budget.
  • Or hit the Thompson Central Park via Hyatt transfer.

Dinner is on you, though. I don’t do OpenTable hacks.


📸: Turkish Airlines’ customer service line / Not sure she's really smiling though
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Dear Ohad,
I transferred 100K Citi points to Turkish to book a United flight. It’s been a week. Still no ticket. No one’s answering. Did I just get scammed?
— Turkish Hold Music

Dear Hold,
You got points-play punk’d—but not irreparably. Here’s the breakdown:

  • Turkish has phenomenal sweet spots (e.g., 15K one-way US domestic biz), but their back-end is run by carrier pigeons.
  • Call early in the morning (like 5–7am ET), or email their US ticketing office directly.
📲
ProTip: Use the mobile app for redemptions—it sometimes works better than the desktop.

No scam, just pain. Next time, bring a travel hacker emotional support buddy.


📸: Screenshot this before the internet deletes it / Japan Airlines inventory via JetBlue
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Dear Ohad,
I have 300K Capital One miles. Can I fly business to Tokyo, or did I back the wrong horse?
— Miles and Regret

Dear Regret,
You didn’t back the wrong horse—you just need to feed it the right transfer partner:

  • Transfer to Avianca LifeMiles → Book ANA biz class for 75K one-way.
  • Or to Turkish → Same redemption for 90K roundtrip… if you like suffering (see above).
  • Also works via Emirates, Cathay, or Etihad depending on routes and quirks.

Capital One isn’t the problem. Lack of patience (or redemption literacy)? That’s another convo.


📸: Definitely real, definitely overwhelming / Note they plan to stop issuing round-the-world tickets as of June-23-2025 (US Time Zones)

🤳
Dear Ohad,
Saw someone post a round-the-world trip on Reddit using points. Is that real life or just influencer fiction?
— Skeptical but Hopeful

Dear Hopeful,
It’s real—and usually borderline deranged. But magical.

Actual examples that work:

  • ANA RTW ticket: 125K–145K miles in biz. Up to 8 stopovers. Only roundtrip. Requires calling Japan. Worth it.
  • Custom DIY with stopovers: Use Aeroplan or Asia Miles. Piece together Oneworld/Star Alliance.

You’ll need:

  • Patience
  • A spreadsheet
  • Low blood pressure
  • A one-way ticket to chaos

Would I do it? Yes. Would I recommend it to my sister? Absolutely not.


📸: Delta One, now starring emotional damage
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Dear Ohad,
I booked Delta One to Paris for 370K SkyMiles roundtrip. Please roast me gently.
— Regretfully Loyal

Dear Loyal,
Oh honey. 370K? Did the SkyMiles team steal your lunch money too?

  • Real talk: You paid the equivalent of $3,700 in value for a seat that retails around the same. So… meh.
  • For comparison: Air France biz = 50–70K. Virgin Atlantic = 47.5K off-peak.
  • It’s not a total disaster if your dates were peak, last-minute, or if you just really like those Delta salt shakers.

Roast level: medium rare. Next time, transfer those Amex points somewhere where they’ll stretch—not scream.


Until next time…
Don’t book like a basic traveler. Think like a spreadsheet nerd with a passport. You deserve better than inflated Marriott redemptions and 370K SkyMiles regrets.

Got questions? Redemption regrets? Booking wins you want to brag about? Send them to newsletter@upnonstop.com and we’ll turn your points panic into premium cabin therapy.