The email that's gotten us a hotel suite almost every time

Everybody wants the points hack with the big number on it. This isn’t that. This one is free, it takes about four minutes, and it has worked for us more reliably than anything else in our whole playbook.

Before we check into a hotel — doesn’t matter if we paid cash or booked it on free nights — I track down the person who actually runs the place. Not the 1-800 number. The hotel manager, or whoever heads up guest relations at that specific property. Then I send them a short, warm, completely genuine note.

That’s the whole hack. And we’ve sat in a suite in New York that would have run thousands a night, a big one in New Orleans, one in Paris, one in Jackson Hole, one in Maui. Not every time. But close to it.

Why it works

A hotel has empty better rooms more often than you’d think. Upgrading a guest who’s clearly going to be lovely about it costs them almost nothing and buys a good review, a repeat stay, a story. You’re not asking for a discount. You’re giving them an easy reason to make someone’s trip — and telling them, in advance, that you’ll be the kind of guest worth doing it for.

The whole thing lives or dies on tone. The second it reads entitled, it’s dead. Done right, it reads like a real person who’s genuinely excited to stay there.

When to send it

About a week before you arrive, in the hotel’s local morning — that’s when the front-desk and reservations team are fresh and not buried. Find the email by calling the property and asking for the manager’s address, or a few minutes of Googling the property name plus “general manager.”

What to actually say

Here’s the shape we use. Make it yours — the specifics are the point.

Subject: So looking forward to our stay (the Ice family, arriving [date])

Hi [name] — I’m Jamey, and our family of four is staying with you [dates]. We’ve been looking forward to this one for months; it’s [the girls’ first time in Paris / our anniversary trip / a long-overdue week off], and I’ve heard such good things about [the property].

I know upgrades are always first-come and never a guarantee — but if anything happens to be open when we arrive, even a room with a bit more space for the kids, it would honestly make the trip for them. Either way, we’re thrilled to be staying with you. I’ve attached a photo of the crew so you know who to look for.

Thank you — see you soon. Jamey

Attach a nice family photo. Mention your loyalty status if you have it. Name the occasion — an anniversary, a birthday, a first trip — because that’s the thing that makes a stranger want to help.

Then let it go

A friendly face at check-in roughly doubles it — the email plus a real, warm conversation at the desk is the combination that lands. And if nothing comes of it, never push. Gratitude is the entire currency here; we don’t follow up twice. The worst case is the perfectly good room you already booked, and you’re out four minutes.

This is one chapter of the bigger system — the cards, the transfer-partner sweet spots, the kid logistics. If you want the whole thing, it’s in our travel-hacking playbook.