New points sweet spot to Italy

Goooooooooood morning from Dakar, Senegal. 🇸🇳

It sounds glamorous, but my days here are the same as anywhere else – hunched over a laptop, writing about points, and trying to set the record for most coffees consumed in a single day.

Let’s finish off the week with a bang:

• ✈️ An exciting new airline partnership

• 🏨 Book three nights in Cabo for $349 (with a catch)

• 💪 Daily Drop Lounge win

• 💳 Current Transfer Bonuses

✈️ An exciting new airline partnership

Well, well, well… Aeroplan just gave us a new toy. You can now book ITA Airways flights using Aeroplan points… yay!

If you’re not familiar, ITA is Italy’s flag carrier, and they fly nonstop from Rome to a ton of North American cities, including:

• New York

• Boston

• Washington, D.C.

• Chicago

• San Francisco

• Los Angeles

• Miami

• Houston

• Toronto

Translation: this just unlocked a bunch of new nonstop options to Italy (and beyond).

What does it cost?

Because ITA prices under Aeroplan’s distance-based partner chart, the rates are actually… solid.

For example:

A nonstop from New York City to Rome on ITA will run you 40,000 points in economy. It’s far from the best deal out there, but it’s nice to have the option.

And here’s the fun part…

You could continue onward to cities in Germany, France, Spain, or even Greece for the same 40,000 points, as long as you stay within the same distance band.

So instead of just Rome, you could do:

• New York → Rome → Athens

• New York → Rome → Munich

• New York → Rome → Nice

Same pricing. More pasta, beer, gyros, and… whatever they eat in France. 🐌

It’s not just Europe…

ITA isn't good for just European flights. They fly to some cool countries, including Thailand, Brazil, Japan, and even where I'm currently writing from in Dakar, Senegal.

For example, a nonstop from Rome to Dakar will run you 25,000 Aeroplan points in economy, which is excellent for a 6-hour flight to Africa.

Want to get fancy with it?

That same route prices at just 45,000 points in business class – which means you could try ITA’s sleek narrowbody lie-flat seats on their A321neo.

Build a multi-continent trip

Aeroplan allows you to add a stopover on a booking for just 5,000 extra points each direction, which means…

You could book a flight from the U.S. to Rome, spend a week there, then continue onward to Asia, Africa, the Middle East, or another European country.

And it will only cost you 5,000 more points than what you’d pay to have a layover in Italy.

I know that sounds a little confusing, so check out this newsletter for more details on how that all works.

Why this is so useful

Unlike some sweet spots out there, this one is super accessible because Aeroplan points are ridiculously easy to earn.

You can transfer points to Aeroplan from:

• UR points

• MR points

• Capital One miles

• Bilt Rewards

Aeroplan also has a co-branded credit card, which could be a good option for people who use Aeroplan points regularly.

What’s next?

ITA is in the process of joining Star Alliance, which means this partnership will likely deepen over time.

For now, though, this is just another strong global airline you can tap with one of the easiest-to-earn points currencies out there.

And we will absolutely be tapping it.

🏨 Book three nights in Cabo for $349 (with a catch)

Every seasoned traveler eventually gets one of these emails.

It’s always something like:

“Exclusive invitation. Luxury villa. Limited-time offer.”

And the price is suspiciously low. 🤨

This week, World of Hyatt offered me a 3-night stay in Cabo for $349 at Hyatt Vacation Club Sirena del Mar. One-bedroom villa, ocean view, the works.

At first glance? That’s kind of absurd value.

But then you scroll a bit, and there it is. The timeshare presentation. *cue dramatic music*

What this means

If you’ve never encountered one of these before, here’s the genre:

Hotel chains offer heavily discounted stay packages at their vacation club (a.k.a. timeshare) properties.

In exchange, you agree to attend a sales presentation where they try very hard to convince you to buy a timeshare.

For my offer, the presentation clocks in at approximately 120 minutes. 😬 And if you skip it? They charge you the full retail value of the stay.

Now here’s where it gets interesting.

On top of the $349 villa stay, they’re offering either:

• 7,500 bonus Hyatt points, or

• A $100 resort certificate

And 7,500 points is not nothing…

For example, that’s enough to book a free night at a nice property like this Hyatt Regency in the U.K. and still have some left over:

So in theory, you could:

• Fly to Cabo

• Sit through two hours of “imagine your legacy”

• Say no a bunch of times

• Enjoy a 3-night stay on the beach

• Collect 7,500 points

• And then use those points for a free night somewhere else

That sounds pretty darn good if you ask me.

Let’s talk about the real question, though:

Is this worth it?

If you are:

• Extremely comfortable saying no

• Immune to high-pressure sales tactics

• Not emotionally vulnerable to “today-only pricing”

• And financially disciplined

Then yes, this can absolutely be a strong value play.

If you are even slightly tempted by phrases like “investment in memories,” this might not be your battlefield.

Because these presentations are designed to wear you down, there’s usually a handoff to a manager. Then another “final” offer. Then a slightly smaller “just to make it easier” version.

What it comes down to is paying $349 and two hours of your life for a heavily discounted vacation and some bonus points.

Check out Hyatt Vacation Club and/or your email inbox for similar offers, and good luck out there. 🫡

💪 Daily Drop Lounge win

There’s a very specific fear that almost everyone has when booking their first award flight. It goes a little something like this:

You finally find business-class award space…
You transfer your points…
And by the time they hit your account?

Gone. Poof. The flight disappears, and someone else is sipping champagne in YOUR seat. It’s just rude.

The other day, someone posted in the Daily Drop Lounge with a trick that eliminates this fear entirely:

They called Flying Blue to hold two LAX–Athens business-class tickets.

It cost $30 to secure the seats for 24 hours. Then, they transferred Capital One miles to Flying Blue.

The points were posted about ten minutes later. They called back and ticketed the reservation.

No stress. No racing the clock. No gambling on transfer timing.

Not every program allows this, and sometimes there’s a small fee involved – but when it’s possible, it completely removes the biggest psychological barrier in this hobby.

That’s the kind of tactical edge you only learn from people actively booking real trips.

If you want access to more wins like this (or want to share a win of your own), that’s exactly what the Daily Drop Lounge is for. 👇

That’s all for today, my friends. I’m getting dangerously close to this newsletter taking more than 5 minutes to read, so I’m going to leave it there.

Have a great weekend ❤️

14.7167° N, 17.4677° W

With contributions by McKay Moffitt