From Deal to Departure: How Flight Alerts Shape Our Travel Life ✈️

My husband loves a good deal. And I mean really loves them. Whether we’re on the beach or backpacking across Southeast Asia, he’s the type to pull out his phone mid-sunset to send our friends a $500 round-trip to Europe he just spotted. He’s subscribed to Vol d’Alexis, Jack’s Flight Club, RedFlagDeals—you name it. Sometimes he even buys things on the go, with a quiet thank you to our families back home who graciously receive our packages while we’re abroad. 🙈

Let’s be honest—how many of us are affected by “buy now, think later”? (Guilty.)

The Sabbatical Shift

Our travel style really changed when we took a sabbatical. Suddenly, we weren’t bound to school vacation calendars anymore (I was a teacher), which meant we could finally jump on deals outside of Christmas, March break, or summer—typically the most expensive times to travel.

With flexible time, flight deal alerts went from “tempting” to “let’s book it.”

June 22, 2024: The Deal That Got Us

We were playing tourist in Montreal with a visiting friend when it happened. A 2-for-1 deal popped up—Azores and Cape Verde in the same trip. My husband pounced. These deals don’t last long, and the earlier you book, the more flexibility you get. But let me tell you—booking on a whim isn’t always as romantic as it sounds.

The questions start flying:

• Where are we going exactly?

• Which dates work best?

• How many days in each place?

• Do we need a rental car?

• Is it safe?

• How expensive are the hotels?

• Any vaccines or visas needed?

• Can we find gluten- and dairy-free food?

  
  

It’s a fun kind of stress... most of the time.

Minimal Research, Maximum Leap

We booked the trip for May 2025 via FlightHub with SATA Airlines. All we knew was: they’re both island destinations, and the deal was too good to pass up. That’s it. No deep dives into history, safety, or logistics—just vibes.

Later, SATA changed our flight from the Azores to Cape Verde, pushing it earlier by a day or two. That meant we had to adjust our Montreal–Ponta Delgada flight too. Cue hours on hold with FlightHub and SATA.

And then there was the visa situation.

A Visa Oversight (Almost)

I assumed we’d be fine—Portugal (Azores) is easy for Canadians, and Cape Verde used to be a Portuguese colony. But I totally forgot to double-check. We caught the error six days before our flight. 😅

Turns out, we needed to fill out an EASE form and pay a 3,400 CVE fee at least five days prior to arrival. The link on the Government of Canada website? Broken. We found help through Reddit and TripAdvisor, then successfully submitted our application. At the airport in Praia, the electronic system worked smoothly.

Lesson learned: spontaneity is great—but so is checking visa requirements early!

Island Life in Cape Verde

Once in Cape Verde, we chose to visit Sal Island, home to the only Hilton hotel in the country (a little splurge). But getting there meant another flight—from Praia (on Santiago Island) to Sal.

To play it safe, we stayed two nights in Praia before flying to Sal, and one more night there on the way back to the Azores. Island-hopping can be tricky, especially when you have international flights to catch!

Final Thoughts

We’ve definitely leaned into the “deal chaser” lifestyle. Sometimes it’s impulsive, sometimes it’s chaotic, but almost always—it's rewarding. From last-minute visa scrambles to learning about places we hadn’t even Googled before booking, this style of travel keeps us on our toes.

And anyone who knows my husband will confirm this. He is the deal chaser. If there’s a deal or a flight alert, he’s already seen it. If there’s a price drop, he’s halfway through booking it.

Honestly? We wouldn’t have it any other way.