EVORA, Portugal — Around 3 p.m. this past Tuesday, I stood just outside the wall of this ancient city in Portugal’s southern, and mostly rural, Alentejo province, play-acting a scene of storming the city. 

With me were my four teammates, each a travel advisor. Two of them, Kathy Campbell of Frosch and Eve Primeau of Quebec-based Voyage Gendron, stood behind and in front of me, pretending to spring through a small city gate.

A third, Fallon Dragland (love that last name) of Canada’s EF Education First, lay sprawled on the cobblestone, pretending to be dead. Standing over her was Emma Sutton of Exito Travel, who wielded a tube of sunscreen as if it were a knife. 

Our immediate goal was to come up with a photo that paid homage to Reconquista hero Geraldo sem Pavor, the warrior who seized Evora from the Moors during the 12th century. But the team’s bigger goal was to win this year’s Air Canada/United Airlines Race, and with it a free return trip for two to the region for each of the team’s travel advisors. An evocative photo of Gerald the Fearless just maybe could provide the crucial extra points needed for victory. 

This educational and enrichment exercise, which is modeled after longtime TV show “The Amazing Race,” has been an Air Canada staple since 2006. This year, in conjunction with the deepening of the transborder partnership between United and Air Canada, United joined in on the fun.

Fifteen advisors from Canada and 15 from the U.S. won an invitation to Portugal this week to participate in the competition and to take a deep dive into the Alentejo region, which is a prolific producer of olive oil and a burgeoning wine producer. Alentejo also tempts outdoor enthusiasts with lots of open space and a mixture of plains and seascape. 

It’s an event that Air Canada says is designed to increase brand awareness and drive revenue. And United’s sales manager for meetings and incentives Stacey Nishikawa told me that United views the weeklong fam as an opportunity for agents to experience United’s flights to Lisbon from Washington National and Newark.

It’s also helping to educate travel advisors about Portugal, which lately has become an “it” destination for North Americans. United will fly four routes there this summer, having added summer service from Newark to the Azores last year. 

Over the course of more than seven hours on Tuesday, the race transformed my team of office professionals into something akin to excitable children. More or less without rest, we scurried up and down the hilly streets of Evora, keeping appointments with local shopkeepers while trying to complete assigned tasks, such as our photo at the city wall or a handwritten article we were assigned to write promoting Alentejo. 

At one point, we imposed upon a large group of adolescents, convincing them to look at the camera from behind us as we took a group selfie. Later, we recruited a local police officer to pose with us. Both photos completed race assignments. 

At various shops, local merchants had games waiting for us. A wine seller had us take a blind taste test of three glasses of red, and we had to decide if those wines were each different, if two were the same, or if they were all the same. For 15 minutes we tasted and swished and smelled. Then we guessed wrong. 

At a small café, we played a Pictionary-type game, but with only local themes. That one we aced. So, too, with the ice cream taste test. You might not be able to identify pastel de nata ice cream in a taste test. But we did. If you want to gain said skill, I suggest a visit to Portugal. 

Despite all this hurrying, 40 minutes before the 4:30 deadline to complete the race we realized we had several assignments left to complete. Furiously we set off on those last tasks.

Soon thereafter I found myself sprinting through Evora, determined to get the article, which I had taken responsibility for writing, in on time. Sweaty and winded, I made it back to our hotel, the Vila Gale Evora, in the nick of time and joined my teammates in submitting our folder at precisely 4:30. 

Alas, our efforts were not enough to win the six-team competition. Apparently, not even that inspired reenactment at the city gate was enough to do the trick. 

But the race on a whole felt like an unmitigated success. At the post-race dinner that night, travel advisors who were strangers 12 hours earlier joked with familiarity, having forged meaningful connections. I heard a few saying it was a day they’d never forget. 

Sutton, my teammate, summed things up when she told me that the race was a great and memorable way to dig into Evora and Alentejo. 

“It was a lot of fun. The challenges were interesting. And the team I was matched up with was unparalleled,” she said. 

Indeed it was, I agreed.

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