Diana Winters can't remember a time when her life didn't involve travel.
“My entire career has been in travel,” says Winters, who has worked in “this wonderful, crazy business” for 24 years. “I started as a travel agent, fresh out of travel school. In fact, I had an interview the day after I graduated from Mohawk College and got the job. The rest, as they say, is history.”
Winters was born, raised and currently lives in Hamilton, ON (“I’m the proudest Hamiltonian around. I'm a Hammer girl through and through,” she says).
Her day-to-day duties revolve around building relationships with travel agents and teaching them about her company’s brand through FAM trips and training.
“I truly believe it is my responsibility to ensure that [agents] have maximum exposure to my brand so they know it better than I do,” she says.
Here, PAX checks in with Winters to chat about her inspiring trips to Macedonia, a souvenir that she refuses to lose sleep over and that time she ended up at a rave with Bjork.
PAX: What are three essential items you always travel with?
Diana Winters (DW): Protein bars (’cuz you never know), baby wipes (’cuz, well, you never know) and my toothbrush.
PAX: What are some of your favourite vacation spots (and explain why you like them)?
DW: Macedonia, hands down, is my number one. My roots are Macedonian. I'm a first generation Canadian to Macedonian immigrant parents. This is, by far, one destination that is a hidden European gem. The warmest people, incredible history, phenomenal cuisine and home to UNESCO World Heritage Sites. The most inexpensive European holiday you could ever have, without question.
Italy is the next runner up. I love, love Italy. It's the most romantic country in the world. People watching, getting lost among the locals in cities. The food – so rustic and earth to table. The simplicity of it all and just coming back to the basics is what makes me go back. So much history and beauty to see, my eyes frantically trying to take in as much as possible. It's a complete sensory overload.
PAX: What’s your favourite airport and why?
DW: John C. Munro International Airport. Oh, that's Hamilton airport in case you were wondering. I love it because you park right out in front of the departure entrance, check in as soon as you walk in, walk another 20 feet to the Tim Horton's for a coffee, walk another 20 feet for the security check point, and you're in. Another 50 feet and you're at your gate.
Fancy airports and massive shopping mall terminals don't turn my crank at all. The simpler, the better.
PAX: What do you love about your job?
DW: This is easy. The relationships I've made along the way. This industry is quite big but really, it's very small and tight knit. I've come to know people that have become lifelong friends, some that I've been friends with for as long as I've been in it. I can say without any hesitation that I have a travel family that loves me just as much as blood relatives do. As well, I have had the privilege of mentoring and coaching quite a few agents along the way. Watching them succeed is truly the feather in my cap.
PAX: What was the first vacation you ever took?
DW: I was eight-years-old when I took my first plane ride. It was to Macedonia with my mother, grandfather and older brother. It was memorable because I went to the villages where my grandparents were born, learned about the war they fought in and stood in the very same spots where family members lost their lives fighting for freedom. It had such an impact on me; travelling through the same mountains that my grandparents fought in; walking on the same trails my great-grandmother travelled along with many of the village children, trying to spare them the terrible fate that others weren't so lucky to escape.
It was a trip I never forgot and because of the deep loss and history, it is a place that will always be so important to me. It was for this very reason I took my son in 2017. It's a rite of passage. We all should know where we came from.
PAX: What’s the biggest splurge you’ve ever made on a trip?
DW: Here's a fun fact about me – I'm really a simple woman. I'm not impressed by things. I want experiences. Buying a purse or a watch or shoes for obscene amounts of money I'm sure would bring me joy for about 15 minutes [but] that $500 Italian rail pass brought me so much happiness.
Although I will confess, last summer I did find a ring in Macedonia that I have wanted for most of my life and just could never find it. Well, I found it. It's a rare 500 Turkish Kurush coin that is almost completely pure at 23 karats. I saw it and had to have it and didn't care what it cost. Let's just say that I sleep very well despite the nauseating price tag.
PAX: What’s the most memorable meal you’ve ever eaten while travelling?
DW: I've had so many that it's hard to really choose. However, one that stands out for me was just this past August. I was sitting in a restaurant in the heart of the Piazza del Duomo in Florence looking directly at the Santa Maria del Fiore Cathedral. I enjoyed a bottle of Chianti and a simple spaghetti cacio e pepe. The bells of the cathedral chiming, the grand site of the cathedral before me and the simplest meal made it a truly incredible experience. Somehow in that moment, I believed that was the best meal I had ever had. Travelling alone brings a heightened awareness to so many of our senses.
PAX: What’s your biggest travel pet peeve?
DW: Well, the lack of travel etiquette makes me crazy. How about if you're sitting at the back of the plane, you should wait for the rows [ahead of you] to exit before you do. It's hard not getting Hamilton on people.
PAX: What are your hidden talents?
DW: I'm a wizard in the kitchen. I can cook just about anything but take great pride in my abilities to make Macedonian cuisine taste just like my grandmother's did. The bigger the crowd to cook for, the better.
PAX: Checked bag or carry-on?
DW: Checked, although it really depends on where I'm going and for how long. I'm getting better though. I spent a month in Europe and did it with a small suitcase and a backpack.
What's your funniest travel anecdote?
DW: Remembering that time when I was turning 18-years-old and was in Macedonia. As a birthday gift, my grandmother paid for me to go with my friends by bus from Macedonia to Hungary to see the Rolling Stones during their Voodoo Lounge tour. Crazy that she even let me go considering the Balkan War was alive and well. Fast forward to Budapest. Stayed in a youth hostel and had a blast with my friends, the concert was insane. We then roamed the streets of Budapest looking for the party.
We ended up in an underground rave that looked like something out of a movie. Seedy, dark, smoky and loud. It was an awesome night of dancing and newfound adult freedom. But what made the night even better was dancing without a care in the world only to discover that Bjork was dancing right behind us. It was awesome.
PAX: What are some key things that travel agents should be aware of right now in regards to Palace Resorts and LeBlanc Spa Resort?
DW: We are a brand that is focused on service and quality. Our repeat client base is extraordinary and speaks to the quality of our brand. Our offerings are second to none and what is standard to us is considered an upgrade to our competitors. We are committed to the highest quality and are equally as committed to our travel agent partners. The resort credits, for one, is a promotion that was created by Palace Resorts and is actual cash to use towards excursions, spa, golf...etc. Our incredible 'Kids and Teens 17 and under" stay and eat free promo pairs with beautiful locations, luxurious accommodations and service fit for a queen. Join me for a week on one of #DianasAwesomeFams and, I promise you, I will change your life.