“We’ve known each other since we were kids!” shares Allie Herbert of her relationship with Leo Mastoras, which began when she was just nine years old. Allie’s best friend is Leo’s younger sister, so while they knew one another, it wasn’t until his sister’s 21st birthday party that they exchanged phone numbers and got to know one another as adults. “There may have been crushes from a younger age, but we have a four-year age gap, so we never overlapped in school or life chapters until we were both in our 20s.” 

A couple months after they started dating, Leo took Allie to a Mumford & Sons concert in April 2013. They took a photo together, which Leo had framed for Allie to take with her to her final year of school. “I carried the framed photo with me to school, overseas on exchange, and then back home again,” remembers Allie. 

“Fast forward to February 2018, Leo and I moved in together and he handed me the photo to unpack, specifically asking me to open the frame. On the back of the photograph that I’d carried with me for nearly five years, he had asked me to marry him back in 2013 – I’d just never opened it up,” she shares. Leo then got down on one knee and asked Allie to marry him again, five years later. 

When planning their wedding, the pair aligned early on their goals for the celebration: to create an experience for their loved ones, and teamed up with wedding professionals based in Greece that helped them achieve their vision, including planning services provided by Julia & Evita and florals by Betty Flowers Santorini. 

“We were willing to go the extra cost and inconvenience if it meant that the weekend would feel like a giant thank-you card to the people we love the most,” smiles Allie. When selecting a venue, the pair chose Cavo Tagoo Santorini, where they had dined on vacation two years before the big day. “When we got engaged, we started talking about what we’d do if there were no limits and we both immediately shared the same dream location… We really couldn’t think of anywhere we’d rather be married!” 

“We wanted to incorporate Greek traditions given our heritage and the setting, while also having the evening feel modern and present.”

To honor their backgrounds, the day started with a traditional church ceremony. The bride was gorgeous in a strapless gown showcasing a sweetheart neckline; she carried a lush bouquet of white flowers with organic greenery. “Walking down the aisle will always be one of those snapshots locked into our memory,” notes the bride, “as well as walking out of the church into a crowd of all of our favorite people – and some tourists, who had paused by then too!” 

When selecting the theme of their reception, they focused on the setting. “We knew that the view and the venue were going to be the centerpiece,” urges the bride of their vision. “People had traveled so far from all over Canada, the US, and Europe to be there that we didn’t feel like we wanted to add any complicated theme layered on top of that.” Thus, their design scheme was Greek-inspired, with the blues, greens, whites, and additional colors reflecting the Cyclades Islands. In order to not block the sea and sunset, floral arrangements were kept low and accented with romantic candlelight. 

“We wanted to incorporate Greek traditions given our heritage and the setting, while also having the evening feel modern and present,” shares the bride of the unique additions. Each place setting showcased a Greek “evil eye” that guests could take home with them, seating charts and other paper goods designed by Miss Design Berry were adorned with Greek typography, olive-branch greenery was displayed on tablescapes, and of course, Greek dancing was enjoyed all night. 

Though the day itself was picture-perfect, Allie and Leo’s focus on their guests extended past the wedding day. To ensure their loved ones were filled with special memories for the entire weekend, the celebratory festivities were not over. The next day, a laid-back beach day allowed the couple and their guests to spend time together in a relaxed, beautiful setting, before the newlyweds departed on their honeymoon to continue their travels in the Cyclades Islands, enjoying Folegandros, Sifnos, and Milos.

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