Kaleya and Brandon

How We Met

Back in 2014, I went to my best friend’s wedding tailgate so that the entire wedding party could meet for the first time which was at a baseball game. Kaleya was a guest of the bride’s cousin. Before the game started it began to rain, and I was wearing a bucket hat, so being the gentleman that I am, I offered her my hat. We exchanged numbers, and the running joke was that I would get my hat back. A couple of years later I slid into her direct messages and from that point, we’ve been dating ever since.

Where to Propose in Santorini, Greece

How They Asked

Background Story: Well, our family was planning a vacation to Greece this summer. We were planning to travel to Athens, Mykonos, and Santorini. I’ve known for quite some time that I was planning to propose to my girlfriend, Kaleya, but wasn’t sure when, where and how. So, it was after my brother Jordan mentioned the idea of the grand gesture of proposing in Greece. After searching through social media and internet posts, I was set to propose in Santorini, Greece.

Marriage Proposal Ideas in Santorini, Greece

I found and reserved a photographer, Kimon from the popular site “Flytographer.” At that time, I began clueing in all involved parties including, my mom, brother, her mom and cousin about my proposal plan, since they will all be traveling to Greece and taking part of the actual proposal. We had to make sure to be extra careful because Kaleya is very inquisitive about plans and details.

Proposal Ideas Santorini, Greece

So, as for the setting of the actual proposal. Sunday, June 30th the plan was for the entire family to wake up at 5:00 AM and be driven to Imerovigli, Santorini for a sunrise family photo shoot coordinated my brother, Jordan. The plan was for the entire family to wear coordinating outfits (All white, with touches of blue and red).

Kaleya's Proposal in Santorini, Greece

After having a meeting with my proposal concierge and photographer, we came up with a plan that Kimon will arrive at the proposal site 10-15 minutes prior to us. He staged himself as a tourist that was traveling alone and was trying to take an amazing “selfie” with the breathtaking Santorini views. As we walked down the long winding path, Kaleya, her mom and my brother were the first to arrive at the platform. Note: As they are walking, Kaleya mom’s asked my brother, “Hey, Jordan is that our photographer down there?” Jordan was able to play it off as Kaleya corrects her mom and says “Mom, Jordan is the photographer.”

As Kaleya walked towards the photographer (who is pretending to be a tourist), she joked around and said: “Oh are you our photographer today?” Kimon played it off smoothly as well and said: “Oh I’m just trying to take a selfie and can’t get my lighting right, do you mind taking my picture?” Obviously, Kaleya obliged and took a great picture (it’s all about those angles). As the entire family gathered with coordinating outfits, Kimon asked if we wanted him to take pictures with one of our cell phones, which we did.

After a few pictures on the cellphone, Kimon then brought up that he is a local photographer on the island that is needed to add to his portfolio. He offered to take some professional shots and email them to us later.

So, as we are killing this shoot. When Kimon asked us, “Do we have any couples within the couple?” My family looks around and points to us. Kimon begins to take photos of me and Kaleya. Once Kimon says that magical phrase, “Now, Let’s get romantic!”, which was discussed between him and me on our telephone conversation. That is the queue for me to propose. She was completely surprised and blown away (and not because it was super windy that day). Right after that, I surprised her with a surprise engagement photo shoot on the island. The day was completely perfect and went off without a hitch. Now, I can’t wait to spend the rest of my life with the girl of my dreams.

Engagement Proposal Ideas in Santorini, Greece

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Special Thanks

Kimon Kaketsis
 | Photographer