Ray and Teresa

Proposal Ideas Santorini, Greece

How We Met

Ray and I met a couple of years ago through a mutual friend. Having known each other even back from high school, we knew who each other were, never interested until forced into a first date. Ray’s best friend was dating my friend and his best friend, Joe, was very persistent in hooking the two of us up. Now if you were to ask Ray, Joe didn’t have the best track recorded with hooking him up with these “dates.” Hesitant, both him and I, we both agreed to the “blind” date.

Ray's Proposal in Santorini, Greece

(A little side note, I was NOT a fan of Ray, knowing him from high school, I for whatever reason hated him, but little did I know..) Our first date was a concert, Old Dominion, one of my favorite bands. Shy at first, we ended up warming up to the idea of each other and actually having a really good time. Ending with a drunken Uber ride home, not sure when we were going to see each other next, we kissed and left it at that. A couple of weeks later, we were booking our first vacation together and have been inseparable ever since.

How They Asked

Since Ray and I started dating, everyone could tell we were, as cliche as it is, destined to be together. I was technically his first girlfriend and everyone knew, I would also be his last. Since we started dating, adventures and traveling have always been a huge part of our relationship. So without realizing it back then, a destination engagement has always been in the cards.

Ray and I planned a trip to Greece, on a whim actually. We enjoy seeing new places and exploring new things, so why not Greece? We booked our flights, arranged our Air BnB’s and anxiously awaited our next adventure. Little did I know the biggest and most memorable adventure of them all.

Marriage Proposal Ideas in Santorini, Greece

The time was here, we were making our way to Greece, a long 9-hour flight from New York. We first arrived in Athens, spent a couple of days exploring there and then headed to Santorini on a short, half-hour flight. When we arrived in Santorini, we were greeted by not one but two “Mr. Raymond” signs. We had previously arranged a transport with one of our tour guides, not knowing the hotel had sent their own. But to our surprise, November is considered the off-season for Santorini so many places close at the end of October, including our hotel. A blessing in disguise, the transport service was scheduled to pick us up and bring us to a new hotel, arranged by the previous hotel. With much confusion, exhaustion and frustration, we went with the hotel’s transportation. After what felt like an hour of winding roads in pitch black, we made it to our hotel, safe and sound.

Wedding Proposal Ideas in Santorini, Greece

The two of us were frustrated and exhausted but also scared because of so much unknown since getting off the plane. We were ready for bed, hopeful to start over the next morning having arranged a wine/island tour for the first full day on the island. On Sunday, we woke up, had breakfast on the balcony and were feeling much more relaxed. After we both had gotten ready for the day, I could tell something was off with Ray. He was pacing around the room, being very short with his words and he truthfully had almost stopped breathing. Without my thought, just thinking he was still trying to relax from the night before, I let it go. Finally ready, Ray had asked me to go out on the balcony to take a picture.

He set up the iPad with a 10-second timer. The first photo came out perfect but Ray said let’s take another just to be safe. As he set up the iPad and timer, he came to stand next to me again but instead he said, “Teresa?” And then got down on one knee, as I heard a crowd of people cheering for us above, I also heard myself yelling “no, no, this isn’t happening!!” With my heartbeat in my ear, I looked down at Ray and saw in his hand a small wooden box that said, “Be With Me” lyrics to a song by Old Dominion, the concert we went to on our first date and then I finally heard him say, “will you marry me?” The iPad clicked, I screamed ‘yes’ and the crowd whistled and yelled, it soon became the best moment of our lives!

We have been fortunate to celebrate our engagement all over Santorini. From one side of the island to the other, we’ve been able to take beautiful photos, lucky enough to have the most stunning background for a mini engagement photoshoot! From the sunsets and the bay to the blue and white buildings, our destination engagement has become our greatest adventure yet!

Engagement Proposal Ideas in Santorini, Greece

Special Thanks

 | Tour Guide / Took photos