Laura and Thomas

How We Met

High school sweethearts, I met Tom Romeo (yes, a last name fit for a fairy tale) in the springtime of our sophomore year of high school. We had 7th-period lunch together. He bought me a slushie from the cafeteria and the rest was history!

How He Asked

As high school sweethearts, we just celebrated our 10 year dating anniversary back in April – a decade of love and milestones. An engagement was on the horizon, but I just didn’t know exactly when he was going to pull it off. Tom had just graduated from the police academy a week prior to us going away on vacation. After 6 months of military-type training, he definitely needed a getaway to just relax and unwind before he started his dream job as a Police Officer, just him and I. So the excitement was already in the air.

Where to Propose in Aquinnah Cliffs, Martha's Vineyard

Marriage Proposal Ideas in Aquinnah Cliffs, Martha's Vineyard

Boston is our absolute favorite city. Living right by New York City, we love how cute and small Boston is compared to NYC and that you can easily walk from one end to the other. There’s just so much to see and do and being bored is not an option. The only other times we have visited Boston was in the winter, so we figured this would be the perfect trip to get to enjoy parts of the city we never could in the freezing cold weather. Being that it was summer, we wanted to fit in another place that we’ve never been to, Martha’s Vineyard, which was our first stop. It was a 4-hour ride to the Woodshole Ferry, where we hopped on to go over to the Vineyard. We immediately fell in love with it. We stayed in the cutest hotel, right on the inlet of Oak Bluffs Harbor. We spent the weekend indulging in lobster rolls and clam chowder, celebrating him finally getting his dream job.

When it came to our last night before heading over to Boston, we knew we wanted to get to a part of Martha’s Vineyard that is known for their sunsets over the ocean and the gorgeous cliffs that look right over the beach, Aquinnah Cliffs. And for us East Coasters, we don’t get sunsets over the ocean, so this was a must see for us. It was July 16th, and the whole day was super cute. We rented bikes and rode all around the island. We rode to the beach where you’ll find the infamous ‘Jaws Bridge.’ Taking the plunge, we both jumped off it and had a blast. We rode to Edgartown where we were going to go for dinner and walked around the little shops right along the water.

Aquinnah Cliffs were on the opposite side of the island from where we were staying so we decided to rent a jeep to get us to the cliffs. We went to a delicious seafood restaurant for dinner and sat at a table overlooking the water. It was a gorgeous summer night, not too humid and the perfect night for a breathtaking sunset. We ended dinner with just enough time to make it to Aquinnah. So we got in our jeep, took the top down and rode 30 miles west to the opposite side of Martha’s Vineyard.

Once we got to Aquinnah, there wasn’t much there, but a lighthouse, a little restaurant, some tourist shops and a spot next to it that overlooked the beach. It was GORGEOUS. I felt like we were in Ireland with greens everywhere, the red cliffs in the background and a slight fog over the ocean. Even though the view from the top was beautifully breathtaking, the whole point was to get down to the beach for sunset. So we found the walkway that took us down to the beach that was about 1/2 mile long. At this point, we were chasing the sun and racing against time.

We finally got down to the beach and quickly headed towards the sun where the beach was super secluded and no one was around us. Everywhere you looked was beautiful – the sun against the cliffs cast the most beautiful red and orange onto the rocks and the sun over the ocean was something like I’ve never seen before. It was the perfect photo op and we had brought a tripod with us for the convenience of it – little did I know it would come in very handy! We settled our things down and Tom set up the tripod right on the rocks that were on the beach. I ran to get into position as he did a test shot with the camera. “Perfect!” Tom said as we did one more photo and he ran over to kiss me. He went back to the camera to see how it came out and said, “Let’s do another one, look at how perfect the sun is setting over the water!” Waiting for him to set it up for the next picture, I turned around to just enjoy the sunset as it was just setting over the ocean. Little did I know, Tom carefully had made his way over to me, as I turned around and there he was on one knee with a beautiful ring in his hand! I couldn’t believe it! He completely surprised me. Even after a decade together, he still managed to wow me and pull off the most breathtaking proposal!

Proposal Ideas Aquinnah Cliffs, Martha's Vineyard

And I bet you’re wondering how that perfect photo came out? Well, instead of hitting the timer button on the camera, he had started recording it and got the whole proposal on video. Afterward, we had a little engagement photo sesh with the gorgeous cliffs in the background and the ocean waves crashing against the rocks. It was nothing short of perfect. Martha’s Vineyard became our new favorite place and I finally had my Romeo.