Couple: Alex & Allison
Location: Star Island, NH
Date: 7/13/25

This proposal was such an adventure! Alex reached out to me last summer to ask if I’d be up for capturing an undercover proposal during a boat tour of the Isles of Shoals, with the big moment happening on Star Island, NH. Heck yes! I’m always on board for a proposal with stunning ocean views and an amazing couple.

Alex and I spent some time on the phone talking through logistics, especially since neither of us had been there before. The boat tour was beautiful! It started off SO foggy, but the sun came out by the time we landed on the dock at Star Island. I tried my best to sneak a few pics of the two of them while Alex and I pretended I was just another tourist. Once Alex got down on his knee, I sprang into action! I love capturing the moment where everything was revealed to Allison, and I got to introduce myself for the first time.

Our time on the island was limited by the boat schedule, so we made the most of every minute we had. Star Island has so many gorgeous spots that it was easy to wander and capture beautiful photos at every turn. We were so caught up in post-proposal bliss that we nearly missed the departing boat (whoops!) but it was totally worth it. Some of my favorite images from the session were taken just before we headed back!

The boat ride back was the perfect way to wrap things up. We got to relax, chat, and finish the session with a few photos onboard. The Granite State Whale Watch crew was incredibly kind and even let us take a few extra photos after the tourists had departed, which we all really appreciated.

Before we dive into the photos, I thought it would be fun to have Alex & Allison answer some questions about the proposal! :

Alex: What inspired you to plan your proposal during the boat/island tour? 

“The plan I made was because Allison loves the water, so I figured an island would have plenty of it! Allison and I both went to UNH, and Allison lived on the Seacoast a bit after college as well, so the area is in our histories.

I wanted to do something that could be uniquely New Hampshire-esque for us, since we also both grew up here. What better way than enlisting not only you, Sierra, but the intrepid crew of the Uncle Oscar to accomplish a successful proposal!”

Alex: What was the most challenging part of planning the proposal?

“The most challenging part of the proposal planning phase was actually being able to scope out the island for a good spot to propose. Due to scheduling and bad weather on the weekends, I actually never made it out to the island beforehand – I ended up having to wing it! Thankfully Sierra took the time with me to go sleuth on Google maps for satellite and visitor images to scope out a spot we thought would work!”

Alex: Can you share about what makes the ring special / why you chose it?

“The ring I commissioned is special because I’m all about trying to express myself while remaining as unique as possible, so that Allison could have something that’s truly hers and hers alone. I went to many jewelers in southern NH, but Jackie from Hobbs Jewelers in Peterborough helped me (excitedly!) once she knew how much I was putting into it.

The style I chose is called a Toi et Moi ring, which means “You and Me” en Francais. To further symbolize this, she has one stone from her grandmother’s ring (the round) and one I had her pick out herself (the pear; without knowing the why, when, and how about it) on a platinum band. I wanted it to symbolize who she is, how far she’s been and where she’s come from, and the future she has with me.”

Allison: How surprised were you & what were your first thoughts when you realized what was happening?

I knew that Alex had a special weekend planned and I knew that he would go above and beyond because that’s how Alex is – he is always very thoughtful, romantic, and attentive to the small details. Even knowing that, I was still so surprised. Taking a trip out to the Isles of Shoals, proposing in the gardens overlooking the ocean and secretly planning our entire engagement shoot surpassed every other surprise Alex has ever planned (and he had set a high bar for himself already!) My first thought when I realized what was happening? “Oh my gosh, I am the luckiest girl in the world!” It really was the most beautiful and special day I could have imagined. I’m so happy that we have such beautiful photos to look back on this moment.

Both: Now that you’re engaged, what are you most excited about for this next chapter together?

Alex: “The next chapter I think we’re most excited about is moving into our new home and thinking about not only our upcoming wedding, but all the things we will accomplish in life together side by side. Her and me. 🙂 The possibilities are endless and our future is so bright!”

Allison: It’s been really amazing to enjoy this new phase of being engaged and being able to share our happy news (and beautiful photos) with our loved ones! This is such an exciting time for us and we have so much to look forward to in our lives together – our engagement and wedding are just the beginning of our story!

Photography: Sierra Does Photos

Isle of Shoals & Star Island Tour: Granite State Whale Watch

Ring: Hobbs Jewelers