A Romantic Surprise Proposal in Boston’s Historic North End | Sam & Tess

Feb 22

There’s something magical about a well-planned surprise proposal, and Sam’s thoughtful approach to asking Tess to marry him was nothing short of perfect. He reached out to me with a vision: to pop the question in a location that held deep sentimental value—their very first apartment together, nestled in the heart of Boston’s historic North End.

To make sure we captured every moment discreetly, I brought my husband along to assist with behind-the-scenes footage and help us blend in as tourists. With a watchful eye on our couple, I stood ready for the big moment. Sam led Tess to the perfect spot, shared heartfelt words, and then dropped to one knee.

Of course, she said YES! The joy on their faces was undeniable. After Sam pointed us out, we shared warm congratulations, captured their first moments as fiancés, and explored the North End for more portraits. The neighborhood, with its old-world Italian charm, provided the perfect backdrop—the restaurant Ciao Roma on the corner, the stunning architecture, and the green-faded copper against red bricks all added vibrant pops of color to the winter scene.

Thinking of planning a surprise proposal? Here are a few tips to ensure everything goes smoothly:

Plan Ahead & Book Early – Reach out to your photographer as far in advance as possible. We’ll help you map out the best time, lighting, and location for your special moment.
Look Your Best – A proposal is a once-in-a-lifetime moment, so make sure you’re both dressed for the occasion. If you want to keep it a surprise, plan a nice dinner reservation nearby so there’s a reason to dress up.
Choose a Meaningful Location – Whether it’s where you first met, your favorite weekend spot, or even your first home together, picking a sentimental location adds an extra layer of romance to the proposal.
Celebrate Afterward – Want to make it even more special? Plan an intimate engagement party with family and friends or a romantic dinner to soak in the moment together.