Some proposals feel like a love letter to the city that shaped a relationship, and Oscar and Deborah’s engagement at the top of the W Hotel Boston was exactly that. Oscar and Deborah first met while studying in Boston. They quickly fell in love, and over time, their relationship blossomed right here in the heart of the city. So when it came time to propose, Oscar chose a place that offered the perfect view of their love story: a rooftop overlooking the skyline of the city that brought them together.

As the sun began to set, Oscar got down on one knee and asked Deborah to spend forever with him. Her answer was a joyful yes. After the proposal, they stood together on the rooftop balcony, looking out over the city. They pointed out the places that marked their journey including the spot where they had their first date, the place they shared their first kiss, and so many meaningful memories in between.

To celebrate the moment, they did something they have been learning together. They practiced their salsa dancing as the sky turned the perfect shade of gold. It was romantic, personal, and full of joy.

It was an honor to photograph this milestone for them. Moments like this are why I love being a Boston proposal photographer. There is something so special about documenting the exact spot where a new chapter begins.

If you are planning a proposal with a view of the Boston skyline, or dreaming of a romantic sunset moment like this, reach out. I would love to help you capture it all.

Some love stories feel like they’re straight out of a movie, and Natalie and Aaron’s is one of them. These high school sweethearts have been growing together for years, and when Aaron decided it was time to propose, he chose a place that held deep meaning—Boston, the first city they ever lived in together.

With the help of The Yes Girls, a luxury proposal planning team, Aaron put together the most romantic sailboat proposal in Boston Harbor. He chartered a private boat through Classic Sail Boston, and the gorgeous floral installation by Soulmate Florals made everything feel magical from the moment Natalie stepped on board.

As the sailboat drifted along the water, the golden light hit just right and the stage was set. Natalie was completely surprised. From the peaceful sail to the thoughtful decor, every detail led up to the moment Aaron got down on one knee.

The proposal itself was so joyful and emotional. You could feel their love instantly. The way they held each other, the huge smiles, and the deep hugs—they were completely in their own world. It was one of those moments that reminded me why I love photographing proposals. Capturing such genuine emotion in such a stunning setting is truly an honor.

Whether you’re dreaming of a Boston sailboat engagement, planning a surprise proposal, or looking for ideas to make your moment unforgettable, this session is the perfect inspiration. Natalie and Aaron’s story is proof that personal touches, thoughtful planning, and a meaningful location make all the difference.

Boston Proposal Vendors
Proposal Planning: The Yes Girls
Sailboat Charter: Classic Sail Boston
Florals: Soulmate Florals

Last week, I had the incredible honor of photographing Varun and Elisha’s surprise proposal at Christopher Columbus Waterfront Park in Boston. It was one of those magical days where the snow fell in big, fluffy flakes, blanketing the city in a winter wonderland. It felt like a scene straight out of a Hallmark movie, with people playing in the snow and walking their dogs nearby.

Varun had worked with the amazing team at The Yes Girls to plan every detail of the proposal, and the stunning floral arrangements by Table and Tulip added a romantic touch to the already dreamy setting.

When Varun and Elisha arrived at the park, her reaction was priceless. As soon as she saw the setup, she was completely surprised and shed happy tears—it was such a heartfelt and beautiful moment to witness. Varun even planned a thoughtful game as part of the proposal. He laid out photos from the course of their relationship, and Elisha had to put them in order from oldest to most recent. It was such a creative way to relive their journey together before asking her the big question.

Elisha said yes (of course!), and their joy was contagious. They were such a sweet couple, and capturing this once-in-a-lifetime moment for them was a privilege. Even though I was freezing, watching their love story unfold in real-time made every second worth it.

Moments like this are why I love my job so much. Photographing proposals, weddings, and engagements allows me to freeze these meaningful memories in time, and being a part of Varun and Elisha’s snowy love story is one I’ll never forget.

To Varun and Elisha, thank you for letting me be part of this milestone in your lives. Wishing you both all the happiness in the world as you begin this new chapter together!

Samantha and Stephen’s Boston engagement session was the perfect blend of fun, spontaneity, and genuine moments. We started early in the morning in the heart of Boston, before the city had fully woken up. With the quiet streets and iconic Boston landmarks as our backdrop, it felt like we had the entire city to ourselves, creating the perfect atmosphere for this engagement photography session.

Right from the start, it was clear how laid-back and easygoing Samantha and Stephen are as a couple. Their chemistry made this engagement shoot feel effortless, with natural moments of laughter and joy replacing any stiff posing. As we wandered through Boston, we stumbled upon a local donut shop, and without hesitation, decided to pop in. This spontaneous stop gave us some of the most memorable photos, showcasing their fun-loving personalities and genuine connection.

Capturing these candid moments during their Boston engagement photography really highlighted why I love doing engagement shoots—it’s not just about perfect poses, but about preserving real memories that reflect who the couple truly is. For Samantha and Stephen, that meant donuts, laughter, and exploring the city they love.

If you’re looking for Boston engagement photographers or planning your own Boston engagement photos, let’s connect! Sessions like these are all about creating a relaxed, enjoyable experience that tells your love story in the most authentic way. I’m beyond excited to also be photographing their wedding next summer, and I can’t wait to capture the next chapter of their love story!

Love is a beautiful journey, and there’s no better way to immortalize it than through the art of photography. If you’re planning to tie the knot in 2024, I have exciting news for you! I am thrilled to announce that I am now booking weddings for the year 2024. Whether you’re envisioning a romantic, intimate elopement or a grand celebration with hundreds of guests, I am here to help you capture every precious moment of your special day. I am Boston and New England based, but always willing the travel 🙂

Why Choose Rachael Shek Photography for Your 2024 Wedding?

1. Experience and Expertise: With years of experience in wedding photography, I am well-equipped to handle all the unique challenges and moments that come with the territory. From the quiet, heartfelt exchanges to the joyous bursts of laughter and the tear-filled vows, I’ve seen it all and am ready to document it beautifully.

2. Personalized Service: Your wedding day is as unique as your love story. I believe in getting to know you as a couple, understanding your preferences and style, and tailoring my approach accordingly. Your wedding photographs should reflect your personalities and the essence of your relationship.

3. Stunning, Timeless Imagery: My goal is to create images that will stand the test of time. Whether you prefer classic elegance, a modern aesthetic, or a blend of both, I have the skills and creativity to deliver photographs that you’ll cherish forever.

4. Attention to Detail: I understand that planning a wedding involves countless details, both big and small. Rest assured that I will be there to capture every detail you’ve put so much thought and effort into, from the intricate lace on your dress to the delicate floral arrangements.

5. A Relaxed and Fun Experience: Your wedding day should be stress-free and enjoyable. I pride myself on creating a relaxed and fun atmosphere that allows you to be yourselves. Candid moments and genuine smiles often result from a comfortable and joyful environment.

6. High-Quality Products: Beyond capturing your day, I offer a range of high-quality products, including albums and prints, to help you relive your wedding day and share your memories with loved ones for generations to come.

How to Secure Your 2024 Wedding Date

Booking your wedding photographer is an essential step in planning your 2024 wedding. Here’s what you need to do to secure your date with me:

1. Reach Out Early: The earlier you contact me, the better chance you have of securing your desired wedding date. Popular dates tend to fill up quickly, so don’t delay! The best way to inquire is here!
2. Schedule a Consultation: Let’s get to know each other! We’ll schedule a consultation to discuss your wedding plans, your vision, and your photography needs.
3. Sign the Contract: Once we’ve found the perfect package for you, I’ll provide you with a contract to sign. This contract outlines all the details of our agreement and ensures that your date is reserved exclusively for you.
4. Engagement Session: If you’d like, we can plan an engagement session to get comfortable in front of the camera and create some beautiful pre-wedding memories.
5. Stay in Touch: Leading up to your wedding, we’ll keep in touch to go over any final details, timeline, and special requests to ensure everything runs smoothly on your big day.

I can’t wait to be part of your 2024 wedding journey and help you create stunning memories that will last a lifetime. To inquire about availability, pricing, and to schedule your consultation, please reach out to me through the contact information provided on my website. Let’s make your 2024 wedding unforgettable through the power of photography!

Remember, your love story deserves to be told, and I am here to tell it through the lens of my camera.

Let’s tell your story,

Rachael

I went to school on the North Shore, and something that I’ve always missed since I graduated were the sunrises on the beach. Whenever I was stressed, happy, or just needed something to do, watching the sunrise or sunset on the beach was always a go-to option. When Nathan asked me to shoot a surprise proposal for him in Beverly, Massachusetts, I didn’t hesitate to say yes. I’ll take any excuse to shoot a proposal in a lovely place that will always feel like home.