When my brother Caidin told me he wanted to propose to his girlfriend Cidnee on the beaches of Vieques, Puerto Rico, I knew this would be a trip I couldn’t miss. Even though we hadn’t originally planned to visit Puerto Rico in 2025, the opportunity to photograph such a meaningful moment for my little brother was something I couldn’t resist.

Planning the Perfect Vieques Proposal Photography Session

Caidin had it all planned out. The proposal would happen during Cidnee’s birthday celebration, making the moment even more special. We arrived in Vieques and immediately began scouting beach locations together. Cidnee knew we were planning a photoshoot—after all, what better way to celebrate a birthday trip than with beautiful beach photos? What she didn’t know was that this session would end with a ring and a question that would change everything.

We chose Media Luna beach for the proposal, and it couldn’t have been more perfect. The beach was incredibly calm and peaceful, with gentle waves and soft sand creating an intimate atmosphere. As the sun began to set, we started taking photos. The anticipation was building, and honestly, it was clear Cidnee sensed something special was about to happen.

The Proposal Moment

Caidin and I had coordinated ahead of time—when I prompted him to pick her up and spin her around, that would be his cue. The moment came, he swept her off her feet, and when he set her back down, he dropped to one knee. The surprise, joy, and tears that followed were absolutely beautiful to capture. Watching my little brother propose was incredibly poignant and emotional. This is exactly why I love Vieques proposal photography—these raw, genuine moments against stunning natural backdrops. Engraved in her ring was the phrase “We Always Do”, a nod to “their” song, We’ll Make It Through by Ray Lamontagne.

After the proposal, we celebrated with dinner at Mango Taphouse, an amazing restaurant tucked deep in the woods of Vieques. We’d made reservations hoping to sit on the patio, but rain changed those plans. Still, the food was incredible and the celebration continued late into the night.

The trip was a huge success, and we later celebrated their wedding in October 2025 in Utah, making these proposal photos even more treasured.

Beach Proposal Photography Tips

If you’re planning a beach proposal or engagement session, here are some helpful tips:

Scout your location ahead of time. Visit during the same time of day you plan to propose to check lighting and crowd levels.

Have a backup plan for weather. Tropical locations can be unpredictable, so know alternative spots or times.

Coordinate with your photographer. Establish clear signals or prompts so everyone knows when the big moment will happen.

Keep it natural. The best photos come from genuine reactions, so don’t overthink poses before the proposal.

Consider the tide schedule. Low tide often provides more beach space and interesting elements like tide pools.

Ready to plan your own unforgettable proposal? Whether you’re dreaming of a beach engagement or another stunning location, I’d love to help capture your special moment. Contact me to book your own proposal or engagement session today.