Old San Juan Engagement Photo Session with Daysi & Bryce

Jun 28
2 min read

Welcome to our fun Old San Juan Engagement Photo Session with Daysi & Bryce. As a wedding photographer, there is nothing quite like the magic of exploring historic cobblestone streets with a couple who is completely, effortlessly in love. Daysi and Bryce have already booked me for their upcoming wedding, and after spending an afternoon capturing their love story shoot, I absolutely cannot wait for their Old San Juan wedding day to arrive!

For their session, we set out to capture the timeless texture of the charming colonial Old San Juan, blending iconic historical landmarks with some of the city's most beautiful spots.

Couple holding hands crossing the street in old San Juan with a beautiful and huge pink building behind them

Old San Juan Engagement Photo Session with Daysi & Bryce.

Strolling Down Calle Luna

We actually kicked off our morning walking down my personal favorite partially carless street, Calle Luna. There is something incredibly peaceful about the stretches of this street where parked cars don't crowd the frame early in the day. It allowed Daysi and Bryce to just hold hands, walk, and take in the unique atmosphere. The pastel facades and charm of Calle Luna provided the perfect, relaxed setting to start the first chapters of their love story shoot.

Couple staring into the horizon at calle Luna in Old San Juan, Puerto Rico softly smiling

Smiling couple enjoying the streets of Old San Juan

Couple crossing the street in old san juan enjoying their vacation and their engagement session

Wandering Caleta de las Monjas

Next, we headed to one of the most popular streets in Old San Juan for photos: Caleta de las Monjas. Known for its cuteness, colorful colonial architecture, wooden doors, and beautiful natural light cascading between the buildings, it’s a photographer's dream. Daysi and Bryce brought so much joy and energy to the space, making it easy to capture authentic, candid moments against the stunning, bright backdrops.

Newly engaged couple, wearing sunglasses because of bright sunlight posing in front of a white colonial building

A Coffee Break at Materia Prima (Hotel El Convento)

After walking the cobblestones, we took a little intermission to relax and recharge. We decided to stop by for coffee at Materia Prima's mercado in Hotel El Convento. It was the perfect spot to cool off, chat about their wedding details, and catch some beautiful, casual lifestyle frames of them just enjoying their drinks in such a stunning, historic setting.

Engagement ring and hand holding witht a silver and gold watch

Bryce and Daysi enjoying a coffee break at Materia Prima at Hotel El Convento in Old San Juan. Daysi, smiles at her boyfriend.

Portraits at an iconic garita at Plaza de la Rogativa

To bring our session to an unforgettable close, we headed over to the sweeping cliffs overlooking the dramatic bay at Plaza de la Rogativa. Daysi and Bryce had a few specific locations in mind that they really wanted to feature in their gallery. The couple specifically requested photos inside a garita (the historic sentry boxes built into the fortress walls), which offered the perfect, dramatic framing for some intimate portraits. The sweeping ocean views mixed with the rich history made for an incredible, grand finale to their morning.

Getting to know Daysi and Bryce before their big day was such a joy. If their energy during this session was any indication, their upcoming wedding is going to be absolutely spectacular. Stay tuned to the blog to see their wedding day gallery soon!