Planning Old San Juan Engagement Portraits

Old San Juan is the most popular location for engagement sessions in Puerto Rico. Its history, breathtaking viewpoints and colorful architecture make it one of the most sought after, characteristic photo spots in the island. When planning your couple, anniversary or engagement, there’s a few things to consider.

Tips for your Engagement Photos in Old San Juan

1. Get ready to walk for variety

   Don’t underestimate the old city! A common misconception (influenced by Googlemaps) is how much time it takes to get from one spot to the other. Distances look short, but Old San Juan feels a lot bigger. There’s quite a few ‘uphill/downhill’ streets and uneven terrain. You can easily spend an hour taking photos from El Morro Fort to nearby Calle San Sebastian (and that’s not the southernmost point).

2. On that note: wear comfy shoes!

   If your ‘photo shoes’ aren’t comfortable enough to be worn continuously, wear sneakers instead and change them after moving from spot to spot. Those uphill streets I just mentioned? Plus cobblestone streets? And some rocky, slippery areas in the forts? Not great for heels if you love your feet.

3. Expect cats, more cats and tourists

   As your photographer I will take you to the more secluded areas, but running into cats in Old San Juan is inevitable. Old San Juan has a cat colony (check out Save a Gato who helps spay and care for them) and at least one will photobomb you.   Don’t worry — they’re friendly and used to people by now. You might consider bringing along allergy medication if you have an extremely severe reaction to them. Also, Old San Juan is popular. You will also run into tourists and friendly locals.

4. Don’t choose a Sunday

   Have your session on a weekday. I understand travel plans have to be worked around with, but if you can avoid it don’t schedule your engagement photos for Sunday. It’s the most popular day for locals to visit Old San Juan, which means traffic delays, difficult parking. A weekday offers a less crowded experience and more privacy to be lovey-dovey with each other.

5. Have fun with it!

   There’s a lot you can do in Old San Juan besides walking and watching the sunset. Perhaps try a piragua for the first time during your shoot, or our famous piña coladas.

Here’s a couple that definetly had fun with it: Maria & Dave. Their engagement session in Old San Juan was full of great energy!