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Surprise Anniversary Session in Old San Juan

I’m so excited to share this surprise anniversary session in Old San Juan with you today! Why? Well, it’s me! And my husband of 23 years. We recently went on a Windstar Cruises Caribbean adventure, and we left from Puerto Rico. We haven’t had photos done in years, so I surprised my sweetie with an anniversary session and our first Airbnb experience (see here). I love the results!

Surprise Anniversary Session in Old San Juan Puerto Rico | Hill City Bride Destination Wedding Travel Blog

Yes, I will admit that a tiny bit of me feels a bit odd posting photos of myself on the blog, but I thought – why not? All love needs to be celebrated, even if it is mine. Plus, the backdrop of historic Puerto Rico is just so lovely with the gray-bluish brick walkways, detailed buildings and stunning views.

I also would like to say a little about hiring a destination photographer. It was a little scary in a way because I usually know photographers personally, but hiring one from a distance is a bit challenging. So, finding a photographer in San Juan actually took some sleuthing. Of course a Google search helped, and I also tested out a few hashtags on Instagram. I culled down the photographers based on two things – their style of photography and the look of their website (judgy, maybe, but I feel that photographers are in the business of visual arts, so the site matters).

After emailing a few about availability and pricing, I ultimately chose one based on the fact that he was friendly AND he saw my email address and took the time to check out my website. I truly appreciated that, so Gabriel Gonzalez was the top pick in my book. He was professional, knew Old San Juan really well, and made both Earl and I feel at ease during the session. I love the results!

So, take a peek at our anniversary session in Old San Juan today!

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And last, but not least, my favorite set of photos. I love you, Earl, and I am looking forward to more of life’s journey with you. Here’s to another 23  years!

Surprise Anniversary Session in Old San Juan Puerto Rico | Hill City Bride Virginia Wedding Blog Travel by Gabriel Gonzalez Photography Destination

Surprise Anniversary Session in Old San Juan Puerto Rico | Hill City Bride Virginia Wedding Blog Travel by Gabriel Gonzalez Photography Destination

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  • Alex R - Beautiful pics . Congrats 🙂

  • Jennifer - Thank you so much! It was a lot of fun. <3

  • Amiekay - First: Happy Anniversary! You two look so happy and in love. 🙂

    Second: I love Old San Juan! These photos really capture the beauty of the city and make it feel appropriately romantic. I love that the photographer went the extra mile too to check out your blog! That’s the way to make yourself stand out from the crowd for sure.

  • Jennifer - That is all so sweet! And yes – he was such a nice photographer. I’m so happy with the results. <3

  • ANITA ZYCH - Beautiful website

  • Nathan - Lovely photos, you guys look so cute together! Looks like a great anniversary you had 🙂

  • Jennifer - Thank you so much! We really did enjoy our timee. <3

  • Jennifer - Thank you so much, Anita! Sometimes I think about changing it, but I really do like it. <3

  • Tahnee - This is cute and you got some great pics!

  • Jennifer - Thank you so much! I love them. <3

  • John - Gorgeous couple! Congratulations to both of you! And by the way, the images are amazing! Beautiful photography!

  • Jennifer - Aw, thank you! I was so excited to find a photographer that was just our style from afar. <3

  • Laurence - Great pictures!

  • Karla Dela Rosa - Congratulations on your anniversary! Totally in love with your photos! So romantic and gorgeous!

  • Megan - Ohhhh this is just so darling! I’m so in love with these images. They are dressed so adorably for this too 🙂

  • Czjai Reyes-Ocampo - Aww, such a lovely couple made even lovelier by the stunning backdrop. My favorite photo is the one with the flowers in the foreground – very romantic. 🙂

  • Elizabeth O - What a lovely idea, these photos are so lovely and they look very in love.

  • Jennifer - Thank you! I was really happy with the photos, too. <3

  • Tara - I LOVE these photos, they’re so timeless! many congrats to you both, wishing you all the happiness!

  • Lisa Rios - The scenery looks so beautiful and you two are the cutest couple! Wishing you may more happy years together.

  • Carina - Happy Anniversary! Well done to the both of you- congratulations! Your outfit is beautiful and the scenery is breathtaking. Really enjoyed reading your post and perusing your pictures 🙂

  • Jennifer - Thank you so much!! 🙂

  • Jennifer - Thank you! We had a great time, and I’m so glad we scheduled a session. 🙂

  • Candice - Oh wow that place is beautiful! I love all the photos!

  • Esme Sy - Now this is what I call an ageless milestone, something celebrated between two loving people flourished with the romantic ambiance of a beautiful place like Old San Juan. I could stare at your pictures all day long if that wasn’t going to be a bit weird!

  • Alina - What a wonderful idea for a surprise, and congratulations on your anniversary. 23 years is an achievement! You look so beautiful together and so much in love. 🙂

  • Jennifer - Thank you so much!! 🙂

  • Heather McMechan - I can’t get over the way these photos turned out. So crisp and clean. Glad you two were able to enjoy the views in Old San Juan.

  • emma white - Oh wow! It looks and sounds as if you had an amazing time away and such beautiful pictures that you can treasure forever.

  • Monika - I want such a surprise anniversary too lol! Looks and sounds fantastic…<3

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