Behind the Scenes in Puerto Rico | Vieques & Old San Juan

Last year I had the honor of photographing Anna and Andy’s wedding in Vieques, Puerto Rico. Matthew came with me as my assistant, as he does with my larger and more distant weddings. I’m usually a solo photographer, but when traveling far or working over several days, it is a blessing having someone to help with bags, light set up, and as an extra set of hands. I spent a lot of time editing the various photo shoots we had on the island that I never got around to editing our personal behind the scenes photos from the trip. I finally have the chance to share them with you.

We flew from Bradley International Airport to San Juan then took a small plane to the little island of Vieques. We were the only two passengers on the little plane. I felt like a movie star on a private jet off to paradise. Matthew on the other hand, felt very differently. Not very used to planes, when we were approaching for landing the small plane stalled and dropped pretty far from the sky. I was confident that our pilot, Angela, would be able to right our orientation. Matthew was not so confident. He was silent the entire time at the airport and taxi to the hotel. When we made it to the room he flopped face first onto the bed claiming, “We almost just died!” and would not get up. 

I told him, the pilot has made this trip hundreds of times before. We did not almost die. “Yes, we did. We almost died.” It took a bribe of food to get him out of the room and into the island sunshine. We stayed at Banana’s guest house right across from the beach. It was also a great restaurant. While there I discovered my love for a new dish: mofongo (a Puerto Rican dish of friend mashed plantains). I love trying new foods, especially she I travel. Our guest room had a very local and island vibe:In the mornings I would get up early and sit at the counter overlong the water to edit photos. The best way to start a working day.On the job. The day of the wedding, the guys started off the day skeet shooting. I had just come back from yoga on the beach with the ladies and Matthew was able to join the gents. The day before the wedding we celebrated with a pig roast on the beach. I took a lot of photos of the festivities and some great wedding guests took a few photos of Matthew and I together. Matthew proposed while we were on the trip! Our engagement story is a funny one because Matthew had planned out several proposals that were all thwarted. He brought the ring with him just in case he found the right moment and he did. This is the exact spot where he proposed at sunset:During the trip we had so many great experiences with the amazing guests at Anna and Andy’s wedding, their wonderful family, as well as exploring on our own. We had wonderful food, kayaked in the bioluminescent bay at night, and went on a kayaking and snorkeling tour on the island. The morning after the wedding we photographed a glam-the gown session around the island and said farewell to Banana’s guest house. We had another plane to catch. Did I mention that on the way back I was asked to sit in the co-pilot’s seat? Dream come true! The other passenger’s on the plane laughed at my excitement. The pilot was a woman around my age named Annie. I told her how much I love planes and that I want to fly a plane one day. She looked at me warily and told me “just don’t touch anything, ok?” With time to spare before our early morning flight back home, we checked in our luggage at the Hilton Caribe hotel in San Juan and took a taxi to old San Juan to explore. It was a stunning old city! All the buildings were painted bright colors that complimented the tropical landscape. Kitty cats were everywhere, just like there had been dogs and wild horses everywhere on Vieques. For dinner we found this gray place with a courtyard. We were the only ones in the court yard for a while before we were joined by a very amourous Swedish couple. Still some time to spare before the plane, we walked around the large hotel and rested in the hammocks along the beach. We arrived home to Connecticut to a snow storm. Goodbye tropical paradise, hello snowy New England.