Looking for amazing proposal ideas? Take a cue from this incredible Lisbon proposal and plan a proposal full of surprises!

We are absolutely blown away by the proposal Rueben planned for his now-fiancée Milica. He came up with so many surprise proposal ideas that the proposal itself was only one small part of the incredible surprises in store for Milica! Read on for the details and maybe you’ll feel inspired to plan your own perfect destination proposal?


We met in Chicago three years ago in an elevator of the apartment building we both lived in! Casual conversation turned into spending time together and we were able to develop a strong initial friendship, which later turned into a relationship. Our relationship flourished through our mutual love for travel and outdoor activities, such as hiking and skiing. We knew that we had found perfect partners in each other after we spent a month travelling Europe together without any hiccups.


My family had planned a trip to Portugal and Spain. We had always heard Lisbon was a fantastic city to visit. I wanted to capture the charm and culture of the city, as travelling and experiencing new cultures is our passion. Looking at example shoots in Lisbon from Flytographer really confirmed my decision to pull off the proposal here!


I wanted to make the day extra special for Milica. Since she is very close to her family, I knew I could not propose to her without her family being there! We were already in Lisbon with my family (my parents, sister, brother-in-law and nephew), so I pretended that we were going on a walking tour that my sister had reserved for us prior to dinner. Once we arrived at the fake meeting spot for the walking tour at Portas do Sol, Milica and I went to the viewpoint to take some pictures. We asked a friendly tourist (who just so happened to be Orsi, our photographer) to take some pictures for us. When she handed the phone back to Milica to check the pictures, I got down on one knee to propose. Orsi captured the moment brilliantly and Milica was completely surprised.

To add to the surprise, my family and my new fiancée then walked over to Castelo de São Jorge for more engagement photos, only to be surprised by Milica’s parents who had flown in that morning from Wisconsin. More joyful tears ensued!

Finally, I added in one more surprise as Milica’s sister and brother-in-law were waiting within the castle walls with some wine ready for us! Milica was completely shocked with all three surprises and was elated that both of our families were there to celebrate.