Best Beach Proposal Ever – Surprise Engagement in the Florida Keys

A romantic surprise engagement photoshoot set up by the lucky groom-to-be! Looking for ideas for your upcoming beach proposal? Wondering how to coordinate with an engagement photographer to catch the moment on camera? Take some inspiration from Tyler, read on!

Surprise Engagement Photoshoot

Tyler knew that he wanted a romantic beach proposal for Spencer, and knew he wanted it to be a surprise, so he started laying the groundwork early. First, he set up the diversion (an important part of pulling off the surprise)– and planted the seed in his girlfriend’s head that there was a delay with the jeweler, and she wouldn’t be getting a ring for another couple of months.

Then, he enlisted the help of a trusted friend, as many proposers do. Stephanie wanted her best friends to have the perfect engagement, and was kind enough to connect me and Tyler! After all, there was never any doubt that this magical beach proposal had to be caught on camera. We started planning weeks in advance– picked the venue, the timing, and crafted the perfect story to feed Spencer so that she wouldn’t suspect a thing.

surprise proposal on Key West, Florida

Surprise Proposal Video

Once these North Carolina natives had arrived in Key West and settled in, that Saturday afternoon, they started getting ready for their romantic dinner cruise. Spencer LOVES taking photos to commemorate special occasions, so she was 100% down to dress up for their post-sunset dinner and enjoy a sweet walk on the beach beforehand. Little did she know, I had already scoped out the perfect spot for the proposal all the way on the western tip of the island, and Tyler was gearing up for one of the biggest moments of his life. (No pressure!)

My partner/assistant/sherpa extraordinaire and I staked out our spot among the unsuspecting picnic-goers near the water’s edge and reviewed the plan between ourselves and via text with Tyler. Everything was in place! We were so ready and excited for their arrival!

Surprise engagement photographer - romantic engagement photos

Beach Proposal!

Tyler kneeled, Spencer squealed, and I came out of hiding to photograph the happiest couple I’ve ever had the pleasure of working with. Their smiles only grew as the evening went on, the shock wearing off and leaving nothing but pure joy! By the time we finished shooting right after sunset, my cheeks hurt from smiling so much, and I wasn’t even the one in front of the camera!

Cute couple smiling after surprise proposal
woman admires her ring after a surprise proposal

We had some fun showing off the bling first…

woman shows off her engagement ring
Surprise Engagement Photoshoot

The surprise proposal turned into a surprise engagement shoot, and by the time the sky had turned dark and it was time for Tyler and Spencer to go enjoy their dinner cruise as fiancés, we all left as friends.

man, woman, sunflare, boat, key west
man and woman hug at their engagement photoshoot
all smiles at the best beach proposal ever!
Couple kisses at their engagement photoshoot
Man and woman smile and embrace after their engagement
Man and woman hold hands at their proposal photoshoot
emotional posing at engagement photoshoot
Romantic Sunset photos after surprise beach proposal
Oceanside engagement photo
Man and woman walk along beach after proposal
Man and woman kiss on rocks at beach in Key West, Florida
Artsy b&w photo of couple at their engagement photoshoot

Interested in planning your own beach proposal, or surprise proposal during photoshoot? There are so many ways to do it and they’re ALL so magical because they all end in the same way- with big, fat YES!

Check out some more beach engagement photoshoot inspiration or get in touch to start planning your surprise proposal!!

This proposal has been featured on Wandering Weddings! To check out the feature and for more surprise proposal inspiration, click here!

This proposal has also been featured on How They Asked by The Knot! To see the full-length feature, click here!


Get In Touch


Follow Me

Small photos of various couples representing the instagram feed of a Washington elopement photographer


Ready to jump straight to my inbox? Whether you're interested in more information, have a couple of questions, or are ready to book with me, getting in touch is the first step!

about me

planning resources

contact me

pricing and info