Ohhhhh you guys… this engagement session is everything. It’s sentimental, romantic, whimsical, playful and one to talk about for sure. It’s so important to make your engagement session a true reflection of you two and your story. David and Olivia chose a to have their session on a sailboat for this reason. There are a few different ways for you to do to make your engagement session stand out from the rest while also being authentic to you. Understanding the best attire, location(s), introducing your wedding style, and elevating aspects of your favorite date will help you achieve this. And what better way to understand this than celebrating David and Olivia’s engagement session.

Golden Hour Proposal on a Sailboat

David and Olivia met their freshman year at Taylor University and have been together since. Both of them, having grown up near Lake Michigan, have a deep appreciation for the water. When it came time for David to propose, he booked a sailing charter during golden hour in May and as the sun dipped below the horizon, he knelt on one knee and popped the question. Can you even imagine? SO DREAMY!

And dreamy doesn’t begin to describe these two. They really are young and in love. You watch them with each other and they are sweet, playful, gentle and constantly giggling.

Sailing Engagement Inspiration

From the beginning, talking with Liv over the phone, she felt like a fast friend. Her joy and love for life is truly contagious. Olivia also has a love for photography which made planning their engagement so much fun, hearing her vision for the aesthetic of the photos but also the story and emotion she hoped they would carry.

I was very quick to recommend incorporating a sailing charter since it’s such a romantic beautiful part of their love story and childhood, growing up near the water. They decided to start the beginning of the session on the beach for some more classic photos and then end the night with a sailing charter. The best of both worlds if you ask me.

Incorporating an activity in your session that’s very natural in your dating life is truly a must. And it can be anything! For David and Olivia it was sailing but I’ve had couples mix cocktails, play games, have a picnic, go for a hike, get coffee, and the list goes on. This was my first sailing engagement and I really hope not the last.

Picking Your Engagement Session Outfits

David and Olivia decided on one formal outfit and one more casual outfit, which I highly recommend. It allows for two different types of poses; some with more movement and playfulness and others that naturally lend themselves to be more traditional/classic and romantic. Also, these are a little ode to your wedding day so they should have a more elevated look than every day.

Olivia wore this beautiful whimsical white dress and even though we started with that outfit at the beach location, I had her wait to change so we could get her flowing dress on the sailboat as well. FAVORITE SET OF THE WHOLE NIGHT! Her dress caught the wind and was an unpaid actor for sure. I always love when brides choose a white sun dress for their engagement session. It really feels bridal without being too formal and set this season apart from the several portraits they will have together in the years to come.

Because most of the poses for the sailboat naturally lent themselves to cuddling, sitting or more editorial style shots, we did poses with lots of movement on the beach, as well as traditional photos.

I like to ask my couples if they are using their engagement photos on their save the dates and if so what orientation their save the dates are. Not always, but MOST of the time couples choose a photo where both are looking at the camera and smiling and so I like to provide a few intentional photographs with that in mind in the orientation they hope to use something that photo in. It’s one way that I mentally make sure I’m doing my best to provide for their immediate printing needs. I usually include those photos in 24-hr previews so they can work on their save the dates immediately and those are the pictures parents really love to see too.

Golden Hour on the Sailboat

These two didn’t need much direction at all when it came to posing, it was more affirming things they were already naturally doing. They were so present with each other, so encouraging, and didn’t wait for me to prompt a kiss or cuddle. Everything about their engagement session was so authentic and real to these two.

When we got to the slip, for our sailing charter, we realized that this was the exact same captain and sailboat when they got engaged. I had booked it from what I felt would look best from a photography standpoint and it just so happened to be the same. So serendipitous. As we chartered out to Lake Michigan during peak golden hour, I asked more questions about the two of them, about the proposal and what they were excited about. It set the tone for our time out on the water. It was more intentional, quiet as we listened to the sail whip in the wind and water lap up against the boat. After a few minutes on the boat in their formal outfits, they changed into more every day clothes. As their session came to a close, the sun started to kiss the horizon. We paused and just enjoyed the sunset and our captain chartered us back. The light of the day was gone by this time and I surprised them with a charcuterie board to enjoy up at the bow. And I sat back with the captain on the way back to give them some time to themselves.

Engagement photos are so special already but when you incorporate an activity, like sailing for these two, it’s takes the session to the next level and truly tells more of your love story. And who wouldn’t want that?