NAVY PIER DOWNTOWN CHICAGO VINTAGE SAILBOAT ENGAGEMENT SESSION: MELISSA MARIE PHOTOGRAPHY

Smooth Sailing (Sort Of): A Nautical Chicago Engagement Session

They were just kids when they first got together, so it felt only right that their engagement session matched the playful spirit of their love story. (Sure, every session is fun, but let’s be honest—the setting sets the tone.) Sophisticated rooftop dinner vibes? Cute, but not for these two. Instead, they rented a vintage sailboat to cruise the Chicago skyline at sunset—and ended the night with ice cream cones at Navy Pier. So fun!

Now, let me tell you something about being on a sailboat (let alone taking pictures) on Lake Michigan: it looks effortless, but it takes a lot of intentionality. Just like their relationship. When you’ve been together since childhood, it’s not always smooth sailing—literally or figuratively. And if you know anything about the Great Lakes, you know Lake Michigan can throw some serious waves at you. This wasn’t just a cute ride in calm waters—it was balance, teamwork, laughter, and yes, a bit of hanging on for dear life. They made it look easy!

Bonus points to them for the brilliant idea to save their ice cream cones till the very end. July 3rd in Chicago? You better believe those things were melting faster than it'd take me to photoshop out the stains.” And with white outfits on a wobbly boat? Yeah, smart move.

Speaking of July, here’s a little photographer pro-tip: Schedule your engagement session on a weekday if you can. Fewer crowds, fewer curious onlookers yelling “Awwww!” at you, and in a city like Chicago, way less traffic. That said… maybe avoid holidays. July 3rd was technically a Thursday win—but also the eve of one of the busiest weekends in the city. I left my place at 3PM for a 6PM shoot. Normally a 40-minute drive. It took nearly 3 hours.

What saved me? Booking my parking space ahead of time. I used a parking app, snagged a sweet deal, and ended up parked steps from the dock. Every garage in the area was full. Trust me—plan ahead, especially for city shoots.

So would I do it again? A thousand times yes. If you’re renting a vintage sailboat, I’ll follow you around the whole calendar! (:

Here’s to lifelong love, big waves, and the sweetest endings (with sprinkles on top).