Fenway Hotel Engagement Session | Jordan + Olivia

Alright, grab yourself a cozy seat, because I’ve got a story to tell you about Jordan and Olivia’s epic engagement session at the Fenway Hotel. Picture this: a beautiful couple, dressed to the nines, at a stunning historic photo location!! A photographer’s dream right?

Fenway Hotel

Oh, let me tell you about the Fenway Hotel in Florida – it’s a real gem! I love photographing at this location and it has quickly become a go-to for engagement sessions. This place has got personality for days. It is located in the heart of Dunedin! This hotel is filled with sooo much charm and character! As soon as you step through the doors, you’re transported back in time to the days of the Roaring Twenties. The vibe is incredible. The decor is a perfect blend of elegance and comfort. But let’s talk about the views – oh boy, the views! Overlooking the sparkling waters of St. Joseph Sound, it’s hard to even find a better spot to watch the sunset let alone take photos!!

The Engagement Session

We kicked off the day by capturing some stunning shots outside of Fenway Hotel. Jordan looked awesome in his classic tux complimenting Olivia in a classy short white long-sleeve dress! If you’re trying to figure out what to wear to your engagement session, let Olivia and Jordan be your inspiration!

When it comes to engagement photos, I always encourage my couples to dress in neutrals. Neutrals like whites, blacks, grays, and earth tones create a clean, timeless look that won’t be distracting! By keeping the wardrobe simple and neutral, the focus remains on you, your partner, and your connection, rather than on bold or busy patterns and colors. This allows for a more classic and romantic feel to the photos!!

Towards the middle of the session, we moved the party indoors. I got to capture some fun shots of Jordan and Olivia sipping on their favorite drinks and sharing laughter and sweet moments. The cozy ambiance of the hotel created the most PERFECT setting for these romantic photos.

But just when you thought things couldn’t get any better, Jordan and Olivia decided to switch things up with a second outfit change. This time, they opted for a more casual look with jeans and casual tops! After, they headed to a nearby park/field for some fun photos. Their formal and casual outfits perfectly captured the different parts of their relationship – the vibe went from elegant and sophisticated to down-to-earth and carefree! I remember being so excited about their outfits and knowing how well they were going to photograph.

Finding the perfect photographer

In my recent blog about What to do when you get engaged, I briefly talked about the importance of finding a photographer you love but, I want to dive a little deeper into that. It is absolutely crucial to find a photographer that you are head over heels in love. We’re talking about capturing some of the most precious moments of your life here, so you want someone who gets your vibe, your style, and your personality. Trust me, when you find that perfect photographer who just “gets” you, the magic they can create with their lens is nothing short of breathtaking.

Think about it – your engagement and wedding photos are going to be plastered all over social media, shared with your friends and family, and cherished for a lifetime. Do you really want to settle for photos that don’t reflect the true essence of your love story? Heck no! You deserve images that make you truly happy every time you look at them. And the only way to achieve that level of perfection is by teaming up with a photographer who not only captures stunning images but also understands you and your partner

And let’s not forget the importance of feeling comfortable and at ease in front of the camera. When you click with your photographer on a personal level, it’s like having a friend by your side, cheering you on, and helping you relax and be your authentic selves. This comfort and connection will be seen in your photos. So, do yourself a favor and take the time to find a photographer who not only has the technical skills but also the passion, creativity, and personality to bring your love story to life in the most beautiful way possible. 

Trust me, when you find that perfect photographer match, your engagement and wedding photos will be nothing short of amazing! 

When Jordan and Olivia reached out to me, I was so happy. We have the same vibe and I was able to clearly understand their vision and what they wanted. Working with these two was the highlight of my year. As their photographer, I couldn’t help but be swept up in the joy and love that came from Jordan and Olivia. Their chemistry was incredible and their love is seriously undeniable. It was a privilege to capture these precious moments for them. If you’d like to see a glimpse into this special day or if you’re looking for engagement session inspo, keep on scrolling for more!!

I hope you enjoyed reading about Jordan and Olivias Fenway Hotel Engagement Session! If you’d like to see more, click here. If you’re looking for someone to capture your special day, click here!


“Our experience will Jill was more than we could have ever asked for! We did both our engagement session and wedding with her and both experiences far exceeded our expectations. She is kind and professional and her work is outstanding. Every time I look at our wedding photos I get emotional because they captured our day so well. If you are looking for a wedding photographer, look no further!”

-Mallory K.

Your Love Story, Joyfully Captured With Warmth and Connection

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