Taylor & Drew
Taylor & Drew

Taylor and Drew say I Do!

Taylor Case
and
Drew Caulfield

#TaylorAndDrewSayIDo
on
April 19th
2026
in
Montego Bay
Jamaica
482 Days
20 Hours
39 Minutes

The Story of Taylor and Drew

Taylor and Drew’s love story began in June 2020, when the world was facing uncertainty and challenges. Amid the pandemic and the personal struggles that came with it, they fell in love. Drew became Taylor’s unwavering support, standing by her through the ups and downs, offering love and strength when it was needed most. Together, they navigated the hurdles of mental health, growth, and life’s unpredictable twists, building a bond that only grew stronger with time.

In the summer of 2022, they took a bold step forward together, packing up their lives and moving to Des Moines. It was a fresh start, a new chapter that brought them closer as a couple and allowed their love to flourish in ways they never imagined. Over the next two years, their relationship continued to deepen, with each day bringing new memories and a stronger commitment to one another.

Then, on April 20, 2024, while vacationing in the vibrant city of New Orleans, Drew took Taylor on a private carriage tour of the historic French Quarter. The romance of the city and the magic of the moment set the stage for a life-changing question. In the heart of Jackson Square, surrounded by the cheers of strangers who felt like family, Drew asked Taylor to spend forever with him. And with all her heart, Taylor said yes.

Now, as they prepare to celebrate their love with family and friends, Taylor and Drew are excited to share this next chapter with the people who have supported them along the way. Their journey has been one of love, growth, and resilience—and they can’t wait to see where it takes them next.

Our Destination

Sandals Montego Bay

Spanning the best private, white-sand beach in Jamaica, this playful and romantic resort is where the world first fell in love with Sandals. The calm, reef-protected beach is perfect for every type of water sport and guests can indulge in unlimited dining at nine gourmet restaurants serving authentic regional cuisine. Experience the casual island vibe from the comfort of your private seaside suite where our Butler Elite await to fulfill your every whim. Everything is just steps from water's edge and, best of all, it's all included.