Life has a way of weaving stories together in the most unexpected of ways. For Chelsea and Brandon, their journey is a story of love, faith, and a bit of kismet. Their chance encounter brought them together and with luck on their side, it brought them their dream destination wedding at Round Hill, Jamaica.

Thanks, in part, to winning a once-in-a-lifetime wedding giveaway hosted by Round Hill Hotel and Villas, Taryn Stark Wyant, and an incredible team of vendors, Chelsea and Brandon exchanged vows in Jamaica. This celebration brought their love story full circle, rooted in faith, family, and the joy of doing life together.

The Ultimate Meet-Cute

When Chelsea made the decision to move to Virginia, she was simply searching for a fresh start, a new chapter filled with hope and possibility. What she didn’t expect was that, just one week later, she’d meet Brandon, the man who would forever change her story.

“I first noticed his smile,” Chelsea recalls, “but it was our very first deep conversation that sealed it for me. Even before our first date, I knew he was the one.”

That first date took place at Mike’s American Grill, a now-sacred spot in their relationship. Though they came from different worlds, their spirits aligned through laughter, challenges, and a shared commitment to love and faith.

A Proposal to Remember

If Chelsea had a favorite holiday, Thanksgiving would win every time, and Brandon would take that knowledge and bring her the surprise of her life.

Thanksgiving day 2023, Chelsea felt something was off. “Brandon seemed distant, and my family was acting strangely,” she admits. What she didn’t know was that everyone was in on a carefully planned surprise.

“Surrounded by our loved ones, Brandon proposed, making my favorite holiday even more meaningful,” recalls Chelsea. “The joy, the love, and the overwhelming gratitude in that moment are something I’ll cherish forever. Funny enough, I was so overwhelmed that I don’t even remember him asking so I had him re-propose later!”

An Extra Twist of Luck and Fate

As wedding planning began, Chelsea and Brandon entered a giveaway that Round Hill Hotel and Villas, in partnership with Taryn Stark Wyant, was hosting — and WON! The giveaway included the ceremony venue at the iconic Round Hill Hotel and Villas, expert planning by Taryn Stark Wyant, storyboard wedding design by Sabbag Design Studio, photography by Dave Robbins Photography, cinematography and social media teaser by Harmland Weddings, floral design by Stoneblossom Florals and luxury travel planning by Britta Heath Travel.

Destiny delivered for Chelsea and Brandon because they both envisioned a place that felt timeless, elegant, and filled with natural beauty. Plus, Brandon’s mom is from Jamaica, so a destination wedding at Round Hill Jamaica in Montego Bay, Jamaica, fit the bill perfectly.

Known for its sweeping ocean views, lush tropical gardens, and historic Ralph Lauren–designed villas, Round Hill embodies both romance and sophistication. It became the perfect backdrop for the most important day of their lives.

Guests were treated to more than just a wedding, they experienced an immersive celebration. From lounging by turquoise waters to indulging in gourmet island cuisine, every detail blended relaxation with festivity. For Chelsea and Brandon, it was important that their loved ones not only witness their union but also share in a once-in-a-lifetime experience.

A Celebration of Faith and Family

At the heart of Chelsea and Brandon’s wedding day is their faith. “Above all, we want to honor God as we enter this new chapter together,” Chelsea shares. Their ceremony was filled with meaningful touches that reflected their devotion, surrounded by family who have supported and loved them every step of the way.

Their vows were held on the property’s Infinity Pool Sun Deck with guest’s chairs facing the aisle. The bride walked down the stone path with live violin played by Gabrielle Clark and the aisle flanked with garden roses in hues of coral, pink and red. The abundant and vibrant floral design by Stoneblossom Florals created the most intimate and stunning backdrop, fusing the relaxed luxury vibe of the resort to the tropical destination it is in.

Radiant smiles surrounded by their closest loved ones marked the moment they said “I do” to forever in paradise, set in a dreamy wedding design.

Dinner Under the Stars

The couple and their 46 guests celebrated al fresco style on the property’s Seaside Terrace. With tables topped with green linens by Blooms and Branches and floral runners by Stoneblossom of red anthurium, pink orchids, garden roses and chenille, white tapered candles in hurricane lanterns, and King Louis cane-backed dining chairs, the setting was truly a dream.

Hanging lanterns and table-top candlelight illuminated the ethereal space as the group danced to the music of 876 Sounds and dined on an exquisite dinner under a canopy of stars.

A Final Love Letter

The couple couldn’t have been more enchanted and overwhelmed with the beauty of their wedding day and they let their planner, Taryn Stark Wyant, know. Shared on social media, Chelsea wrote to Taryn, “You didn’t just plan a wedding — you chose me. You saw the vision before it was fully formed and called it into being with love, elegance and excellence.” The bride goes on to say, “Every detail was perfectly executed…you quite literally gave us the wedding of our dreams. More than a planner, you’ve become family.”

Their destination wedding at Round Hill, Jamaica is proof that love often arrives when least expected, in ways more beautiful than imagined. From a chance meeting in Virginia to a life-changing Thanksgiving proposal, and now to a destination wedding in paradise, Chelsea and Brandon’s journey is a testament to faith, family, and the kind of love that feels destined.

Vendors: Planning: Taryn Stark Wyant; Venue: Round Hill Hotel & Villas; Photography: Dave Robbins Photography; Florals: Stoneblossom Florals; Travel: Britta Heath Travel; Videography: Harmland Weddings; Storyboard: Sabbag Design Studio; Live music: Gabrielle Clark; DJ/Production: 876 Sounds; Stationery: Ledgewood Fine Stationery; Rentals/Linen: Blooms and Branches; Beauty: Enhance U; Bride: @enerche_esthetics; Groom: @sicen_tyson