When you’ve worked in the wedding industry for years, getting engaged and planning a wedding yourself can feel pretty high-stakes. Expectations are inevitably higher, yet the celebration needs to stay on budget and be accessible for guests. If this is the place you find yourself in, let the destination wedding planning journey of Tina Wong, founder and lead designer of Grace and Ivory, inspire you to not only rise to the occasion but to shoot for “practical yet authentic.”

Our story starts in a local Chicago haunt known for its upscale cocktail bar vibes, low-light, good food and raw oyster specials called The Press Room. After striking up a conversation on a dating app, Tina and Matt met there for drinks. As Tina tells it, Matt had an air about him from the jump that simply melted her.

“I realized immediately that I loved talking to him,” Tina remarks, “ … his wit and the sound of his voice.” Can it get any cuter? “We closed down the Press Room talking over drinks till 10 p.m., and it was a good sign that he also was having a good time.”

The night didn’t end at 10 p.m. In a move that signaled just how well the conversation was flowing, Matt suggested they move the party to a nearby bar that stayed open until midnight. From that first night in the West Loop, the momentum never stalled. Soon the Chicago-based couple found themselves planning a life together and a wedding that would take them far from the Windy City.

The Couple Chose a Destination Wedding in Playa del Carmen for a Relaxing Guest Experience

While Tina and Matt call Chicago home, they knew they wanted their wedding to feel like a true escape. For Tina, who has lived abroad in Asia, the pull of a far-flung locale was strong, but her “practical yet authentic” mantra won out.

“We were enticed by the idea of a celebration weekend,” Tina says. “If it was in Chicago, it would be harder for everyone to shake off the work week. We loved the idea of a beautiful, tropical destination where we could truly relax.”

They looked at Europe and Asia, but ultimately Mexico hit the sweet spot of budget, ease of travel for their guests and personal sentiment. Having traveled to Tulum and Holbox Island the year prior and getting engaged on Grenada Island, the Caribbean coast felt like a natural extension of their love story. They landed on The Fives Beach Hotel in Playa del Carmen specifically because it avoided that “sterile” resort feel. With its nods to local Mayan culture and lush, nature-connected grounds, it provided the perfect backdrop for a guest list that eventually grew to 113 of their closest friends and family.

A Designer’s Wardrobe: Tina Wong Wore Five Custom Grace and Ivory Gowns and a Family Heirloom

As the founder of Grace and Ivory, Tina knew the question on everyone’s mind: What will the designer wear? Rather than settling on one look, Tina used the weekend as a creative canvas. She designed or curated five distinct looks that transitioned from vintage-inspired lace to high-octane party wear.

The wardrobe journey began at the rehearsal dinner, where Tina wore a short, vintage-inspired lace dress with off-the-shoulder long sleeves. “I love Chantilly eyelash lace,” Tina notes, “so it was wonderful having this touch in one of my first wedding looks.” For the welcome party, she shifted gears into a custom-beaded fabric featuring a flowy skirt that was perfect for the ocean breeze.

On the wedding day itself, Tina’s ceremony gown was a masterclass in modern tradition. While she initially considered an A-line silhouette, she followed her heart to a floral-inspired lace fit-and-flare. To complement the tropical destination, she opted for nude and pink blush accents rather than a stark ivory, matching a palette of mauve, neutrals, greens and pops of dark plum.

But perhaps the most sentimental look of the weekend was Tina’s reception change. She stepped out in her mother’s traditional Chinese Qi Pao, which was a dress made in Hong Kong decades ago for her mother’s own wedding festivities. It was a stunning tribute to her heritage that brought a deep sense of family history to the Mexican coast. Finally, to close out the night, Tina changed into the Hailee dress. This was an empire-waist beaded silk mini from the current Grace and Ivory collection, and it was designed specifically for dancing.

Working with Wedicity Helped Navigate Destination Wedding Logistics and Resort Vendor Fees

Planning a wedding of this scale from another country is no small feat. Tina is the first to admit that even for an industry veteran, the “nickel and dimed” nature of resort planning can be a headache. That’s where Tionna Van Gundy of Wedicity came in.

“Hiring Tionna to have a comprehensive approach to planning really helped with everything,” Tina says. “The resort team was helpful, but they aren’t involved in the key parts of the planning like the welcome bags, rehearsal dinner and the overall design details.”

Because they didn’t do a pre-wedding site visit, Tionna became their boots on the ground and their logistics mastermind. Together they navigated the outside vendor fees of the resort to ensure Tina could bring in the specific talent she wanted, such as the team at Amore Creative for stationery.

Personalized Details Included Custom Stationery and Creative Dog-Themed Cocktail Stirrers

The authentic part of Tina’s vision shone through in the small, thoughtful touches that filled the weekend. Understanding the humidity of Playa del Carmen, they provided bamboo fans with silk bows at the ceremony. “I didn’t like the look of program fans,” Tina explains, “so the bamboo felt a little more elevated.”

At the tables, guest names were laser-cut into menus designed by Amore Creative. This was a detail Tionna hand-carried from Chicago to Mexico to ensure they arrived safely. Even the cocktails had a personal touch. The couple used custom drink stirrers featuring the heads of their two 70-pound dogs who couldn’t make the trip. “We already had a funny photo of our lab/hound dog wearing a sombrero,” Tina says, “so we got that one printed specifically for the Mexican setting.”

The guest experience was further elevated by custom reusable canvas welcome bags. Instead of the typical paper bags that get tossed, these were used by guests all week as beach and pool bags. Inside, guests found survival essentials like Liquid IV and Advil along with local Mexican candy the couple had personally scouted and purchased.

The Couple Exchanged Personalized Vows in a Meaningful Ceremony Led by a Family Member

The wedding day culminated in a ceremony that was as personal as it was picturesque. Tina’s cousin Brian officiated, bringing a level of intimacy that only a family member can. Having seen their relationship blossom from the very beginning, Brian spent months interviewing Matt and Tina separately to weave their specific quirks and triumphs into the service.

Under the tropical sun, surrounded by the sound of the ocean and the people they love most, Tina and Matt said their own vows. It was the perfect culmination of a journey that began with oysters and wit in a Chicago basement bar.

Pro Planning Tips: Advice for Couples Planning a Successful Destination Wedding

Reflecting on the experience, Tina has a few nuggets of wisdom for those following in her footsteps. “Try not to procrastinate,” she warns. “Even with my background, some tasks took longer than expected, especially the design elements.”

She also stresses the importance of choosing a venue that aligns with your vendor needs. “Before you pick your venue, you need to decide what you’re okay with. Some resorts require you to use all their vendors. I chose The Fives because they allowed me to bring in outside vendors for the elements that mattered most to me.”

For Tina and Matt, the practical yet authentic approach didn’t just result in a beautiful wedding. It resulted in a weekend where 113 people felt like family, where heritage was honored and where a designer got to see her own love story reflected in every lace stitch and silk bow.