TORONTO — When Rachael Shilling looks back at her career, the shift into destination weddings feels less like a pivot and more like a natural evolution.

A Destination Wedding Specialist with Liz Moore Destination Weddings in Victoria, British Columbia, Shilling has been a travel advisor since 2015. Before specializing, she focused on all-inclusive resort travel and group vacations throughout Mexico and the Caribbean. That foundation, she says, made the move into weddings seamless.

“I’ve always had a strong love for all-inclusive destinations, and being able to align that passion with helping couples plan one of the most important days of their lives created a true aha moment for me,” she says. “It genuinely felt like this was what I was meant to be doing.”

Today, Shilling is a top-producing advisor within her agency, a Top 100 Travel Advisor in North America for Hyatt Inclusive Collection, and regularly manages multiple wedding groups ranging from 20 to more than 100 guests. For advisors considering a niche, her journey offers a clear roadmap.

LEARNING FROM THE BEST

Shilling did not enter the wedding market from scratch. Years of booking Caribbean resorts and coordinating group logistics gave her a strong operational backbone.

“Transitioning into destination weddings felt like a natural progression,” she says. “I already understood resort products, group logistics and supplier processes so many of the core skills simply transferred over.”

The main learning curve, she notes, involved wedding-specific contracts, packages and navigating resort wedding departments. “But with proper training and mentorship, that piece came together quickly.” 

Shilling credits much of her early acceleration to intentional learning during her first year at Liz Moore Destination Weddings.

“I made a very conscious effort to listen and learn from the best,” she says. “I reached out to top-producing agents within the company, as well as Liz Moore herself, and asked direct questions like: What are you doing differently? What does your quoting process look like? What resources and supplier relationships do you rely on most?”

She studied workflows, quote structures and communication styles, then implemented those best practices into her own business.

“Learning from experienced, high-performing advisors gave me a strong foundation and significantly shortened my learning curve,” she says.

In addition to internal mentorship, she immersed herself in supplier webinars, internal trainings, site inspections and conversations with business development managers and wedding teams. She built detailed notes and developed curated lists of go-to resorts based on wedding style, budget and guest demographics.

More recently, refining internal systems has been a game changer.

“Organized tracking and email workflows have made a huge difference,” she says. “These efficiencies allow me to work faster, stay organized and provide a more polished experience for my couples.”

BUILDING CREDIBILITY

Although she was new to the wedding niche, Shilling was not new to travel. That distinction helped her build early credibility.

“I’ve been a travel advisor since 2015 and had already visited numerous all-inclusive resorts before specializing in destination weddings,” she says.

She leaned on personal resort knowledge and paired it with insights from experienced colleagues to guide couples toward properties known for strong wedding programs.

“Because many of my personal favorite resorts already aligned with top-performing wedding resorts, it made presenting and selling these properties feel natural and authentic,” she says.

Support from resort wedding teams also played a key role in ensuring smooth early bookings, which in turn built trust and referrals.

THE POWER OF REFERRALS

Shilling’s first destination wedding clients came largely through her agency, which generates significant lead volume. Over time, however, referrals became her strongest growth engine.

“Today, my strongest source of new business is referrals from past couples, wedding guests and word-of-mouth,” she says.

Online reviews and social media also contribute, including inquiries through her Instagram account. Ultimately, she believes exceptional service fuels sustainable growth.

“Providing a great experience naturally fuels continued referrals, which has been key to my growth.”

All this underscores the importance of relationships, particularly with clients, resorts and wedding coordinators. 

“Strong relationships lead to faster responses, better problem-solving and sometimes added value for couples,” she says.

For new advisors, her advice is simple: introduce yourself, attend trainings, follow up and always be professional and reliable.

AVOIDING COMMON MISTAKES

When asked about common mistakes many new advisors make when entering the destination wedding niche, Shilling points to three main ones: underestimating timelines, overpromising and failing to set clear expectations.

“New advisors sometimes feel pressure to always have an answer, but honesty is far more valuable,” she says.

Noting how wedding packages and policies change frequently, Shilling advocates for transparency over guesswork.  

“Clear timelines, regular updates and following through on what you say you’ll do builds trust,” she says. “Even a quick check-in to say you’re still waiting on information reassures couples that they’re a priority.”

Destination wedding clients also face unique challenges, Shilling adds, from budget management and guest logistics to resort availability. She addresses these with proactive communication and backup options.

“I overcome these challenges by setting realistic expectations early, providing clear comparisons between options, and guiding couples through timelines step-by-step,” she says. “Proactive communication and having multiple backup options help keep planning smooth and stress levels low.”

PROFITABILITY AND PASSION

Shilling is unequivocal about destination weddings’ earning potential for travel advisors, saying the niche is both incredibly rewarding and financially strong.

With personal experience visiting nearly 70 all-inclusive resorts, she saw an opportunity to leverage that knowledge into a group-based model.

“Transitioning from selling trips for a family of four to managing wedding groups of 80–100 guests significantly increases earning potential, while still allowing me to focus on destinations and products I know inside and out.”

And yes, there are perks.

“You can’t ignore the travel perks that come with booking groups, that part is pretty great too!”

THE SECRET SAUCE

Ask Shilling what truly sets her apart and her answer is clear: confidence, honesty and care.

“I know what I’m talking about, and when I don’t, I’m transparent and resourceful enough to find the right answer,” she says.

She prides herself on being responsive, organized and deeply invested in each couple’s experience.

“Most couples come into that first call feeling overwhelmed, and my goal is to take that stress away by saying, ‘I’ve got you, I’ll handle this.’ That sense of relief is everything.”

Her final piece of advice to advisors considering a niche?

Own your value.

“I’m never bothered if couples speak with other agents because I know my worth and the value I bring,” she says. “Couples can feel that, and that’s ultimately why they choose to book with me.”