What Sherriann Keaton, President of Live2Travel, Learned from a Lifetime of Travel

For many travel advisors, Sandals Resorts is one of the premier suppliers for clients looking for Caribbean all-inclusive travel. For Sherriann Keaton, it represents something far more personal. The all-inclusive company didn’t just launch her career — it changed the course of her life

Sherriann Keaton is the president of Live2Travel, a luxury travel agency and part of the Envoyage network. With more than 30 years in the travel industry, Keaton built her agency around the principles she’s embraced throughout her career: treating clients with care and taking a personal interest in delivering unforgettable memories.

“Sandals really shaped my life. It’s the blueprint of my life,” Keaton told Travel Market Report. “I think because of Sandals is who I am today.”

“Sandals really shaped my life”

Keaton was born and raised in a small rural farming community in Jamaica. Describing her upbringing as humble but happy, she paints a picture of a close-knit family, spending much of their time outdoors, participating in activities like cricket.

When Keaton was older, an aunt gifted the family a black-and-white television. This was Keaton’s first real glimpse of life outside of her small community, and introduced her to the world of hospitality.

“I would usually see the hotels on TV, and I was like, ‘I got to get there. I have to get there.'”

Before long, she did get there. While completing a work experience placement after graduating high school, Keaton was encouraged to apply to Sandals Montego Bay. She was paired with Novlette Symister, who would become her mentor. After her Sandals interview, Keaton was told she wasn’t a good fit, but the manager took a chance on her regardless.

“I was young, I was full of life. I was ready to take on the world,” said Keaton.

Leaving the familiarity of her small community to dive headfirst into a position at the resort was a trial by fire for Keaton. The Sandals was located four hours away from her home, and she was hired to be an entertainment coordinator — then called a playmaker. The role involved singing and dancing in front of guests.

Keaton told TMR that she felt overwhelmed the first day she stepped onto the resort for her new position.

“When I walked in and saw that lobby and the layout, and I saw the …resort ocean, and the waiters in their uniform and the front desk staff in their uniform, my mouth fell on the ground. I swear, I thought I walked into paradise,” she said.

Keaton stayed at Sandals for approximately 10 years, working her way up from playmaker to front office receptionist, then front office supervisor, and then finally front-of-house manager. During that time, she proved her capabilities to the company and took on more and more responsibility, even training the front of house staff for new resorts like Beaches Turks and Caicos, which opened in 1997.

Keaton’s hard work and competency paid off. She won a Sandals scholarship to study hospitality at Hocking Technical College in Ohio, traveling back and forth between Jamaica and the U.S. while continuing to work. This was her first time visiting the country, and the experience broadened both her education and worldview.

Later when Keaton was pregnant with her son, she made the decision to move to the U.S. permanently in search of better opportunities to support her growing family. This was no light decision, however: not only did she need financial help, but once she was there, she faced studying post-secondary studies with a newborn.

“I decided to apply for Florida Metropolitan University in Fort Lauderdale. At that time… being an international student… you had to prove that you had $20,000 US in an account and I had $2.00 in an account,” Keaton recalled. “I had help from family members… I migrated and I got enrolled in school and I had my son in Florida, and that’s how that world started.”

“I didn’t realize I applied [to be] a travel agent”

After finishing school, Keaton moved from Fort Lauderale to New York City in pursuit of a hospitalitiy career. She told TMR that she faced an uphill battle, and that the experience was more challenging than she had originally anticipated.

“I decided to move to New York, because I wanted bigger and brighter things. I’d never been to New York… I was so engulfed in fashion… I was watching Sex and the City. I was like, ‘I gotta get there,'” she said. “While I was in New York, I realized, well, it’s not as easy as I think it is on TV.”

Eventually, Keaton applied to a job with Liberty Travel — a name she was familiar with from her time working at Sandals. At the time, she believed she was applying for a customer service job. It wasn’t until later that she realized she would be working as a travel agent.

“I swear to you, I didn’t realize I was applying for a travel agent,” she said.

Shortly after applying, she got a call to schedule an interview. Next thing she knew, she had been thrown head-first into the world of travel planning.

“I was overjoyed and I started working in travel. I didn’t know anything about selling. I didn’t know anything about any destination. I had no idea where these places were, how I was going to do it. It was just so overwhelming,” Keaton said.

Although the new position was daunting, Keaton was not one to back down from a challenge. As she had back when she started at Sandals, she put her head down and dedicated herself to learning as much as she could in order to exceed in the new role. That hardwork paid off.

“I have always tried to be 10 steps ahead of anything that I’m doing. I’m going to research, I’m going to call, I’m going to read, I’m going to look it up. It doesn’t matter how simple the task is,” explained Keaton. “So when I got the job, I was researching, reading, calling, trying to navigate my way. And Liberty Travel provided so much training for me over the years.”

As she grew more comfortable in the role, Keaton grew to love being a travel advisor. She told TMR that she got immense satisfacction from helping her clients realize their travel dreams. To this day, even as the president of a successful travel agency, she still values the relationships she has with her clients.

“That’s how I fell in love with travel. It was more of the feeling of giving the clients that experience … Yes, it was nice closing the sale, but it was more of the experience for the customer and when they come back, the joy… that’s how I fell in love with it. It’s the feedback from the customer.”

Keaton reamained employed by Liberty Travel until the COVID pandemic shut down the industry. The company gave her the option to launch her own business under the Independent by Liberty Travel banner (which later became Envoyage), and she recruited several strong agents who were going to be furloughed by Liberty.

“That’s how it took off… Now we have 20 (advisors) … They believed in me. I believed in them and they trust me… They took a chance on me as I took a chance on them.”

“Travel advisors are therapists”

Just looking at the numbers, Live2Travel is a successful business. In fact, she won Top U.S. Agency at Envoyage three years in a row. For Keaton, however, sucess is less about sales earnings and more about forming human connections.

“Clients love their travel advisors because they feel that they can trust us. We’re therapists. … We’re always going to give them what they need,” she explained.

Keaton’s customer service philosophy can be broken down into three parts: consistent customer service, prioritizing relationships over sales, and continuous learning. She told TMR that she treats all her cleints the same, regardless of their travel budget, and makes a point to maintain the relationship before, during, and after travel. The key ingredient, however, is keeping up with all the training available, which ensures that the clients are benefiting from up-to-date knowledge.

Looking back on the over 30 years that she’s worked in the industry, Keaton is optimistic about the future — for her own agency and for newcomers to the industry. Her advice: never forget the human element of travel planning, and continuous learning.

“Keep your head up. Communicate with your clients. Stay focused on what’s important. Research, live in the moment, adjust and live in the reality of travel,” she said. “The benefits are great. The outcome is great. You have to do it from a place of passion. You have to do it from a place from your heart… the clients do feel it.”