Former Crew Aubrey Chesson’s Cup of Sugar Concierge Helps Neighbors

14 December 2022 By Aileen Mack
Aubrey Chesson
Aubrey Chesson

Associate Editor Aileen Mack joined Dockwalk in July 2018. She is a graduate of the University of Florida with a bachelor’s degree in journalism. If she’s not at a concert or coffee shop, she is lost in a book, movie or a YouTube rabbit hole. Email Aileen at

After four years in the yachting industry, Aubrey Chesson began her transition ashore at the end of 2019. When COVID shut everything down, including the first wedding she was going to oversee with former crewmember Abby Gallagher of Blue Orchid Events & Design, she needed another plan. This began what would become her concierge service, Cup of Sugar.

“The beginning idea was that I have acquired all these random skills that allow me to do lots of tasks to help people,” she says. “Yachting really honed the eye for detail, and that people need someone to call and rely on to help them.” As a crewmember, she was a bit of an all-arounder, holding positions as a stewardess, deck/stew, deckhand, mate, sous chef for two months, and volunteer engineer when help was needed.

Due to the pandemic, Chesson had to get creative to get clients. She printed business cards, went out at 4 a.m., and hung them on mailboxes advertising that she would go grocery shopping for people so they didn’t have to risk exposure. This ended up being hugely successful as she spent the pandemic grocery shopping, running errands, and chauffeuring the elderly to their doctors’ appointments. She started as a “household helper,” doing whatever someone needed to feel their to-do list was being met.

“My business took off and defined itself when I was trusted to pack and move four estates for a client when their parents passed away,” Chesson says. Through word of mouth, she has become one of the people to call when those coming to South Florida need to get tasks accomplished. Cup of Sugar provides services in Wellington, West Palm Beach, to Fort Lauderdale, but will travel anywhere (flights, accommodation, and a vehicle required).

The team organizes closets and homes, house sits, does personal shopping, and offers completely hands-off moving services. “The beauty of my business is that we work independently. Clients do not micromanage us,” she says. “So when we move homes, it’s a really fun evolving process of how to make it the most efficient and improved each time. Now I am just known to be able to do just about anything my clients need.”

With the business growing, she is expanding her service offerings and coming back into yachting as an onshore assistant. She has one full-time employee, and when she needs more help, she hires contractors, mostly from the yachting industry. By teaming up with local businesses and trades people who have “yacht-level” execution and passion for what they do, she can offer clients top-notch service and support the community.

“I will provision, buy party supplies, handle shipping and receiving if they have to leave port early and cannot receive the packages, act as a client advisor and find day charter vessels, set up interiors of new boats and implement organization systems, stand in as day-of crew for turnovers if extra hands are needed … ,” she says. “The little things add up. We all wish we had like five more arms to accomplish more at once. I take the little things off your plate.”

Cup of Sugar also provides services that focus on the energy of a space, such as home cleansings with sage and sealing and protecting them with reiki and sourcing and purchasing crystals to accomplish certain energies (more clarity, protection, energy, etc.).

Her plans for Cup of Sugar in the future involve creating organizations and businesses to help uplift the community and introduce her clients to other people in the community doing amazing things. This includes monthly meetups “for young entrepreneurs, women, men, spiritual ceremonies, and general community where everyone has an outlet to be seen, heard, and loved.” She also hopes to create a center for children to attend after school and in the summer with activities that help them discover their natural talents.

“I will bring in teachers of each field that will host these mini classes for the kids to play and create and figure out who they are,” she says.  “Along with that, I want to teach them all mediation and emotional regulation, how to have healthy relationships, self-defense, and basic financial habits (budgets, investing, credit cards, etc.).” Taking from her experience, Chesson wants to teach the children all the things that are needed in adulthood but not taught in school.

“I lead with my heart and truly love what I do,” she says. “My business is an extension of me — helping people is my purpose. I just found a way to turn it into a super easy and flowing business model.”


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