Skip to main content

IN THE SPOTLIGHT: Rebecca Cleveland, Third generation in local art

March 8, 2024
By Sheila Evans

The COVID pandemic was a terrible thing, but it had some incredibly good and unexpected impacts in some people’s lives. Rebecca Cleveland is one of those lucky people. It was when she discovered she really was an artist. 

Rebecca is the daughter of a celebrated artist, Gail Cleveland. She is the granddaughter of another acclaimed artist, Wini Smart. She loved art but did not see the spark her mother and grandmother had as artists. But the pandemic opened a door for her to discover that her own talent was not a competition or a shadow of these great ladies, but the result of years of immersive training, inbred skill and natural talent that brought her joy when she let it surface. 

“Growing up around my mom and my grandmother, the talented artists that they are, I was incredibly intimidated.” Rebecca said. “I just thought, ‘That’s great for you; I don’t think I can do that.’ They are strong women, running businesses and taking care of children and painting, and I just thought, ‘I just don’t think that’s the life for me.’ But there was always something that was missing, always.”

When the pandemic hit, Rebecca was running a cafe in New Jersey and doing well. She found she had time on her hands, though, since there was no traffic coming into the cafe. At the same time, Rebecca’s parents, Gail Cleveland and Terry Waite, were dealing with a crisis in Boca Grande. The studio they had owned for decades lost its lease as the building it was in was being sold. They needed to relocate or close.

“My parents and I are incredibly close,” Rebecca said. “We talk every day on the phone, but I was living in New Jersey when everything happened and the building was for sale and they were unsure what they were going to do, and where they were going to go. Something just clicked in me. I wasn’t really painting yet. I had so much time on my hands and my mom suggested to me, ‘Why don’t you just start sketching? Start painting something, maybe that’s what you’re missing in your life.’” 

Rebecca admitted there was something missing, but she did not know what it was. Gail knew.

“I grew up in the art gallery,” Rebecca explained, noting that the original, and still flourishing Smart Studio is in Maine. Gail and Terry still own that gallery, while Rebecca now owns the Smart Studio in Boca Grande. Both galleries were established by Wini, however, so they have always been part of Rebecca’s life. 

“I spent my childhood there,” she said. “At camp I would make these little sea shell creations and sit in the stairwell next to the shop and sell them to the tourists. So yes, we were always creating together. She always encouraged me to actually take lessons, do art; and I did, here and there. I would go on painting excursions with her, but I didn’t have an interest in doing it as a profession.”

Now as an adult, however, and with nothing better to do, when Gail suggested she try focusing on her art, she decided to give it a try. 

“So I went to Michaels and I got some ‘learn how to sketch books,’ not that I hadn’t done it before, but with art you are constantly growing and learning or you’re just going to stay complacent. You want to keep expanding and doing better. I would walk to the flower shop right in the same plaza, and I would get a little bouquet, and I would just start sketching it. Eventually I got water colors and I would send my mom all the pictures.”

Gail continued to encourage her and suggested they work together, with Gail as her teacher. It seemed like a good idea, but Gail was in Florida and Rebecca was in New Jersey. Again, the pandemic gave a solution — remote learning. 

“So, once a week I would have a lesson with her. She could set up and I could watch her virtually. I would paint while she did. It got to a point where it was all I wanted to do.” 

It eventually dawned on Rebecca that there was nothing tying her to New Jersey. Why not move to Florida and be closer to her parents, her teacher? 

Rebecca is the mother of two: Abigail, who is 14, and Miles, who is two and a half. The family packed up their belongings and moved to Englewood. Rebecca went to work in the gallery and was part of the team to find a new location for the gallery. That location did materialize in the Old Theatre Mall at 321 Park Ave. It is smaller than the old gallery, but bright and welcoming and full of the art people love, much of it reflecting the beauty and fun of Boca Grande itself.

“My parents kept talking about me purchasing the gallery and moving forward,” she said, “but at that time we didn’t have a location, so I said, ‘Sure, I’ll do that,’ not thinking that we were going to get a location. It still seemed surreal. I still was thinking it was something I could not do. I could watch my mother do it; I could work for her; but I didn’t think that I could do it on my own.”

At the last minute, before they had to be out of the old location, they did get a spot in the breezeway of the Old Theatre Building Mall. 

“We signed a bill of sale, and I became the new owner of the Smart Studio, Boca Grande,” she said. That was in June, last year.

Her parents left for Maine shortly after the sale, leaving Rebecca to organize the shop and make it into her business. She no longer doubts that she can do it – she is doing it.

With two children to raise and a gallery to run, Rebecca still finds time to paint.  

“I don’t have loads of time, but once the kids are in bed, or I have a day off when they are at school or in day care, that’s what I would do – paint,” she said. During the winter, when her parents are in Florida, they work for her now. She is amused by that. Gail takes over the gallery one day a week, giving Rebecca a day off. 

Terry provided a day off for a while, too, giving the two women a chance to paint together, but Terry is her “framer” and is in great demand. She said when it comes to framing, “People don’t want to talk to me or my mother, they want to talk to Terry.” 

She admires Terry’s talent as a woodworker and how he has supported the galleries, even sacrificing his own career path to be part of the gallery team. He no longer can work the gallery, due to the volume of framing he is doing, which is a good indication of how well Rebecca is handling the job of owner. 

“I have never come into work with a dreadful thought,” Rebecca acknowledged. “This has been the most cheerful spot that I’ve ever been able to spend so much time in. Even over the summer, after I  had everything situated, I came here every day and I kept it open, not really thinking that I’d ever have any customers, because it’s the summertime. But I just enjoyed being in here, and I can paint here too, when it’s not the busy season.”

She plans to stay open this coming summer, as well. 

“It feels very lighthearted in here. I feel that it’s not just because I’m in MY gallery, but because the bookstore, and the needlepoint upstairs, and the people who run this building have been just so kind and welcoming, and it really feels like a tight-knit community. I so appreciate that.”

She went on, “When I tell you this town has been so amazing to me…Randy, from the realtor’s office here, he and his son helped me move the big pieces of furniture here. One of the contractors in town took some time off to help me move the even bigger pieces of furniture. And I had the whole summer to just set up in here, which was lucky, because it was very time consuming, with the down-sizing and figuring out how to display everything. I Facetimed with my mom a few times, but I was otherwise on my own.”

While the gallery is in a smaller space, it still is full of a variety of art. Wini, Gail, Rebecca, Terry and young Abigail all have works there. Abigail has begun making “pebble people,” and putting them in scenes in shadowboxes. She has already declared she does not want to run the gallery in the future, but Rebecca just smiles at that attitude and tells her to keep creating.

She regrets that her grandmother never saw her become a working artist, but she feels that she knows and approves of what she is doing. 

“The good things that have happened, I truly feel my grandmother has helped them happen,” she said. “She passed away in 2017, and I didn’t start painting until after she passed away. I may not have started painting when I was three, like she did, but I’ve watched it since that age. I’ve been immersed in it and I really wouldn’t have it any other way.”

She noted that it was “incredibly emotional” to move the gallery, since it had been established in Boca Grande in 1982. She not only mourns this gallery, but the decline in the arts, generally throughout the country. 

“There is so much importance in maintaining that culture and beauty on the island. I think the Art Center is a huge, impactful spot that needs to continue to grow. There are so many artistic people here that are a part of it. It brings me joy to see that there is a community of people who appreciate what we have here. Not everybody gets to have this sort of thing.”

Recently, Rebecca received a call from a stranger, calling late on a Saturday from Boca Grande. She could see that Rebecca had items inside the doorway and was concerned about it. 

“She didn’t need to do that,” Rebecca said, “But that’s how the people in Boca Grande are. I have hundreds of dollars worth of things in that doorway, and not one single things was gone. I love how it’s like a different world here. It’s like an intangible bubble that people want to be part of and can’t always have it. The close-knit community is wonderful. I also love how there’s always something going on. It almost feels like a movie sometimes. There’s always some event and the town’s always alive and people are kind to one another.” 

She had one more thing to add: “Aside from that, I love the beach, the sunsets. I feel anywhere I could turn there would be a spot for me to paint. Among my favorite things to paint around the island are the whimsical things, like the pink elephant, the weather vanes that are so adorable. There are so many icons on the island that have so much meaning to the people who have been coming here their whole lives.” 

Rebecca Cleveland is now one of those whimsical icons of Boca Grande.