Today we’d like to introduce you to Siobhan Cleveland.
Hi Siobhan, can you start by introducing yourself? We’d love to learn more about how you got to where you are today.
It’s been an interesting and unexpected journey becoming the owner of The Real Macaw, a Key-West-inspired Restaurant and Bar in Naples. I started my career in the fashion industry after founding a line of handmade tutus in Charleston, South Carolina while attending the College of Charleston. That business turned into opportunities that took me to New York where I worked odd jobs like hosting a show for New York Fashion Week and having a few “Devil Wears Prada”-esque internships before discovering a love for the wholesale side of corporate fashion.
Working with couturier Maggie Norris, and hat designer Eugenia Kim, and as Roller Rabbit’s Director of Wholesale enabled me to work with buyers from all over the world with storied brands like Net-A-Porter, Bergdorf Goodman, and Saks Fifth Avenue. In my spare time, I volunteered at the Metropolitan Museum of Art and took comedy and ballet classes in Greenwich Village. It was a fun time to be in the city and my work introduced me to so many wonderful and talented designers and friends, along with providing the chance to be creative and learn the excitement that comes with building a business.
When the pandemic began, Manhattan quickly became frightening. Unsure of how dire the situation would become, my husband and I decided to visit my mother, Jeanne, in Naples, Florida for a few weeks “while the whole thing blew over.” As we know now, that was wishful thinking and it took over 6 months for us to return to the city and temporarily at that. During that time in Florida, we sadly came to find out that my mother, who was the founder and original owner of The Real Macaw, was terminally ill with lung cancer. Concerned for her health, I took over operating the restaurant so she could remain home resting and healing.
As my mother’s illness progressed, we made a permanent move to Naples and when she sadly passed away in March of 2021, the ownership and operation of the restaurant fell to me. Those who knew what a fabulous, funny, wonderful woman she was would have appreciated what big shoes those were to fill. It’s not the average person who would create a place like The Real Macaw! As I dug more into the business, I realized the fundamentals were very similar to my last career- inventory, product development, storytelling, and, most importantly, people. I also heard day in and day out from customers and the community how important this place was to them, how much it mattered, and how much they loved it.
My thoughts toward it as an unexpected burden began to shift too. I appreciated its uniqueness and the opportunity it provided to be creative, to use my skills and experience to put into action Mom’s ideas she had run out of time to execute and to layer in my vision with new cocktails, menu items, and design elements. With the support of my husband, staff, and customers, an exciting new chapter for this very special place began to reveal itself. And, as if life was not full of enough twists and turns, we had recently found out we were expecting our first child, a girl, and were looking toward a new beginning after such a heartbreaking loss.
During this time, I was enrolled in a Master’s program in Strategic Design for Global Leadership at Parsons The New School. Collaborating with an amazing cohort of international classmates and faculty like David Schreff, a former NBA and Disney executive, and Johann Verheem, a seasoned investor, helped inform the work I was putting into the restaurant. As I had learned in fashion, it’s all about the customer and how to use design and intention to give them the best experience possible. Providing that through a special ambiance, service, and food is my goal every day.
We hit our stride for a season when Hurricane Ian landed last October 2022. In 32 years the business had never flooded. This time we unfortunately weren’t so lucky. The restaurant was inundated with 4 feet of water, so high it floated our signature floral plates off the table tops (which miraculously did not break), and the devastation it wrought was beyond anything I had ever witnessed. In addition to the property, many staff were displaced and the entire neighborhood looked like a war zone with the entire contents of people’s homes and lives piled on the curb.
We were fortunate to have a great team in place and I, my husband, our general manager, staff, and even our musicians rolled up their sleeves to help put The Macaw back together. Moving quickly, we demoed the place down to the studs, sanitized, and reopened outdoor spaces within 3 weeks with a limited, hand-written menu just to feed those who had no kitchens left. The community was so supportive and after non-stop work, our dining room reopened for Thanksgiving of that year. Repairs continued but in many ways, a refresh after 30 years wasn’t the worst outcome. The Real Macaw looks more beautiful than ever, an unimaginable feat when we were wearing headlamps and rain boots cleaning up the mess.
Today, the Macaw continues to thrive with the help of an incredible General Manager Chris Loper, an alum of the Forum restaurant in downtown Boston, our Bar Manager Olivia Bennett who makes the meanest margarita in town, and a fabulous team in the kitchen and on the floor who put so much love and care into their work. It has been a very unexpected career change to be back in the family business and living in Naples instead of NYC. Every time we hear a positive word from a customer, see someone return or get on their feet and dance because the music is just too good, I understand why mom loved this place and it brings me just as much joy.
Likewise, I’ve discovered the restaurant can be a great way to stay connected to my fashion roots. I’ve continued to work with Erica Wilson, a lovely boutique on Main Street in Nantucket, as a consultant to assist them in brand building and designing a line of exclusive Nantucket-inspired pajamas and block-printed sundresses. We’re hosting their first Trunk Show in Naples this February and I’m so excited to have my favorite clothes in my favorite place.
It’ll be hard not getting one of everything!
As you know, we’re big fans of The Real Macaw. For our readers who might not be as familiar what can you tell them about the brand?
It’s hard to capture in words what a truly magical place The Real Macaw is. I love seeing the look on people’s faces when they walk in for the first time, it’s sheer awe and delight. The space is awash with bold colors, vibrant artwork, palm trees, and big rattan peacock chairs. At night, cafe lighting, torches, and live music further add to the ambiance of a hidden island hideaway. As unique as the atmosphere is, our food is what truly sets us apart. Executive Chef Tebah Brewley is like family, having worked at the Macaw for over 30 years.
Originally from Tortola with stints in Cape Cod and Nantucket, his ability to create new and memorable flavor combinations is a true talent. While every dish on the menu is worth a try, favorites include our jumbo lump Trinidadian Crab Cake with a chipotle remoulade and our Caribbean Duck, decadently crispy with a Tamarind Rum sauce. His seafood is off the charts too whether it’s the Scampi with fresh egg noodles, sauteed shrimp, and scallops, or the Dayboat Catch, which offers Chef the chance to bring in the freshest seafood and experiment with new concepts. Last week’s Dayboat was a Poached Red Snapper with Crawfish Etouffee that was to die for. Everything we make is from scratch including our famous Key Lime pie, and we just added a Carrot Cake based on a 100-year-old recipe from one of our servers we can’t seem to make fast enough! Our Bamboo Bar, which has its menu, is known for its Bacon Cheddar burgers, made with Wagyu Kobe beef I pick up weekly from the best butcher in Naples, Jimmy P’s.
To complement the cuisine, we have a boutique wine list with unique offerings you’ll only find with us. A must-try is the Sancerre. This crisp white is perfect year-round and is especially perfect when paired with seafood. And of course, no island bar would be complete without cocktails! My favorites are the Caribbean Cosmo made with Kettle One Peach and Orange Blossom Vodka which gives it a great flavor without being too sweet, Olivia’s Paloma made with freshly squeezed Ruby Red Grapefruit juice and tequila, and the Old Town Old Fashioned with Templeton Rye and Woodford Bourbon Cherries. (Our Espresso Martini is always a hit for dessert.)
The cherry on top of a night out at the Macaw is the incredible lineup of musicians we’re fortunate to have grace our Macaw stage. Notable artists include Sonny Kenn, a rockabilly blues buddy of Bruce Springsteen who brings the house down every time he plays, Kelly Neff, an award-winning singer-songwriter traveling from her home in Southwest Florida up to Nashville on the weekends to record an album, and Frank Corso, an accomplished downhome blues musician whose steel guitar stylings get every toe in the place tapping. Music has always been an important part of what we do and we’re so thrilled to showcase live music nearly every night of the week, with a special Winter Concert Series to launch this January and February.
We all know those great restaurants that are more than the sum of their parts. They become a community hub, the start of a great story, and a place where you always feel welcome and at home. I feel so fortunate and proud to be the owner of one such establishment at The Real Macaw. I hear daily from returning guests about their fond memories spent here and from first-time visitors, how thrilled they are to have discovered a new hidden gem. With each year places like ours, a true throwback to old Florida charm, become harder and harder to find. The irony is that our retro vibe is now more popular than ever and we’re seeing an influx of new, evermore stylish, and cosmopolitan customers.
It has been an endlessly rewarding journey working with our staff and friends to recover this landmark from Hurricane Ian and make it shine while preserving its unique, eclectic character. We’re currently working on an exclusive Real Macaw ice cream flavor from popular new Naples shop Fernweh, a line of branded merch and we’re bottling Chef’s killer hot sauce (another thing we couldn’t make enough of!). With 32 years of heritage behind us, the future of The Real Macaw looks even brighter. I’m excited to see where the road leads next and to continue to welcome guests to this little piece of paradise as we honor my mom’s legacy and start to build our own.
Contact Info:
- Website: https://www.therealmacaw.com/
- Instagram: @realmacawnaples
- Facebook: https://www.facebook.com/therealmacawnaples/
