Spotlight on Cindy Shannon – Creativity & Collaboration Are the Hallmarks of This Island Girl’s Hawaii Life

Born in Hinsdale, Illinois and raised with Midwest values in the western suburbs of Chicago, Cindy Shannon is what you might call a successive entrepreneur. Lured by an appreciation for great design, she gained early experience with luxury brands and an affluent clientele while pursuing her passion for cutting-edge fashion and clothing design. But a desire to feel more grounded and to live a more authentic life led her to the simplicity of island living, first in the U.S. Virgin Islands and then later in Hawaii, where she settled permanently North Shore of Kauai.

Cindy was making waves in the U.S. Virgin Islands on one of her tour boats.

The Ebb & Flow of Island Life

Following her studies at The International Academy of Design and Technology in Chicago, Cindy moved to St. Thomas. In the Caribbean, she says found her soul. “Island life in St. Thomas stripped all away and left behind what was raw and real,” Cindy told us. There, she met her husband who encouraged their first move to Kauai in 1995. Cindy’s husband captained Zodiac boat tours of the Na Pali Coast over those first three years spent living on the North Shore, where their only daughter was born.

They later returned to the Virgin Islands, now married, and with a daughter to launch a tour boat company tailored to the cruise lines and resorts. Their company launched with “a bang and a buzz”, dominating the local market and winning awards as they built successful relationships with brands like the Ritz-Carlton, Norwegian, Princess and Royal Caribbean Cruise Lines.

They also started a surf wear store on the island. Cindy handled the marketing and promotions, concierge services,  staffing, tour itineraries, and public relations for their businesses. Her passion for design made buying and curating items for the store a breeze. With both businesses going full throttle, they found balance in the pace of island living.

A television appearance in Florida, where Cindy promoted her successful spa and wellness center.

Family matters spurred a move back to the Suncoast of Florida. While homeschooling her daughter there, Cindy launched yet another successful enterprise. Fully engaged, Cindy became a licensed health care practitioner so she could better manage her day spa and wellness center, where she offered leading-edge spa services, holistic healing arts, and innovative, hard-to-find wellness products. Despite her success, the desire to return to Kaua‘i remained strong. Cindy sold the Om Shoppe & Spa for a profit and it’s still thriving today, as is her boat tour company in the Caribbean, under new ownership.

The Magic & Mana of Hawaii

Cindy made a permanent move to Kauai, bringing her family, her considerable business acumen, and her entrepreneurial spirit to the islands. Her travels had unearthed a deep appreciation for what she describes as “the magic and mana of Hawaii”. Kauai’s powerful energy was something she says she was unprepared for on her first stay back in 1995, but something she cherishes today.

Inspired by the island’s abundant natural beauty and the creativity of those around her, Kauai has proved a perfect fit. The place resonates with her spiritual side. “I believe it is through our creative works that we come the closest to knowing the Creator itself. I live to be inspired and to inspire others,” Cindy said.

Her creative spark manifests itself in home improvement projects, time spent meditating in her gardens and preparing living foods cuisine for friends and family. A natural athlete, in her free time Cindy hikes, paddleboards, practices yoga, cycles and plays golf and tennis. Her recommended trails on Kauai: Kalalau (pictured at top) and Mahaulepu. A voracious reader, she keeps on top of the latest advancements in holistic health & wellness, sustainable living, and of course, she reads avidly about real estate. She’s currently engrossed in Ray Dalio’s Principles.

“When in resonance with something, energy becomes amplified and we feel more powerful and strong,” Cindy says of her life on Kauai.

A Love of Sustainable Living & Design

On Kauai, Cindy has embraced a vital movement afoot that’s focused on sustainable property and community development, using the latest innovations in materials and design. With so much natural beauty worth preserving, Kauai is the perfect place to set a forward-thinking and sustainable example for responsible growth and development that other communities can follow. She told us, “I feel called to be in the middle of it with Hawaii Life.”

Cindy loves Kauai’s eco-friendly mindset. She points to the Kukui’ula Resort, a 1,000-acre master-planned resort residential community on Kauai’s south shore, which maintains its own 10-acre, upcountry organic farm. The Aloha ʻĀina Project and their progressive work at the Hawaiian Sustainability Foundation is another source of inspiration for her.

She brings a deep appreciation for architectural, interior and landscape design to her role as an agent. “I started reading Vogue and Architectural Digest in middle school, and those publications still grace my space,” said Cindy. She also brings plenty of experience in buying, selling, renovating, building and investing in real estate to the table. “I enjoy being in the energy of creative inspiration,” says Cindy, whose pastimes include driving around the island looking at homes and their architecture.

Cindy’s Approach to Life & Business

We asked Cindy about her approach to her relatively new real estate practice. “I am excited to turn what has been a passionate hobby into a career and to use all of my experience to redefine what excellence in service, innovation and development can be,” she told us. Cindy believes strongly in the value of collaboration to achieve goals and welcomes the opportunity to partner with others agents across the organization, to build a stronger network. “I believe there is strength in numbers when you partner with the right people who are all dedicated to reaching the same goals, with shared values and professional ethics. Harmony is important for creating something magical that uplifts the entire group dynamic,” she shared.

“I live a private life that I am deeply grateful for and a professional life that is rich and rewarding for my clients, as well as for myself.”

Cindy acknowledges that our homes are our sanctuaries and retreats, the castles where we get to reign as kings and queens of our private domains. She believes they are the places where we prepare ourselves to take on the challenges of life and where we invest in our futures. Selecting the perfect property is a big deal, no matter the price tag, big or small.

When it comes to selling a home, Cindy’s wealth of business experience lends itself seamlessly to this industry and to the luxury market. “I am a natural at staging and identifying who the market is for a specific property and knowing how to attract buyers,” she said. “I thrill to the challenge of image marketing and making matches with clients and customers through skillful staging and strategic photography,” she added.

Why She Chose Hawaii Life

Cindy was attracted to Hawaii Life’s reputation for being on the leading edge of the industry and technology. “I am impressed with how well they stay ahead of the curve and strive to function as a high-performance body, seemingly without effort,” Cindy said. This resonated with her since she credits her own similar leadership mindset to the success of her many previous ventures. “I thrive in being a part of making peoples’ visions, hopes and dreams a tangible reality,” she added.

She was also impressed with what she terms Hawaii Life’s “heart and soul” – the company’s philanthropic care and concern for the islands through corporate giving and the Hawaii Life Charitable Fund, which supports local non-profits through grant funding. Regarding Hawaii Life’s commitment to giving to the community, she said, “I believe in reciprocity. Hawaii Life is exemplary at this – from their charitable fund to their volunteer outreach in times of need, to their creation of Conservation and Legacy Lands management, directed by Beth Thoma Robinson R(B).”

Given her background working with luxury brands, Cindy was also drawn to Hawaii Life’s statewide affiliation with Christie’s International Real Estate. As the world’s leading luxury real estate brand, Christie’s global span and expertise extend to more than 138 affiliated brokerages in 46 countries. Hawaii Life is the only U.S affiliate to represent an entire state. This key brand association, as well as Hawaii Life’s consistent and quality company branding, impressed Cindy, who understands the importance of brand alignment in people’s buying decisions. She enjoys matching buyers with the perfect homes and rejoices when they say, “That’s the one for me!”

To learn more about Cindy Shannon and her Kauai life, her unique approach to her business, and listing, please view her webpage. To learn more about her entrepreneurial spirit, you can check out her LinkedIn profile. You can email Cindy at or call her with your real estate inquiries at 808-464-7471.

“Put my alchemy to work for you and let’s make magic happen!

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