Holly Hennessey


Virtue, a 53' Hatteras Yacht, is Home at the Moorings in Bay Isles

Holly lives her life to the fullest, taking every opportunity to enjoy maximum time on the water at the Moorings Marina at Bay Isles.

She welcomed me with a chilled bottle of Prosecco, and when the cork was a bit stubborn, she quickly adapted by sabering the bottle with a handy sword she keeps for that singular purpose!  The secret to a clean swipe? According to Holly, it is finding the seam along the side of the bottle ... needless to say, it was a highly enjoyable visit and my very first interview accompanied by "the bubbly!"

Holly splits her time between Bay Isles, a condo in downtown Milwaukee, Wisconsin, and Destin, Florida, where she owns investment properties. When in Bay Isles, Holly calls her 1984, 53' Hatteras "Virtue" her home. She shares it with Captain, her Siamese cat. They live comfortably, tied up on C Dock, rarely leaving port.

Cruising is a lifetime passion for Holly. She jumped aboard big time in 1997 when she took an Around the World Cruise that departed and returned to Athens, Greece. The small ship still celebrates with reunions and a monthly newsletter. She also took a QEII World Cruise where at the last minute her plans for a cabin mate changed, and she agreed to share hers with a man she did not know before, a retired teacher and Methodist Missionary, who she calls an "Angel" and she now considers a life-long friend.

A boating inspired life offers opportunities, challenges and glorious vistas to discover close up. It amplifies your relationship with mother nature and creates memories to cherish forever.


About Sara Sinaiko

Sara Sinaiko is thrilled to be the Publisher of LBK Isles Life, believing that it represents a panoply of her life experience and skills.Sara has an entrepreneurial edge and calls upon her early career on Wall Street where she advised C-Suite Executives on Investment Banking options in the Public and Private Markets, her exposure to Philanthropic Organizations as a CEO and Executive Director, and her experience in Marketing Consulting. She also has lived and worked in Paris, France and Venice, Italy to pursue her love of fine art and culture.Ownership of the N2 Publishing Franchise for Bay Isles on Longboat Key, gives Sara the opportunity to turn the neighborhood into a community. Meeting the residents of Bay Isles and bringing them together to share stories and events makes it an exciting and varied professional challenge.For businesses that want to develop meaningful relationships with the residents of Bay Isles, there is no better way to reach them than through a Marketing Partnership with LBK Isles Life. It is a three pronged approach: Feature Stories, Events, and monthly Print Ads.Reach a most desirable Target Market in Sarasota/Manatee Counties - BAY ISLES on LONGBOAT KEYLBK isles life, is a monthly, lifestyle magazineOur Readers are well educated, discerning, maintain high levels of discretionary income, and have buying power. They are active, socially responsible, involved in local philanthropy as volunteers, and some serve on the Board of Directors of the most important nonprofits in the region, such as Save Our Seabirds, Mote Marine, The Sarasota Community Foundation, The Pines Senior Living & Rehab Center, The Selby Library Foundation, and they fully support our thriving Art & Culture Scene.They are C-Suite Executives, Business Owners, Renowned Academics, and Re-invented Retirees. Many own more than one residence, travel frequently, enjoy extended family and love their pets. They play golf, tennis, are boaters and walkers, enjoying the “good life” in Bay Isles.Contact Sara Sinaiko for Marketing Rates and Terms


  1. avatar Mandy Peterson on January 1, 2019 at 5:54 pm

    Dear Sara, nice article. So pleased to see my dear friend Holly was featured. Keep up the good work.
    I am a Longboat Key resident. I coordinate a Wed. am knitting group and a Sunday am ‘drop- in’ at the marina. Hope to meet you at one of these groups where you will meet other interesting residents.

    • avatar Sara Sinaiko on January 2, 2019 at 12:13 pm

      Happy New Year, Mandy! Thank you for writing. I look forward to meeting you and your friends. Do you have time for an interview? I’d like to learn more about your Groups. Please Reply with the best way to reach you. All the Best, Sara

  2. avatar Deb BGB on January 2, 2019 at 5:22 pm

    The World Cruise (Around the World) trip was mid-November 1999 to mid-March 2000, purposely timed to coincide with the millennium (which we celebrated in Buenos Aires). It wasn’t 1997.

  3. avatar Sara Sinaiko on January 2, 2019 at 8:39 pm

    Hello Deb, Thank you for the clarification. Sounds like you were on the World Cruise with Holly. How fortunate you both were to experience the new year of the millennium together in Buenos Aires. All the Best, Sara

  4. avatar Jim Snyder on January 3, 2019 at 10:30 am

    Nice article. Holly is a unique and awesome lady.

    • avatar Sara Sinaiko on January 3, 2019 at 5:11 pm

      Hello Jim, Totally agree. By any chance, are you the Jim Snyder who earned an MBA at UW- Madison ? It would be a small world story…. Best, Sara

      • Jim Snyder on January 4, 2019 at 10:42 am

        Hello Sara. I earned my law degree at UW-Madison so I must not be same dude!

  5. avatar Sara Sinaiko on January 5, 2019 at 9:00 am

    Hi Jim, UW-Madison does have a great Law School. Good to know a fellow Badger! I was with Holly last night for the Palm Avenue Art Walk and dinner. Always a fun time to enjoy Holly’s company. All the Best, Sara