Farming Heritage

Founded in 1978, Simpson Family Estates innovates for the future while honoring the past three generations of farming on the Leelanau Peninsula.


The Simpson family first planted their roots on the Leelanau Peninsula in the 1950s when visionary entrepreneur John Simpson grew pears and plums for Gerber’s baby food. In the 1970s, he replaced the trees with cherries when that industry became more marketable. John saw an opportunity for cool-climate wine and sent his son, Bruce, to study grape growing and winemaking at the University of California, Davis. 

Upon graduation, Bruce and his wife, Debbie, returned to the farm to start a family, plant vineyards and open a tasting room, slowly converting the cherry trees to grapes over the years as production and demand increased. He was instrumental in driving wine tourism in the Leelanau Peninsula as a founding member of several advocacy groups and associations. 

When Bruce died unexpectedly in 2009, his children Sam and Taylor Simpson returned home to advance the family business and growing operations. Together, the brother-sister team carry on the legacy of their father of producing affordable, quality wine; and of their grandfather in continuing to build family focused community and blue-ribbon early education.

About Us

Leadership Team

Meet the people behind every glass

Sam Simpson

Co-Owner, President

Sam’s entrepreneurial spirit started with a roadside cherry stand at age 7 and a successful landscaping business in high school. He harvested his viticulture and enology knowledge by working on the family farm with his grandpa and dad every summer while studying business and finance at Michigan State. Ever the innovator, Sam continues to fill gaps in the Michigan wine industry. He created vineyard operating services, now the largest in the state supporting 300+ acres, and launched the only mobile wine bottling service in the midwest.

Taylor Simpson

Co-Owner, Marketing & Sales

Taylor lived the city life in Chicago after growing up in Leland and graduating from the University of Michigan. She worked in wine sales distribution for the largest wine and spirits distributor in the world, honing her knowledge of wine and business while traveling to renowned wine regions of the world. She carried this extensive experience back home with her and continues to expand the reach of our wines through direct to consumers channels in 17 states (and growing!), boutique and chain grocery stores, and Midwest restaurants. She focuses her marketing efforts on building brands that convey a genuine story of the people and places behind the wines.

Drew Perry

Head of Production

Drew has created award-winning white, red and sparkling wines since joining the team in 2014 for Good Harbor Vineyards, then Aurora Cellars and a variety of custom clients. He has a pragmatic approach to making wine, modifying his philosophy with the ever-evolving growing conditions and weather year over year. Drew’s on a mission to surprise and delight the senses with every glass. Drew graduated from Michigan State University with a degree in Viticulture and Oenology, honing his craft in Napa before moving back to Northern Michigan.

Nick Florip

Vineyard Manager

Hailing from Leelanau County, Nick has always loved both the natural beauty of the area and industries that thrive in its unique micro climate. Upon graduating from Hope College, Nick moved back to the area as a site coordinator at a local non-profit specializing in invasive species removal and youth mentorship. This position was followed by a transition into operations manager for a local hop and high-density apple farm. This experience solidified Nick’s passion for agriculture and has led him to dive head-first into the world of viticulture. 

Jason Casares

Farm Manager

Jason Casares has lived on the Leelanau Peninsula for over 25 years and has worked for Simpson Family Estates since 2005. Throughout his career he has handled any and every job he has been given. He focuses his talents on farm management and mastering logistics of people and machines between multiple farms and clients. His knowledge of each farm along with mechanical skills and his welding skills help keep the farm running. Jason’s passion for viticulture is evident by his commitment to his job and his desire to push himself to succeed.


Wine Making

 Our winemaking team is made up of a dynamic group of professionals with a variety of backgrounds.  The cellar team works hard to ensure cellar standards are held to the highest degree.  With rigorous quality methods in place, the group works as a team to create some of the finest wines produced in Michigan.  The artistry of our barrel program, in addition to the highly aromatic white and rosé production, rounded out with the award-winning sparkling wines are all a result of the hard work of our vineyard team during the growing season and finished by this cellar team after harvest.  The passion this group of people have for their craft is evident when opening each bottle


Vineyard Production

Harbor Hill Fruit Farms, the custom services operation under Simpson Family Estates, employs nearly two dozen workers. They work hard cultivating the vineyards for nine months, returning each year to help us grow, maintain and harvest hundreds of acres of grapes. Simpson Family Estates value the sacrifice these gentlemen have made to be in Northern Michigan to work with us. Their invaluable contributions are recognized day after day and never taken for granted. We are a company that values family, hard work, and respect for others. We thank these gentlemen and recognize their immense contribution to the wine industry.