Cassandra meets wine legend Iris Duplantier Rideau, the first Creole woman to own a winery in the United States. From growing up in Jim Crow to becoming a pioneer in various industries, Iris's story transcends decades of history. Sharing her story and mentoring others like Jason McClain, Founder of McClain Cellars cements her legacy as a trailblazer, bridging the gap for women and BIPOC industry hopefuls.

Cassandra connects with the McBride Sisters, one of the largest Black-Owned wine companies in the United States. Their success and dedication to paying it forward inspired women like Fern Stroud, Founder of Black Vines to lean on her sisters to create an ecosystem of community, culture, and sisterhood.

Cassandra experiences Napa, visiting James Moss, Founder of J Moss winery. Joining her is Tonya Pitts, sommelier who shares her wine skills. Cassandra also embarks on the ride of a lifetime with the picturesque Napa Valley Wine Train ride.

Spend a day with Cassandra as she visits her favorite spots in San Diego. From a woman-owned brewery in Barrio Logan to a East Village wine bar, and the Rady Shell at Jacobs Park, Cassandra indulges in San Diego tourism.

Garden 31, created by Chris Burroughs brings agriculture to urban communities to eradicate food deserts, create job training programs, and educate future generations. With the help of University Agriculture and Natural Resources, Chris's mission will thrive, inspire, and set an example of the possibilities.

Cassandra travels to Mexico on an exclusive trip courtesy of Baja Wine & Dine Tours. Ultimate dining experiences, wine and tequila tasting, and a visit from the queen of ceviche, Cassandra and her friends get the VIP treatment.

Cassandra's journey in Mexico continues. Visiting Valle de Guadalupe and Ensenada, Cassandra dance to the beat of her drum soaking up the Mexico culture.

Cassandra visits Oregon for the first time. Spending time in Willamette Valley Wine Country, Cassandra falls in love with the stories of the Maysara and Cho Family. Incorporating culture, the history of winemaking, and bio dynamic practices, both families created a legacy of love to share with the world.

Back in her east coast roots, Cassandra visits Philadelphia and New York to connect with family and friends. She visits Marvina Robinson, Founder of B Stuyvesant Champagne and mentor, sommelier, restauranter, and YouTube phenom, Andre Mack. Reconnecting with her friends and roots, Cassandra pays homage to the culture.