Nadia "Sparkle" Henry
For generations, Martha's Vineyard, particularly the town of Oak Bluffs, has been a cherished vacation haven for the Black community. Its story is deeply rooted in African American history, resilience and culture.
The first African presence on the island dates back to the 1600s and 1700s, when enslaved Africans were brought to the Vineyard to work on farms and in households. By the 19th and 20th centuries, the island began to transform into a true refuge. Oak Bluffs became one of the few places where Black families could enjoy leisure without fear of exclusion.
One of the most pivotal figures in this legacy was Charles Shearer. Born enslaved in Appomattox County, Va., in 1854, he went on to graduate from what is now Hampton University. His wife, Henrietta Merchant, was born free in Lynchburg, Va., in 1859 and also attended Hampton, later serving as a school matron. The two married, moved to Massachusetts in 1891 and eventually fell in love with Martha's Vineyard after attending church services in Oak Bluffs.
In 1912, Charles and Henrietta established the Shearer Cottage, the island's first inn created specifically to welcome Black guests who were not accepted elsewhere. The Shearer family continues to operate the inn today.
My own family's connection to the Vineyard began more than 35 years ago, when my aunt, Dr. Sharon Henry Woodby, and my uncle, Joseph Woodby, discovered Oak Bluffs. During a Cape Cod vacation, they noticed the lack of Black travelers and decided to take the ferry to Martha's Vineyard. The moment they arrived, they were surrounded by a thriving community of people of color.
That discovery began a family tradition of annual visits, eventually leading to the purchase of property directly across from Inkwell Beach, a site once derisively named but now celebrated as a proud symbol of Black culture and resilience.
Today, Martha's Vineyard thrives as a vibrant hub for thousands of Black vacationers. Comedy shows, film festivals, day parties, fireworks, cultural events and networking mixers fill the summer calendar. The months of July and August, in particular, are when the island pulses with energy, tradition and community spirit.
One of the greatest challenges for visitors, however, is securing a place to stay. Martha's Vineyard has limited accommodations, with only a handful of hotels and inns. Most visitors rent private homes, which are typically offered only in weeklong increments.
Martha's Vineyard is a niche destination, and having insider knowledge is essential for curating the right experience. Beyond myself, only a select few travel advisors specialize in the Vineyard. One such expert is Ayasha Sameh Teague of Blueprint Travel, whose family also has a long legacy on the island.
Nadia "Sparkle" Henry and Jazzmine Douse, senior director of national accounts at Amawaterways. Photo Credit: Nadia "Sparkle" Henry/Travel with Sparkle
Recognizing the Vineyard's influential Black community, I partnered with Jazzmine Douse, director of national accounts at AmaWaterways and the visionary behind Ama's Soulful Experiences sailings, to showcase this groundbreaking product at the Martha's Vineyard African American Film Festival and at a fundraiser for Debbie Allen's Dance Academy.
These river cruises highlight Black history, culture and cuisine.
And truly, what better stage than Martha's Vineyard, a destination that has long celebrated Black excellence, culture and community, to introduce thousands of affluent travelers to such an offering?
My agency was honored to represent AmaWaterways in this initiative, which not only brought visibility to Soulful Experiences but also served as a powerful reminder of how networking opens doors, builds bridges and creates lasting opportunities. It was a full-circle moment: standing on an island rooted in Black history while helping shape the future of Black travel.