As a freckle-faced California girl with roots in Texas and Louisiana, I always assumed those states were the extent of my family’s lineage. I’d never tried to trace where we originated in Africa before slavery, but I was given an unexpected surprise last year. After a family reunion on my grandfather’s side, my mother sent me a new family tree that included a great-great grandfather who was from the West Indies. Word? All of these years I’ve attended Brooklyn’s West Indian Day Parade and could’ve been waving a flag for St. Kitts or St. Croix? Boo!

Lucky for me, earlier this summer I headed to the island of my ancestors to investigate our family history for myself thanks to the St. Kitts Marriott Resort and Beach Casino. The airy resort, complete with ample coastline, poolside restaurants and plenty of activities, provided the best amenity of all: a personal history tour of the country by Marriott public relations director Lavern Stevens. She even told me some scary stories, and suffice to say, I’m not walking through Independence Square in the capital city of Basseterre alone or at night. Ever.

In downtown Basseterre (thanks to Lavern’s connections), we walked right into government headquarters and the country’s official records office to track down my great-great grandfather, Smith Wilkerson, and his lineage. The family history I had asserted that his Wilkerson clan were most likely from St. Kitts or St. Croix, and Lavern asked if we were related to the wealthy local family, the Wilkinsons.

I had no idea.

But as we dug through the records with Victoria O’Flaherty, director of the St. Kitts National Archives, and her excitable assistant, I discovered that I might be. Census records from the 1800s are pretty spotty—especially because many people couldn’t read or write, so the spellings of names fluctuated over time. One might begin as a Wilkerson, but become a Wilkinson because, you know, who needs an “e” or an “r.”

In this case, one might also begin as a Wilkes and become a Wilkerson, because one might literally be Wilkes’ son. In the records, we found a number of Wilkes and Wilkersons, but none named Smith. Still, the people we might’ve identified could’ve been Smithes’ brothers or sisters. According to the records office team, I must now head to St. Croix to investigate my family’s records further.

After that exhilaration (have I mentioned I’m an African-American studies major and huge history nerd?), Lavern and I walked down to Independence Square, where the enslaved Africans were auctioned during the slave trade. The houses that line the square were former slave owner homes, complete with slave quarters. Lavern said a friend had converted one of these homes into an office, and found slave quarters in the basement. As she worked late nights, she could hear chains rattling, though there were no metal remnants of her ancestors. Lavern’s friend eventually poured concrete over the slaves’ quarters, since she wasn’t about that life.

Elsewhere, in the actual Independence Square, Lavern said her grandmother told her stories of people walking in at night and not being able to find their way out. Independence Square is only about one-fourth of a New York City block, so it’d be tough to get lost. But legend says the spirits of old slaves who couldn’t escape the Square thanks to the flesh trade passed that feeling on to the living. Needless to say, I scurried out of Independence Square.

Continuing our tour, we walked down to Port Zante, a cruise ship dock lined with tourist trap shops full of clothing, jewelry and freelance masseuses. (Seriously, there was a kid who popped up at several different places we ventured, carrying some aloe plants and oil like, “I got them hands for cheap!” I declined.) Between the T-shirts and bathing suits, it’s tough to tell this area was where the African slaves were transported onto the island of St. Kitts before they were shuttled to Independence Square. But realizing Port Zante’s history was eerie, especially when some of them could’ve easily been my ancestors. The experience didn’t make me want to buy a T-shirt, I’ll tell say that.

Later, we headed to Brimstone Hill Fortress National Park, a stone structure designed by British engineers and built by African slaves in 1690. British troops fought many battles with the French over sugar cane at Brimstone Hill. But after the Treaty of Versailles, the fighting ended and the Fortress was eventually abandoned in 1852. Now the Society for the Restoration of Brimstone Hill have returned the Fortress to its previous glory, including historical presentations and a few mannequins dressed like soldiers and positioned in dark corners that scared a scream out of me. It’s hard to retain your cool when you round a corner and what looks like a dead man is lying on the floor of a dark museum hallway... Then you feel like an ass because it’s a mannequin with a sketchy wig.

Ultimately, I enjoyed St. Kitts, even though I didn’t get to the island of Nevis for a Killer Bee rum cocktail at the Oualie Beach Hotel bar—a haunt of celebs like Jay Z and Beyoncé. Hopefully my mom and I can make a weekend trip of finding our roots in St. Croix, and then perhaps apply our findings back in St. Kitts. I have to get to the bottom of what flag I should wave at this year’s West Indian Day Parade. Labor Day is fast approaching!

Hillary Crosley is a journalist and the co-founder of Parlour magazine, an international website for women of color. Follow her on Twitter @HillaryCrosley.