On most Saturdays during her childhood, MaryAnn Kai Kai would go shopping with her family on Rawdon Street in Freetown, Sierra Leone. Fashion was all around Kai Kai, who grew up admiring the vast closet of her grandmother, a diplomat’s wife. “She had all kinds of African prints and the latest fashions from the U.K.,” Kai Kai says.

Today, she makes custom caftans and dresses under the label Madam Wokie, a reference to her great-great-aunt Madam Wokie Massaquoi, a former member of Sierra Leone’s parliament who once met Queen Elizabeth. Kai Kai has shown her exquisite tie-dyed m’boubou gowns on the runways of New York and Lagos and outfitted Idris Elba, the Duchess of York, and the first ladies of Angola and Nigeria.

Kai Kai also strives to give back. During the pandemic, she launched a program to teach women to hand-dye cloth using the gara technique, which originated in Indonesia. The cloth patterns that Kai Kai uses often include cow’s eyes. Last spring, with the support of the Sierra Leone Economic Diversification Project, she helped train 800 women across the country to make batiks and beads. Today the women sell their wares on the beaches outside town and in the more remote Banana Islands. 

To explore Freetown’s creative culture, follow Kai Kai’s guide to the city. 

Where to Stay

“From the veranda of Cole Street Guesthouse, in the suburb of Murray Town, you can see the Atlantic Ocean, and the courtyard is full of fruit trees. “

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Where to Browse Art

“One of my favorite artists is Hawa-Jane Bangura, who has a by-appointment-only studio in Cockle Bay. Her work explores African history, culture, and identity, and she really plays around with colors.” (Above: I Am Not My Hair.) 

Where to Shop

“On Malama Thomas Street, you can find vendors selling tons of different fabrics, from Sierra Leone’s gara and kontri cloth to Ghanaian, Nigerian, West African, and even Dutch prints. I also like to browse carvings, beads, jewelry, and drums at Big Markit, on Lamina Sankoh Street.” 

Where to Eat and Drink

“At Cole Street Guest House, I order fresh juice, like ginger, mango, or hibiscus, the “ros bif” corn tacos, and the spicy jerk goat with plantains and rice. On weekends, everybody heads to the nightclub there, Warehouse, to dance and hear DJs. It has a mix of all ages. The owners are two sisters. Most of the staff, including the bouncers, are women.”

For something downtown, Crown Bakery does a great Sierra Leone–style jollof rice with fish, beef, and chicken. There’s also artwork for sale.” 

Where to Hit the Beach

“I always see locals out in the waves at Bureh, River No. 2, or Tokeh Beach (seen here), on the Freetown Peninsula. After a day in the sun, I like to hit Franco’s for lobster and oysters — the tables are right on the sand.”

A version of this story first appeared in the April 2024 issue of Travel + Leisure under the headline “All Eyes on Freetown.“