What It's Like To … Build a Travel Company Around Books

Jalisa Whitley is the founder of BOOKED Trips, a travel company that turns books into immersive journeys. Each trip destination centers a book, with meals, conversations, and experiences designed around its themes and lines on the page.

“Booked trips are where women get to go from the pages of some of our favorite books to the places they’re set,” Whitley tells OkayAfrica. “Each day is like asking, ‘how do we let this sentence live in the real world?’”

Since launching in 2022, BOOKED Trips has taken travelers to destinations including Mexico, Colombia, Ghana, South Africa and Morocco. Whitley’s approach centers books by marginalized writers and partnerships with local businesses and storytellers, with an emphasis on experiencing destinations beyond their most familiar tourist narratives.

“ I look for stories by women, authors of color, writers outside the Western mainstream, “ she says. “These are voices that don’t get the attention they deserve but are deeply rooted in where they’re from.”

This month, the company embarked on its 15th journey. The group is traveling to Nairobi, Kenya, and Zanzibar, Tanzania for its first itinerary spanning two African countries, inspired by Troy Onyango’s What Are Butterflies Without Their Wings.

Whitley spoke to OkayAfrica about how a childhood love of reading became a travel business, how she builds a trip from a book, and what it takes to travel without simply extracting from the places you visit.

This interview has been edited for length and clarity.

Jalisa Whitley: I like to say my first passport was in the halls of books.

I grew up in Geneva, a small town in upstate New York. I grew up Pentecostal, and we had church all the time. Our church was right across the street from the library. At some point, I learned that if I went to the library, I could skip Monday night prayer. So I went. Every week, I’d walk across the street and check out ten books. Through those books, I could see how other girls around the world lived.

As a child, I was a big Harry Potter fan. I also read Madeline. I didn’t have many books about other Black girls. I also wasn’t really reading stories set in places like Ghana, Nigeria, or Morocco. That part of my world didn’t open up through books until I got older. But those early books showed me different ways of being and little girls who were curious and exploring the world in a way that I wasn’t yet. It opened up a different way of being for me.

In undergrad, I studied abroad in Hungary and Romania; in grad school, I studied in Israel and Jordan. Since then, I’ve traveled to about 50 countries. For me, the connection between books and travel has always been about seeing new places and building a bridge between you and other people. When you’re reading a book, you feel connected to people you’ve never met. Travel, for me, is that same bridge in physical form.

During the pandemic, I was working as a director at a health equity nonprofit. I lost seven family members during that period. There was so much grief and not a lot of time or space to process it. I started asking myself, “Okay, what actually brings me joy?” It was books and travel.

Around that time, I was part of a virtual book club, and we were reading The Secret Lives of Church Ladies by Deesha Philyaw. There’s a story in there about Peach Cobbler. I remember thinking, “Wouldn’t it be so cool to go to Savannah, Georgia, pick peaches, do a peach cobbler-making class, and talk about this story?” And then I thought, “Wait a minute. You could do that with so many books.”

That was the seed of BOOKED Trips.

Our very first trip was in October 2022, to Mexico City. We read Like Water for Chocolate by Laura Esquivel and a group of seven women agreed to do it. It was very much an experiment.

Looking back, a lot of the most important pieces of BOOKED Trips were born on that trip. I realized how powerful opening and closing dinners are as bookends, and how important it is to keep the group at what I now call “the size of conversation.” Those early trips helped me understand the “magic sauce.”

[Today, each trip follows a structure.] Before you travel, you get the trip book, a playlist of the city’s sounds, and our room spray. This way, you have an immersive experience even before you arrive.

Our first night together is always a book club dinner at a local restaurant. Food is a great way to get to know a culture and other people because everyone loves to break bread. We also don’t start with, “What do you do?” We open our experiences with, “Who are your people?” As people share the relationships that make them feel most themselves, you start to hear: “Oh, these are my people too. I can lean in. I can trust this experience.” Then we have a full book discussion.

Every day after that, the food and experiences are inspired by quotes from the book. Sometimes it’s literally, “How do I take this one sentence and make a whole world around it for a day?” That’s the creative practice of BOOKED Trips for me.

I look for books that center marginalized voices…women, authors of color, writers outside the Western Hemisphere, small presses, and non-mainstream voices that don’t get the attention they deserve. I want books that are deeply grounded in their setting, that talk about food, culture, and music so you can feel the place on the page. Historical and cultural context is also really important to me because you never arrive in a place ahistorically. There are politics and histories and layers of culture that shape why you experience a place the way you do.

I also love a “messy” book. I like when there’s tension around the table, where people can’t wait to say, “I hated that character,” or “I will defend this character to the end.” Books that challenge your perspective or make you want to argue and discuss stick with you longer.

It took a little while before I let myself see BOOK Trips as more than a passion project. That turning point came in 2023, on a trip to Bogotá, Colombia, inspired by The Man Who Could Move Clouds by Ingrid Rojas Contreras. Up until then, most of our travelers were people I knew. Word of mouth had moved beyond the circles I knew. That's when it clicked: this is a real thing. People worldwide are willing to travel for this experience.

We run a Maya Angelou Scholarship, a travel scholarship that gives $5,000 toward our trips to one to three people a year; that year, we supported three travelers from Germany, India, and Mexico. And then there was another traveler on that trip who wasn’t on scholarship at all. Just seeing what the experience meant for those three women moved her so much that she decided to fund a scholarship for the following year. For me, moments like that make it really clear that what we do isn’t just about going somewhere. It’s about shifting how people see themselves, their creative work, and what’s possible for their lives.

On the trips themselves, the conversations go far beyond plot. Our groups are intentionally small, and we’ve had travelers from about 21 to 70 years old. I think that’s the gift of books because they give you a safe way in. You might start out talking about a character’s marriage, and then suddenly you’re talking about your own. Travel itself is awe-inducing. You’re seeing things, tasting things, and feeling things for the first time. Combine that with vulnerability and spending eight to ten hours a day together over a week or more, and it creates a kind of intimacy we don’t often get.

Africa has become a really important part of BOOKED Trips’ story. So far we’ve done Ghana, Morocco, South Africa, and now Kenya and Zanzibar. In South Africa, we started with Intruders by Mohale Mashigo and then did Born a Crime by Trevor Noah twice. In Ghana, we’ve run trips around Homegoing by Yaa Gyasi. For Kenya and Zanzibar, we’re using What Are Butterflies Without Their Wings by Troy Onyango.

A big throughline across the African trips is what they mean to our travelers, especially African Americans. For a lot of them, this is bigger than a trip. It’s their first time on the continent or a long-delayed return. There is this feeling of, this is a homecoming for me.

From the beginning, it’s been really important to me that BOOKED Trips not be extractive. Since we launched in October 2022, we’ve invested over $205,000 in local, community-based businesses like restaurants, hotels, guides, drivers, and artisans. I am always an outsider in the places we visit. I might go on research trips and design the container, but I did not grow up there. Storytelling is shaped by who gets to tell the story, and I don’t think I should be the only one.

I prioritize partnering with locally owned, women-owned, and Black-owned businesses. I’m always thinking about how we can keep our travelers’ dollars in the communities that make these places what they are. Travel as an industry is often built around big multinational companies and huge amounts of economic “leakage.” I want to support the people who make a place what it is, in a real way.

About three months before a research trip, I’m looking at potential hotels, restaurants, experiences, and local partners. When I arrive, I go in anonymously. I want to know what it's like as a solo Black woman traveling with you. What kind of stories are you telling? What’s the frame…is it colonial, or is it grounded in the people who actually live here? Who leads the experience? How immersive is it really? When I choose a partner, that’s when I reveal who I am and what I’m hoping to build.

From there, it becomes a co-creation. I’ll say, “This is the book I’m interested in.” And then I ask, “What am I not seeing?” That question is key. What are the things tourists don’t usually do but should? What are we missing about your culture? We go back and forth, tweaking the route and the experiences. Only then do I sit back down with the book and choose the quotes that will anchor each day.

All of this has changed the way I read. Sometimes I joke that BOOKED has ruined reading for me because I’m always thinking, “Could this be a trip?” I notice every mention of food, a specific street, or a historical detail. It’s harder to just read for fun, but it’s also made me a deeper reader. I’m constantly looking for the historical and cultural context under the story.

Travel, especially as a Black woman, has made me braver. I will get up and go solo almost anywhere in the world. Travel has taught me that I can navigate situations and find community anywhere. It’s also connected me to a lineage of Black women writers and readers whose work is shaped by movement, people like Maya Angelou and Marita Golden, who both wrote about their time in Ghana. When I moved to Ghana and eventually married a Ghanaian partner, those books helped me understand myself and my choices in a new way. It reminded me I’m not the first person to wrestle with these questions… I’m bringing my own spin to them.

As for what’s next, there’s one African destination I want to make happen: Nigeria. I feel like Nigerian writers are pushing out some of the best writing of the last decade. Lagos, especially, requires a particular type of traveler. I want to find the right local partner who can hold that city and that energy in a way that aligns with the company’s values. An experience connected to something like the Aké Arts and Book Festival would be a dream.