A warm breeze carried the scent of grilled fish and sea salt as we swayed to vibey Indonesian R&B, ocean waves echoing peacefully in the distance. We smiled, none of us knowing the words since they were in another language, but the feeling was instantly familiar. It was the perfect scene for a first night in Bali. Just hours earlier, we had brushed off jet lag, haggled for spices in a crowded market, and laughed through a bumpy van ride as one traveler retwisted another’s loose braids. They had only met that morning.
That night at dinner, tears welled in all our eyes as one traveler shared it was her first vacation alone in nearly twenty-five years, fresh from a painful divorce. But she was far from alone, surrounded by fifteen other Black women and me.
By the end of the trip, she pulled me aside and said, “I’m starting to feel like myself again.”
This is what traveling with Black women often feels like: magical, sometimes raw, but always beautiful.
For the past ten years, I’ve lived at the intersection of passport stamps and jasmine-scented welcome towels as the founder and host of Dipaways, a travel company curating refreshing global experiences. I’ve had the pleasure of guiding travelers through some of the world’s most beautiful corners, but nothing has moved me more than hosting Black women. From Accra’s lively, sun-kissed streets to the lush seaside cliffs of the Amalfi Coast, traveling alongside Black women from all walks of life has reshaped how I view the world and myself.
What I’ve learned is that these journeys are never just vacations.
They are mirrors. They are catalysts. They are the reason this work became something deeper. These women turned a business into a calling.
I’ve traveled with hairstylists and NASA scientists, food chemists, models, doulas, influencers, doctors, lawyers, bartenders, record label execs, adult content creators, athletes, stay-at-home moms, ministers, and even a few celebrities. The list goes on. The point is, Black women have range.
Over the years, I’ve listened to Black women share why they travel, and I’ve learned that those reasons often evolve along the way.
Some come to celebrate a win. Some arrive solo after life has shifted in ways they can’t yet name. Others come hand in hand with a partner or best friend. Many are traveling for the first time in years, and some for the very first time. A few arrive with no reason beyond seeing the trip online. Many carry their spirituality. Some bring their skepticism. I see designer luggage, and I see carry-ons paired with nothing but a prayer. Some lean toward culture, others toward adventure, and a few toward neither. What ties them together is curiosity for something deeper, a longing to feel safe, and the hope of a true pause. What they often discover, in the space they carve out for themselves, is that softness and strength are not opposites. On the trip, in that very moment, they are free to hold both.
Traveling while Black carries its own layer of invisible negotiation. There are questions of safety, of being seen, of being othered or exoticized. For many of the Black women I’ve hosted, vacation is rarely just vacation. It is a rebellion. A reset. A return to self.
Through Dipaways, we create space where it is safe to exhale. From the moment I meet our travelers at the airport, I am keenly aware of everything they carry. The nervousness, the excitement, the weight of their daily lives. Many mention how eager they are to shower and freshen up after traveling halfway across the world, but I still greet each with a warm hug and smile. What matters most is their willingness to show up. I take their bags. Learn their names. Give them room to settle and start to relax their nervous system.
On these trips, I float through many roles: business owner, tour leader, personal concierge, cultural interpreter, playlist master, and sometimes a very unofficial but helpful on-the-low type of therapist. One moment I’m explaining why a five-star hotel has no running water. The next, I’m sitting quietly on a yacht at an all-white party beside a woman navigating an unexpected period. Some nights they pull me in as a friend, offering rounds for everyone and dancing until sunrise. And in the early hours, the front desk calls to let me know a guest is in tears, missing the child she left behind for her first true vacation.
And still, there is laughter. There is always laughter.
One of the most beautiful things I have witnessed is the bond formed between women who arrive as strangers and leave as something closer to chosen family. Women in their thirties doing full-on choreo to Beyoncé’s Renaissance album with women in their seventies. Extroverts bringing moments to life with laughter and commotion. Introverts showing the group how to slow down and listen more deeply. I have watched a shy woman from Detroit receive affirmations from an entire group of new sisters, her face softening with every toast. I have watched women encourage each other to wear that dress, take that photo, try that food, go on that date, and jump into that water. And they usually do.
A few years ago, we hosted a desert mindfulness experience in Joshua Tree, California. It was our first wellness-centered trip, designed for reflection, quiet joy, and healing under the stars. The trip was open to everyone, but only Black women booked. There was something poetic about that. In the scorching stillness of the desert, surrounded by dust and silence, we created something alive and refreshing. Ironically, I was not in the best place myself. My personal life was rocky, and I had nothing left to give. I was exhausted. I did not know if I had it in me to show up with the kind of heart I normally bring.
So I called on someone who had held me before. A close friend, a Black woman. She showed up without hesitation. She helped organize activities, shop, prepare meals, clean, and even captured the whole week as the photographer. Her presence was not just helpful. It saved me. And in turn, it saved the experience. Thank you, Rashida.
All of the women who joined that experience were searching for something. Release. Connection. Peace. But in the end, they unknowingly poured into my emptiness by simply being. I watched them sing by the fire under the stars, meditate beside gigantic prickly plants, and journal in silence as tears slowly fell.
There is a quiet and radical beauty in it all. No matter their background or beliefs, these women find each other in the midst of it. Joy becomes the shared language.
I will never forget watching the reactions of locals in Italy. The Amalfi Coast loves Black women. The men are fascinated. They are stunned by the beauty, the confidence, the presence. I have seen waiters stop mid-order just to ask how each woman has a different hairstyle. They marvel at the braids, the twists, the wigs, the curls, the edges. They ask questions. They fall in love a little. And the women? They love the questions. They love being admired. They love being seen. It’s deserved.
Being the only man in a group of women brings its own dynamics. Sometimes it’s funny, sometimes I stay quiet knowing I won’t have backup. Over time, I realized these journeys weren’t just about leading trips. They were also about settling fully into my own identity as a man. Black women, when met with honesty, make space. There’s a grace they offer once they trust you, when they see you’re not performing but simply showing up as yourself.
Some of our most meaningful conversations have unfolded in hole-in-the-wall gems most people would walk right past. Dim lights, peeling paint, no AC, the smell of something fried in the air. Over shared plates and infectious cackles, we’ve swapped stories, cracked jokes only we would get, and touched on love, identity, and the freedom to be who you are, fully.
The beauty of these experiences goes beyond what we see to who we become. I’ve watched women who were quiet their whole lives lead the group in a sunrise meditation. I’ve seen content creators put their cameras down to dance barefoot under the moonlight. I’ve felt burnout melt from the shoulders of mothers rediscovering their sense of self. I’ve stood beside a woman celebrating her first birthday after beating breast cancer. These trips remind us what it feels like to truly live, not just survive.
And while I have hosted guests of all races and backgrounds, this particular reflection is for the Black women. They are the pulse. They are the ones who trusted Dipaways from the beginning. Who built this with me. Who show up for each other and the world, often with little recognition. They deserve experiences that are thoughtful and luxurious. They deserve joy that does not come at the cost of their peace.
Black women want to feel safe. Respected. Cherished. They want to dance. To rest. To be well fed and well cared for. They want good playlists, even better drinks, and freedom from the weight they carry back home. And we create space for that. We try, with every itinerary, every small detail.
Vacation tends to bring out the best in people, so I have seen very little conflict over the years. When issues arise, it is often rooted in fear or frustration with something outside of anyone’s control. Flight delays. Lost luggage. A hotel power outage. I have been cursed out once or twice, but more often than not, I have been met with empathy. Because Black women are understanding. And when you lead with care, they extend it back.
Some trips are loud. Others are soft and introspective. Some women come to turn up. Some come to heal. Many arrive in transition, whether it is a career shift, a fresh heartbreak, an empty nest, or simply a quiet yearning for more. Some are celebrating milestones. Others are grieving in silence. That longing connects them. That is where the power lives.
What I’ve learned most is that Black women are not a monolith but a mosaic. They are textured and vibrant, expressive, soft yet determined, observant, loyal, and deeply present. Very unserious when they want to be. Quiet when it matters, curious, spiritual, open-hearted. No two are the same, yet they reflect one another with a tenderness I rarely see elsewhere.
We have stood in the heaviness of the slave castles in Ghana, hiked the literally breath-taking Path of the Gods in Italy, danced samba through the vibrant streets of Brazil, broken fire-baked bread in the medinas of Marrakech, and wandered under the neon glow of Tokyo. I have watched them shop, joke, cry, flirt, affirm, and release. I have watched them remember themselves.
So if you ever see a group of Black women walking through a foreign city, dressed in bright caftans, laughing from their bellies, moving with presence and ease, know they aren’t just passing through. They are reclaiming space. They are rewriting stories. Black women aren’t just worthy of rest and celebration. They are experts at both when given the chance.
And if you see me nearby, smiling while carrying their suitcases, know that I am just thankful, and it’s definitely not because I want tips!
Dricks
