Returning To Tobago Taught Me How To Travel Alone Without Feeling Lost

“Tobagonians are resilient people,” Marsha Patrick, our friendly yet firm host, repeatedly tells us on our journey around the island. The 7.5-mile-wide, untouched land changed hands 33 times during colonialism, ping-ponging between the French, Dutch, Spanish, British, and even the Courlanders (modern-day Latvia). Despite a legacy rife with colonial conflict, slavery, and bloody uprisings, there is something distinctly peaceful about the people and island of Tobago. Much like the land they tend, their spirit is rich, and their pride is unshakeable. They are not boastful; they express passion for their heritage and home.

Even though they form a country with Trinidad, the two islands have strong identities and cultural differences that reveal the breadth of the population. Tobagonians are quick to remind you that Trinidad needs them for their rich soil and oil-rich waters. They’re not just the little sister to Trinidad but a force of their own, central to strengthening Trinidad’s metropolitan centre in Port of Spain.

I first visited Tobago exactly 10 years ago as an angsty 19-year-old wanting to try some solo exploring and break free from the watchful eye of my aunt, a strict follower of the Ethiopian Orthodox Tewahedo Church. She is a small, soft woman with pro-Black politics and images of Haile Selassie scattered around her large countryside home perched at the edge of a mountain in the northwest of Port of Spain. I left her house on the ferry seeking adventure, but the slow-moving island felt incongruent with this overflowing desire for thrill.

I struggled to navigate it independently, without a car, and had no connections to lean on. Feeling defeated and broke from expensive taxis, I returned to Trinidad, where my aunt warmly greeted me, knowing it was a tall order to make the trip alone. I was frustrated with myself. I thought solo travel was meant to be fun and enriching, but why couldn’t I get it right? I knew this island was special and the people were friendly, but I was inexperienced and unprepared for what Tobago had to teach me.

When the opportunity to return 10 years later for the Heritage Festival and Emancipation Day celebrations presented itself, I knew I had to take it. At 29, I had solo-travelled many times, was confident in myself, and returned to Tobago searching for something more profound: a feeling of belonging.

One of the early ventures on this rediscovery trip was Sunday Harvest in Speyside village. It was a transformative experience. Picture this: you’re hosting a BBQ for your family, but also for the entire street. Every third house hosts a BBQ; you can pop into those homes, too. People from two villages over drop by to eat food, listen to music, and drink at the makeshift free bars erected on terraces and driveways. Sunday Harvest, a regular occurrence across the island, was community in a way the British mind could not comprehend.

I host events for Strangers in London, where we encourage people to attend solo. For a long time, I thought of what I did as novel, but this is simply a way of life in the Caribbean. I felt shy walking into people’s homes, convinced I was being intrusive, but their warm smiles dissolved my hesitation. It took me a while to reconcile that I was a stranger to these people, yet they embraced me as if I were one of their own. Selflessness like that is rare in the UK, where “island of strangers” is the fearmongering rhetoric our Prime Minister uses to discuss diversity.

Travelling back to the Caribbean gave me a sense of purpose and shifted my politics from rage to compassion. Seeing William Trim, the retired Head of the Tobago Forestry Division, still hosting tours at the Main Ridge Forest Reserve, speak so passionately about the ecosystem he dedicated his life to preserving, made me conscious of how my actions impact this land. When we followed Newton George up a steep hill on Little Tobago Island and he pointed out the birds soaring above with childlike wonder, I became attuned to the birdsong around me. When I see birds flying around my aunt’s avocado tree, I think of Newton’s father, once the sole tenant of Little Tobago, caring for the land and passing his knowledge down to his son. I’ve never felt so connected to the earth as I did while watching people who look like me tirelessly marvel at their homes.

One of the last stops on our journey through the island was Fort King George. We paused outside a crumbling brick building marked “Punishment Cells.” As beautiful as the area was, something about it felt unsettling. Standing outside the hollow structure, our guide recounted its dark history: enslaved people were shipped over, guided through a now-boarded-up tunnel, and imprisoned. Packed in tight confines, they were forced to break down large stones to build the prison that held them captive. Each time I think I’ve heard the worst story about slavery, I am proved wrong. That story stayed with me as I departed Tobago and helped to frame the next part of my trip.

After a week of discovery in Tobago, I landed in Trinidad. I was greeted by my smiling cousin — we used to call him Irie Nyrie and Rasta Mouse because of his long dreads, now cut into a sharp shoulder-length bob. It was August 1st, Emancipation Day, an incredibly significant celebration across the Caribbean that marks the abolition of slavery. Each island has its own traditions. An hour away in Barbados, people participate in the annual Emancipation Day walk. In Jamaica, Redemption Fest comes alive at Emancipation Park. In Trinidad, festivities begin at 4 a.m. with a libation ceremony - liquids poured in the streets as an offering to the ancestors - and end at 7 p.m. with a Flambeau Procession from Queen’s Park Savannah to the famous All Stars Pan Yard.

As we drove to the Emancipation Village, the sound of African drumming pulsed through the air, and crowds in vibrant West African-inspired prints filled the streets. Like me, you could feel their yearning for a connection to a past unblighted by slavery - something bigger than the islands where they found themselves. They carried the weight of a gruesome history but were fuelled not by despair, but by hope and an unrelenting desire to reclaim their history and rewrite their future.

My history, as someone from the Caribbean, is one of violence, enslavement, and colonialism. Being born and raised in the UK, it is also one of anti-Black racism and classism. Somewhere in that injustice, I lost faith that things could improve. I forgot that those before me fought for their freedom and won.

Travel is often framed as an escape; a way to briefly step into a life that isn’t your own. I don’t want to escape my life anymore. When I travel — especially to the Caribbean — it’s about grounding myself more deeply in who I am and where I come from. Because of this, I’m prioritising being with and around other Black people.

I returned to the UK just in time for Notting Hill Carnival, where I play mas with friends and celebrated a huge London event rooted in the same rich islands I just left. To me, this is the marker of a successful trip; one that enriches my life rather than convincing me I need to run away from it.