The ferry from Guadeloupe cut through a sea the colour of absinthe. I was on my way to Dominica, an island that few first-time Caribbean visitors think of, and my feet were stuffed into a brand-new pair of Sperry boat shoes — the giveaway prize that had landed me here in the first place. The contest promised “a Caribbean adventure,” and the shoes arrived before the itinerary did. I remember unboxing them on my apartment floor, thinking about how travel brands often sell you a feeling before you even step out the door. What I didn’t expect was how much that specific pair of canvas-and-rubber would shape the way I moved through the next ten days.
Let me be clear: this is not a product review. I’m not here to tell you that you must buy Sperry shoes to travel well. What I want to share is the texture of a trip that started as a sweepstakes entry — a moment of digital luck — and turned into one of my most grounded solo journeys. The giveaway was hosted by Sperry in 2017, and it paid for the flight, accommodation, and a loose set of experiences on the island of Dominica. I brought nothing else but a 40-litre backpack and a willingness to move slowly. For a solo woman, that combination — light luggage, water-friendly footwear, and a destination that rewards patience — turned out to be unexpectedly freeing.
Why Dominica Instead of the Typical Beach Holiday
Most Caribbean advertisements show white sand and cocktails with umbrellas. Dominica offers none of that if you stay inland. The island is volcanic, rainforest-draped, and crisscrossed by rivers that smell like wet earth and wild mint. The giveaway itinerary included a guided hike to the Boiling Lake, snorkelling in Champagne Reef, and a stay at a small eco-lodge near the Morne Trois Pitons National Park. None of these required high-end gear. But they did require a shoe that could walk on wet volcanic rock, wade through warm shallows, and dry out overnight. The Sperry Top-Siders I wore were originally designed for sailing — they gripped wet decks — and that grip translated surprisingly well to slick boulders and coral rubble.
I mention the shoes only because they became a quiet part of my routine: slip them on, step out of the cabin, walk to the river. No sandals flapping, no boots too heavy. For a solo traveller who prefers not to check a bag, a single pair of all-purpose footwear that works on a hiking trail and at a roadside fish fry is a small kind of genius. I’ve used the same principle since, whether tramping through the coves of Kefalonia in a different brand or wandering Lisbon’s cobblestones. The lesson is not about the brand; it is about choosing one versatile item that lets you stop thinking about your feet and start noticing the world.
The Giveaway That Turned Into a Real Solo Routine
For a solo woman, arriving in a new country with a sponsored itinerary can feel strange — there’s a curated quality that removes some of the scrappiness of independent travel. But I learned to treat it as a skeleton, not a cage. Every morning I woke up at the eco-lodge before the guides arrived and went for my own walk along the coast. The breakfast was always fresh papaya and saltfish, and the staff treated me like a regular after the second day. That routine — tea at sunrise, a quiet stretch, a walk in the same boat shoes that had arrived in the mail — grounded me in a way that pure spontaneity sometimes doesn’t. As someone who has written about the balance between structure and freedom in solo travel before (I explored this idea in a post about the digital nomad life a few years back), I recognised that the giveaway’s schedule was only a starting point.
One afternoon I skipped the planned excursion to the Emerald Pool and instead took the local bus to Portsmouth, a town on the northwest coast. I sat in a small rum shop, shared a plate of fried plantains with a woman who ran a guesthouse, and listened to the rain drum on a corrugated roof. That memory — not the formal hike — became the emotional centre of the trip. The giveaway gave me the flight; the island gave me the real adventure.
What the Caribbean Adventure Taught Me About Packing for Solitude
I kept a small notebook during that trip, and looking back at it, most entries are not about the shoes or the contest. They are about the quiet moments: the sulphur smell of the volcanic vents at sunrise, the way the sea glowed blue-green at Champagne Reef, the taste of roasted breadfruit from a roadside stand. The giveaway was a door, but the experience itself was unsponsored. Here are a few practical things I carried away that you can use whether or not you ever enter a contest:
- Choose a single base island, not a multi-stop cruise. Dominica is small enough to explore by rented car or public transport. Staying in one eco-lodge let me build a routine and relationships. For solo women, a familiar base reduces decision fatigue.
- Waterproof footwear is worth the weight. Even if you don’t hike, Caribbean islands are damp. A shoe that dries quickly and doesn’t slip on wet docks or boat decks will save you from blisters and lost hours. My Sperry shoes did that, but any sturdy boat shoe or water sandal with a rubber sole works.
- Talk to local women. The women who run market stalls in Roseau have the best advice — where to eat, which beaches are quiet on a Sunday, how to avoid the tourist traps. I learned more from three conversations than from any guidebook.
- Pack a sarong or a light wrap. It serves as a towel, a picnic blanket, a scarf for church visits, and a cover-up for volcanic hot springs. I used mine every single day.
From Giveaway to Genuine Slow Travel
The phrase “slow travel” gets thrown around a lot, but on Dominica it is not a choice — it is a necessity. The roads are winding, the internet is patchy, and the island does not cater to the visitor who wants to tick boxes. The giveaway had planned one major activity per day, which left the afternoons empty. That emptiness became the real gift. I spent hours reading on a hammock, watching frigate birds circle the bay. I took a cooking class with a local family and learned to season fresh fish with green banana and coconut milk. I wrote postcards to friends, something I hadn’t done in years.
For a solo woman, a trip that is half-curated and half-open can be a perfect middle ground. You get the safety net of a confirmed itinerary and the freedom to wander on your own terms. The giveaway had no rules about where I ate dinner or what I did in the evenings. I used that margin to explore the village near the lodge, buy handmade vanilla from a farmer, and watch a cricket match at a school field. I never felt unsafe. Dominica is not a high-crime destination for tourists, and the hospitality is genuine.
One Final Detail: The Shoes Held Up
I still have those Sperry shoes. The canvas is faded, the rubber sole is worn smooth on the heel, but they became my primary travel footwear for years after that trip. They have walked through mud in the Amazon, along the stony paths of Cinque Terre, and through puddles in Berlin. The giveaway was a one-time event — a contest that a friend told me about on Facebook — but the real Caribbean adventure was the permission it gave me to trust a single piece of gear and an island that didn’t perform for tourists. If you ever get the chance to enter a similar contest, do it. But more importantly, take the spirit of that adventure — light, slow, curious — and apply it to whatever trip you plan next, even if you buy your own shoes.
