MAP
PHOTOS
VOICEOVER
FLIPBOOK
Prelude
After months of travelling through the Americas,
the lure of warmer weather and Caribbean horizons drew me south to Jamaica.
What followed was a remarkable 21-day cycling journey covering 724 kilometres
around an island famed for its reggae rhythms, vibrant culture, tropical
coastline, and warm-hearted people. From the beaches of Montego Bay and the
crystal-clear waters of Ocho Rios to the hills above Treasure Beach and the
laid-back communities scattered along the coast, every day brought new
encounters, unexpected kindness, and unforgettable scenery. Travelling at the
pace of a bicycle allowed me to experience Jamaica far beyond its tourist
façade—through its villages, history, cuisine, music, and the easy-going spirit
of its people.
Leaving the Americas – a Flight from Boston to
Montego Bay.
This was the
day I triumphantly fled the northern latitudes in search of warmer
weather—preferably the kind that doesn’t require three layers and a moral pep
talk. I packed everything into a single bag, feeling very smug and minimalist,
until Delta Airlines promptly punished me for it.
According to
their pricing philosophy, only one carry‑on bag was free; the first checked
bag cost $25, while the bike cost an additional $150! I stared at the
agent, wondering if the bike fee included a small share in the airline. It did
not. But at least they didn’t weigh the luggage, which felt like a tiny,
unexpected act of mercy.
The flight
itself was spectacular. The ocean below looked so clear you could practically
see disgruntled fish complaining about airline baggage fees. Tiny islands
drifted past like postcards someone had dropped into the sea. And then—Jamaica!
A sudden, glorious splash of green in the blue.
Immigration
insisted I buy an onward ticket before they’d let me in, presumably to ensure I
didn’t become a permanent beach ornament. So, I bought a ticket to Miami for
late November, hoping it would give me enough time to cycle through Jamaica and
Cuba. The United States, in its infinite creativity, had decided one could not
fly to and from Cuba, so I had to plan my escape routes like a Cold War spy.
Once
liberated, I collected my bag and bike, hailed a taxi to Gloriana’s, and opened
the bike box—only to discover the bike shop had disassembled the bicycle with
the enthusiasm of a toddler taking apart a toaster. I didn’t have the tools or
the knowledge to reassemble it, so I did what any sensible person would do:
panicked quietly, then went in search of a bicycle shop.
Montego Bay, Where I Nearly Acquired Dreadlocks
Early the
next morning, I marched my pile of bike parts to a shop, where a man reattached
the derailleur with the casual ease of someone buttering toast. Feeling
victorious, I went off to buy a swimsuit—because being in Jamaica without one
is like being in Italy without pasta: technically possible, but socially
unacceptable.
I also
visited a hairdresser, which nearly resulted in dreadlocks. The conversation
was entirely in Jamaican patois, and I understood none of it. To this day, I
have no idea whether they were discussing my hair, the weather, or the
geopolitical situation in the Caribbean.
The next
morning, I sat at a Hibiscus‑adorned table, savouring Blue Mountain coffee and
feeling like a million dollars. So good was it that I stayed an additional
day. This is how Jamaica works: you sit down for coffee, and suddenly you
discover you have lived there for three months.
Downtown
Montego Bay offered a smidgen of Jamaican history and a supermarket where I
stocked up on essentials. The history, however, was sobering. Jamaica’s past is
steeped in the brutal legacy of slavery. By the 18th century, Jamaica was
one of the most valuable British colonies… The life expectancy of an enslaved
West African in Jamaica was only seven years! It’s impossible to read this
without feeling both horrified and furious.
After
contemplating the Europeans’ astonishing capacity for cruelty, I wandered back
past beach bars where rum came in all colours, shapes, and sizes. I wasn’t in
the mood for rum, which is probably the least Jamaican sentence ever written.
Montego Bay to Fisherman’s Inn (42 km), Failing to
See Anything Glow
I set off
early, cycling out of Montego Bay in sweltering heat that made me question
every life choice leading up to this moment. Progress was slow because I kept
stopping at beachside bars—not for rum, but for water and conversation with
villagers, who were far more cheerful than the temperature warranted.
Falmouth
appeared, a typical Jamaican town with a long history and a few old buildings.
It was still too hot to explore, so I continued along the coast, melting
gently.
The village
of Rock is home to a phosphorescent lagoon, where one can see magical glowing
water at night. I checked into the Fisherman’s Inn, which was charming in the
way abandoned buildings in travel documentaries are charming. The room was
inexpensive, right on the lagoon, and had a lovely pool. The convenience store
at the gas station provided dinner, proving once again that gas stations are
the unsung heroes of travel.
I waited
eagerly for darkness, ready to witness the glowing lagoon. Then the rain began.
Not polite rain—biblical rain. The boat never went out. I was immensely sad
about the missed opportunity. I had come all this way to see glowing water,
and instead I saw glowing disappointment.
Diving the Crystal-clear Water of Jamaica - Fisherman’s
Inn to Ocho Rios (77 km)
True to my nature, I couldn’t wait another day and
pedalled off toward Ocho Rios, bravely entering what felt like the inside of a
malfunctioning oven. The heat was blistering, the hills were endless, and I
moved at the speed of a philosophical snail. But at least butterflies darted
around my head, not flies as in other parts of the world, which made me
feel like a Disney princess who had accidentally wandered into a Bikram yoga
class.
Past Runaway
Bay and Discovery Bay I cycled, where vendors sold jerk chicken accompanied by
rice and beans. The smell alone could make a vegetarian reconsider their life
choices. In Jamaica, stopping anywhere is an invitation for conversation.
Within minutes, I was offered a place to stay, a meal, and possibly marriage. I
politely declined and continued to Ocho Rios.
The Reggae
Hostel was perfectly located — a stone’s throw from the beach and right in the
town centre — and had the kind of laid‑back vibe where people came for one
night and stayed until their visas expired. I booked a dive for the next day,
because that’s what one does when surrounded by people who look permanently sun‑kissed
and spiritually hydrated.
The scuba
diving was extraordinary. The water was so clear it felt like swimming in a
giant bottle of Evian. Fish of every colour darted around, looking like they’d
been painted by an overenthusiastic art student. So fabulous was the dive
that I straightaway booked one for the next day because apparently I had
become someone who makes financially irresponsible decisions underwater.
Back at the
hostel, Sheldon and his girlfriend presented me with a bracelet in Jamaican
colours. It was such a sweet gesture that I momentarily forgot how sweaty I
was.
Jamaica, Where all women are Addressed Like a
Jamaican Princess - Ocho Rios to Port Maria (45 km).
I couldn’t
stay in Ocho Rios forever — although the hostel’s atmosphere suggested many had
tried — so I cycled along the coast. I didn’t get far before being flagged down
and offered accommodation. Jamaicans have the most charming way of addressing
people. You often hear: “Be careful, young lady” or “Hello, pretty girl, you
need a room?” even to an old hag like me. It’s not literal; it’s simply
their way of being warm and delightful.
The place I
stayed was rural but surprisingly modern, with stunning views and reggae
drifting through the air like a national fragrance. I watched Jamaicans roll
and smoke their joints, swaying gently to the rhythm. I love the Jamaican way —
slow to move but quick to smile.
Later, I
biked the three kilometres into Port Maria to pick up food, only to discover
the entire town already knew my whereabouts. A white woman on a bicycle is
apparently the Jamaican equivalent of a UFO sighting.
Port Maria to Port Antonio (78 km), on a Misbehaving
Bike
The route
swung inland over hills and past rural settlements untouched by the coast’s
tourist trade. Eventually, the path spat me out at a beach and then led toward
Port Antonio. My bike was having problems, so I looked for a shop — but it was
closed, and the town was a bit of a dump because roadworks had turned
everything into a muddy mess. I cycled through it, looking like a creature
recently excavated from a bog.
The next day,
the bike shop staff adjusted the gears as best they could, which is never a reassuring
phrase.
Despite being
in Jamaica for barely two weeks, I could easily see myself living there. The
scenery, the people, the food, the music — everything felt like a warm hug. I
wandered to the marina, savouring not just the occasional waft of marijuana but
the aromatic smoke from innumerable jerk stands. Jamaica is a place where even
the air feels seasoned.
Failing to Resemble Brooke Shields - Port Antonio
to Morant Bay (75 km)
Breakfast in
Jamaica is a hearty affair: saltfish and ackee, callaloo, yam, dumplings,
plantain — a meal clearly designed for people who do manual labour, not for
vegetarians on bicycles.
The road
hugged the coast for 40 kilometres before veering inland over hills toward
Morant Bay. Along the way, I passed the famous Blue Lagoon and stopped for a
dip. Sadly, I did not resemble the 14‑year‑old Brooke Shields in the movie. Instead,
I resembled the bedraggled 60-odd-year-old woman I was, who had cycled 75 kilometres
in tropical humidity. But the water was as crystal clear as portrayed in the
film, and that was consolation enough.
Morant Bay to Kingston, Home of Reggae Music (65
km)
Loading the
bike was leisurely, as the distance to Kingston was short. The day, however,
was another stinker, and the road deteriorated the closer I got to the city.
While slaving up one of the few nasty hills, a bee flew under my cap and stung
me on the eyelid. I yelped, swore, and briefly considered abandoning cycling
forever.
Once in
Kingston, I found the Reggae Hostel and was delighted to recognise travellers
I’d met in Ocho Rios. Jamaica is a small island, but apparently my social
circle was even smaller.
The next
morning, I woke with my eye swollen shut. A pharmacy gave me antihistamine
syrup, which made me sleepy, so I refrained from taking it again. Apart from
partying, there wasn’t much to do in Kingston, so I stayed one more day, doing
routine chores and discovering all there was to see in famous Kingston Town.
Kingston to Milk River Spa,“The Best Hotel in the
World” – Not (65 km)
I opted for
the seldom‑travelled coastal route, which turned out to be even more seldom‑travelled
than expected. The comments and looks I received indicated that not only was
this a less‑visited area, but a white woman on a bicycle was a rarity bordering
on myth.
Milk River, a
tiny community with a few churches and a large school, signalled the end of the
day’s ride. A sign indicated a hotel and spa — “The best hotel in the world”.
Judging by the condition of the signs, I didn’t expect much, but I investigated
anyway.
The hotel was
intriguing: private baths in an old wooden building, sparsely decorated rooms
along a creaky veranda, and water rumoured to cure numerous ailments. I wasted no
time submerging myself. The room rate included breakfast and dinner, which
thrilled me, as I was ravenous. Being the sole guest, I was treated like
royalty — albeit slightly sweaty royalty.
Milk River Spa to Junction - Meet Ghosts, and
Ignore Sensible Advice (65 km)
Before
departing, I had one final dip in the hot spring — partly for nostalgia, partly
because I suspected it might be the last warm water I encountered for a while.
Then I followed the coastal path west, pedalling past God’s Well, a deep sinkhole
rumoured to be inhabited by the ghosts of a Taino maiden and a scuba diver who
drowned there while trying to establish the depth. Jamaica is full of stories
like this: tragic, mysterious, and delivered with such casual cheer that you
begin to suspect the ghosts are considered part of the local tourism economy.
A short while
later, I stopped at Alligator Pond for lunch. Little Ochi was a popular
restaurant where one could order freshly caught fish on the beach. The tables
sat in brightly painted boats on stilts, reggae blaring from a rickety timber
bar. It felt like dining inside a cheerful hallucination.
Following
lunch, I set off up the mountain in the stinking midday heat. The climb was
steep, the road was in poor condition, and my enthusiasm evaporated somewhere
around the second switchback. People called me in to rest and advised me to
take a taxi, insisting Treasure Beach wasn’t reachable by bicycle. I very
nearly believed them — the going was dreadfully slow and exhausting — but stubbornness
is a powerful motivator. Upon slinking into Junction, I spotted a guesthouse
and called it a day. It was cheap but comfortable, and I was profoundly
grateful for the pool in the oppressive heat.
Junction to Treasure Beach - There Is No Such Thing
as “Cool Morning Air” (30 km)
I emerged at
first light to tackle the remainder of the climb in what I naively hoped would
be cooler morning air. Unfortunately, I soon discovered there was no such thing
as “cooler morning air”, as the weather was already sweltering. There were days
I doubted my sanity, and this was one of them.
Villagers
again informed me that Treasure Beach was unreachable by bicycle, which made me
wonder whether Treasure Beach was actually a metaphor. Fortunately, only one
hill remained, and I descended to the coast.
The landscape
was surprisingly dry and barren, looking distinctly African, with thorn trees
and goats roaming about. Treasure Beach itself was refreshingly un‑resort‑like:
a few beachside restaurants, a handful of guesthouses, no lounge chairs, just
fishing boats and shade. I found a place on the beach and kicked back for the
remainder of the day, feeling like a lizard on a warm rock.
Treasure Beach to Black River- In search of Crocodiles
(30 km)
A short cycle
brought me to Black River, where I bunked down at Waterloo Guesthouse, built in
1819 and reputed to be the first place in Jamaica to have electricity. The town
was tiny but interesting, with a smidgen of promenade and a few old wooden
buildings dating back to Jamaica’s early days.
I overnighted
in Black River to take a boat up the river and into the Great Morass — a swampy
wonderland featuring plenty of birdlife and a fair share of crocodiles. It was
the kind of excursion where you spend half the time admiring nature and the
other half calculating how fast you could paddle if the crocodiles suddenly
developed ambitions.
Black River to Negril, - Jamaica’s Party Town (75
km)
The following
day, I continued along the coast to Negril, Jamaica’s party town, where
everything was overpriced and immensely touristy. Still, the Caribbean Sea’s
crystal‑clear water lured me in, and I spent the remainder of the day floating
like a blissful piece of driftwood.
Negril is
also the epicentre of Jamaica’s “rent‑a‑dread” phenomenon. It’s not unusual in
Jamaica to see middle‑aged ladies strolling hand in hand with a handsome young
stud. Countless European women maintain ongoing relationships and return
regularly, much like older European men who frequent Thailand. Jamaica, it
seems, is a place where romance is available in convenient seasonal packages.
Negril to Montego Bay - A Downpour and a Visit to a
200‑Year‑Old Waterwheel (75 km)
My last day
of cycling offered an easy and interesting ride to Montego Bay. The road hugged
the coast, and I got caught in a heavy downpour — not bad, considering October
is one of Jamaica’s wettest months. Curio sellers called me in to take shelter,
and I wasted no time accepting their generosity.
Once the rain
abated, I investigated the nearby Tryall waterwheel, approximately 200 years
old and still turning. It looked like the sort of thing that should be in a
museum, yet there it was, casually spinning away as if it had never heard of
retirement.
Back in
Montego Bay, I returned to Gloriana’s, the best‑priced abode I could find. My
flight to Cuba was a week away, leaving me plenty of time to explore.
Montego Bay, Avoiding Cruise‑Ship Prices, and Building
a Bike Box Out of Fridge Packaging
Jamaica’s
temperatures scarcely change from one day to the next, hovering around 25–30°C
year‑round. In October, clouds gather in the evenings, followed by
thunderstorms that never last more than an hour or two — all with virtually no
change in temperature. Jamaica is meteorologically consistent, like a country
that has decided weather variation is unnecessary.
With time to
spare, I visited a nursery offering colourful and exotic plants. Jamaica’s
tropical climate facilitates a diverse ecosystem, though much of the original
forest was cut down after the Spanish arrived in 1494. Thankfully, a few
indigenous plants survived the European enthusiasm for clearing things.
I wandered
the streets of Mobay, packed with curio stalls selling similar items. Prices
almost doubled on cruise‑ship days, so shopping required strategic timing.
Meanwhile, I searched for a bike box but couldn’t find any. In the end, I stuck
two fridge boxes together, hoping they wouldn’t fall apart before arriving in
Cuba. It looked like a cardboard Frankenstein, held together with optimism and
duct tape.
The Long Way to Cuba
The most
economical flight to Havana was via Panama — a 2000‑kilometre detour to reach a
destination barely 400 kilometres away. Travel logic is a mysterious thing.
The taxi ride
to the airport was short, and mercifully, the airport had a wrapping service,
as I doubted my homemade bike box would last. It looked like something a child
might build for a school project titled “Transportation in the Modern World.”
From the
start, Cuba felt different. The plane had an abundance of space — a rarity
today — and one could even snooze before descending. We witnessed an unusual
sunset revealing well‑organised farmlands below, likely tobacco fields.
Clearing
customs was exceptionally easy. Then, with formalities done, I excitedly hailed
a taxi to Hostal Peregrino in Centro Havana. When I rang the bell, a key
tied to a string was lowered from the window above. It was a wonderfully
theatrical welcome, marking the start of a remarkable visit to the fascinating
island of Cuba.
Epilogue
Jamaica left a far deeper impression on me than I
had expected. The island’s breathtaking landscapes, infectious music, colourful
culture, and exceptionally friendly people combined to create one of the most
enjoyable chapters of my travels. Whether sharing conversations with villagers,
cooling off in the Caribbean Sea, exploring historic towns, or struggling up
steep hills in the tropical heat, every experience added to my appreciation of
this unique country.
By the time I returned to Montego Bay, my bicycle
and I had completed a memorable circuit of the island, rich in adventure and
human connection. Jamaica was a place where strangers became friends, where
life moved to the rhythm of reggae, and where a smile was never far away. As I
packed my bike into a makeshift box and boarded a flight bound for Cuba, I
carried with me not only memories of 724 kilometres on the road, but also a
lasting affection for an island that had welcomed me with open arms.
