Roadtrip Jamaica: Cool Spots and Stops | Negril to Ocho Rios

“Whooaaa waaaiiiiit, what was that??”


I can’t recall how many times we turned around during our road trip. Or how often we gasped. The “oohs” and “aahs” common to first-time visitors to Jamaica. Except, it’s not our first time, and we’re not typical tourists. We’ve both lived in Jamaica for months at a time – six months here, four months there, year after year. We know the land, the people, the culture, and yet we still gush. Three years of “shooting” this island so far for me. But I have more to cover, much much more. I still dream of all the roads I have yet to explore and show, new ways to immerse myself and capture the essence of this island.

We are just barely an hour away from Negril when we start making U-turns and photo stops. The plan was to drive to Ocho Rios on Day 1 and arrive there around 2 p.m. so we could look for a place to stay for the night, before nightfall. A sort of pit stop on our way east of the island to Port Antonio, Long Bay, Manchineal and ultimately Kingston.

Well, we didn’t make it to Ochie until 8 p.m. on the first day. That’s the thing in Jamaica, there’s always something going on on the road – someone fishing, some cute hut perched on a cliff calling your name, a fresh fruit stand to sample, an unexpected river to swim in or a friendly Jamaican to share stories with. Or even familiar faces to meet up with halfway up the island, because you never know who’s on the road too that day. There’s no rush, everything will happen when it will, if you will.

No matter how often you’ve traveled a road, there’s always something you missed before, or maybe even something new to absorb. And with a rental car, you can go wherever you please. No driver to wait on you (that always made me uncomfortable), no structured or forced stops, and no limits to off-the-beaten track drives. Just endless vistas and “cool spots” along the way.

(Above)  View of Montego Bay, about an hour and twenty minutes from Negril.

(Above & Below) Cool Spot Bar & Grill – Falmouth

Runaway Bay, Flavours Beach

(Above & Below) Flavours Beach Bar & Restaurant | Runaway Bay

Lebawit Lily Girma

Lebawit Lily Girma is an award-winning travel journalist, photographer, and guidebook author specializing in the Caribbean region. Her work has been published in major travel publications, including CNN, AFAR, Delta Sky, Lonely Planet, Shermans Travel, and BBC, among others. A self-professed "culture-holic," Lily left her native Ethiopia at age one, fast developing a passion for the expat Caribbean life. In 2008, she ditched her US corporate law career for the road and created Sunshine and Stilettos—a travel photography blog showcasing authentic ways to experience the Caribbean, through culture and nature. Lily has since partnered with Caribbean tourism boards and travel brands on major content projects. She also authors print guidebooks on three destinations, including Belize, the Dominican Republic, and Jamaica. Read more on her site,

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