Let’s be honest. Setting your alarm for a 4 a.m. run in the freezing, dark, slushy misery of winter is… a special kind of self-punishment. Your running shoes are stiff, your lungs hurt, and you’re pretty sure that car just splashed you on purpose.
But what if 26.2 miles didn’t have to be miserable? What if, instead of dodging black ice, you were dodging a stray coconut? What if your post-run recovery drink was a rum punch (consumed responsibly, of course)?
Welcome to the world of marathons in the Caribbean.
This isn’t just about running; it’s about the “run-cation.” It’s a chance to trade your concrete jungle for a real one, to have your sweat immediately dried by a warm trade wind, and to cross a finish line that’s probably just steps from a turquoise ocean. These races combine serious athletic achievement with an unbeatable vacation vibe.
We’ve rounded up the top 10 marathons in the Caribbean that will have you lacing up your shoes and booking a flight, faster than you can say “Pace-setting steel drum band.”
When: Early December Why We Love It: This is, without a doubt, the most soulful marathon on the planet. The Reggae Marathon is less of a race and more of a 26.2-mile party. You’ll find live reggae music pumping at every single mile, and the “go-slow” Jamaican vibe is infectious. The race starts in the dark at 5:15 a.m. with tiki torches lighting the way. The Course: It’s flat, fast, and an out-and-back route along Negril’s famous Seven Mile Beach. Best For: First-timers, music lovers, and anyone who wants a Bob Marley finisher trophy.
When: Mid-January Why We Love It: If you’re looking for a world-class race with stunning scenery, this is it. Marathon Bahamas is an AIMS-certified, professional event that just happens to be in paradise. It starts at Junkanoo Beach (yes, on the oceanfront) and runs through the historic downtown of Nassau. The Course: Mostly flat, with the main “challenge” being two bridge crossings—one from Nassau to the beautiful Paradise Island and back. The views are 100% worth the climb. Best For: PB-chasers who want a view, and runners seeking a big-event feel.
When: Early December Why We Love It: This is one of the oldest and most beloved marathons in the Caribbean. Celebrating over 40 years, the Run Barbados weekend is a true running festival. It’s not just the marathon; there’s a 10K, half-marathon, 5K, and even a “Glow” fun mile. The Bajan hospitality is legendary, and the post-race beach party at Carlisle Bay is the perfect reward. The Course: A scenic, relatively flat route that takes you along the stunning coastline. Best For: The whole family, history buffs, and runners who love a festive race weekend.
When: Early December Why We Love It: This race has a “boutique” feel. It’s small, incredibly friendly, and flawlessly organized. The 5 a.m. start time means you’ll be running as the sun rises over the Caribbean—a truly magical experience. Plus, the water stops are legendary, often themed and staffed by the most enthusiastic volunteers you’ll ever meet. The Course: A flat and fast two-loop course that runs along the waterfront and through the residential areas of South Sound. Best For: Early risers, PB-chasers, and those looking for a personal, welcoming race.
When: Late November Why We Love It: Where else can you run through a UNESCO World Heritage site and across one of the world’s most famous floating bridges? The course takes you through the postcard-perfect, colorful Dutch colonial buildings of Willemstad. The highlight is crossing the “Swinging Old Lady,” the Queen Emma Pontoon Bridge. The Course: A unique road-trip of an island, combining city streets, coastal roads, and that iconic bridge. Best For: Culture vultures, architecture lovers, and Instagram runners.
When: Mid-January Why We Love It: Okay, okay. We know. Bermuda is technically in the Atlantic. But it’s part of the legendary “Five Island Challenge” (along with Jamaica, Barbados, Cayman, and Bahamas), so it absolutely makes the list for its Caribbean spirit. This isn’t just one race; it’s for the glorious overachiever. You can run a mile on Friday, a 10K on Saturday, and then the full marathon on Sunday. The Course: A challenging, hilly loop with breathtaking coastal views that will make you forget your legs are screaming. Best For: The beautifully insane runner who thinks 26.2 miles isn’t quite enough.
When: Mid-November Why We Love It: This is more than a race; it’s a trip back in time. Running through Havana is an experience like no other. The course starts and finishes at the Paseo del Prado and takes you past iconic landmarks like the Malecón, Revolution Square, and Old Havana. The energy is electric, with locals cheering you on the entire way. The Course: A two-loop course that is mostly flat, but the Cuban heat can be a challenge. Best For: The historian, the adventurer, and the runner who wants a truly unique medal.
When: September Why We Love It: This one is not for the faint of heart. While the island is a tiny, tranquil paradise, the marathon is a beast. The race loops the entire island, taking you through lush rainforests, past historic sugar plantations, and up… “The Anaconda.” The Course: It’s hilly. No, really. The famous “Anaconda Hill” at mile 23 is a 2.5-mile climb that will test your soul. But the bragging rights are forever. Best For: The hill-lover (you weirdo), the challenge-seeker, and those who want to earn their post-race beer.
When: April Why We Love It: If your ideal “run-cation” involves an all-inclusive resort, this is your race. This marathon is designed for the running tourist. It’s a fast, flat course that starts and ends at the Punta Cana Resort & Club, taking you through pristine golf courses and coastal roads. The Course: Very flat and very fast. It’s a certified Boston Qualifier, making it a perfect destination race to punch your ticket to Boston. Best For: The BQ-chaser who wants a piña colada at the finish line.
When: January Why We Love It: As one of the longest-running marathons in the region, this race is pure, unadulterated Trinidadian culture. It runs from the center of the island to the capital, Port of Spain. The timing in January means you’ll feel the “pre-Carnival” buzz in the air, with soca music and a party atmosphere. The Course: A point-to-point race that offers a diverse look at the island’s suburbs and city. Best For: The runner who wants to feel the local pulse and maybe stay for Carnival.
Absolutely! Races like the Reggae Marathon and Cayman Islands Marathon are particularly good for first-timers. They are exceptionally flat, have incredible crowd and volunteer support, and the “party” vibe helps take the pressure off.
Generally, no. Almost all of these marathons have open registration and are welcoming to runners of all abilities, from elite athletes to first-time walkers. The only exception would be if you’re trying to get an elite BQ spot, but for general entry, just sign up!
It’s definitely warm! But race organizers are smart. Almost all marathons in the Caribbean have a very early start time—we’re talking 3:00 a.m. to 5:30 a.m. This ensures you run most of the race in the dark or in the cool pre-dawn hours, beating the worst of the sun. Hydration is still absolutely key!
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