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Site · #185 of the Top 500

Grand Cayman

Cayman Islands

A low coral island about 35 km end to end, with a small harbour capital on the west coast, a famous beach running north from it, and a far end an hour's drive away through villages that once rowed out to save the wrecked. Every beach here is public by law, so the crowds gather at Seven Mile Beach and George Town while the East End parks, the north-coast bays and the old capital at Bodden Town stay quiet. A rental car reaches all of it; the loop round the island is roughly 110 km.

5 challenges · 29 stops

Harbour Wall to Smith's Cove crestSTARTER

Harbour Wall to Smith's Cove

≈ 4,000 steps1.8 mi · about 2 hoursStarter · 3 stops · 500 credStart where you live.

Three stops on foot from the harbour fort to a swimming cove: about two and a half kilometres along the waterfront road, two hours with a swim at the end, and nothing to pay anywhere. Best on a morning with no cruise ships in the bay.

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Coves and Cannons crestSTANDARD

Coves and Cannons

17 mi by carabout 5 hoursStandard · 5 stops · 600 credOne trip earns it.

The south coast over half a day with a car, west to east: a seafront park, the turtle beach at Spotts, the cannons and the public beach of the old capital at Bodden Town, and a National Trust beach at Breakers. Five free places to stand, about 30 km of driving one way.

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Hell and Back crestSTANDARD

Hell and Back

≈ 5,000 steps + 7.0 mi by car2.4 mi on foot · about 4 hoursStandard · 5 stops · 600 credOne trip earns it.

Five stops in West Bay over half a day with a car: the black rock at Hell, the empty beach at Barkers, then three public beaches down the top of Seven Mile. Bring swimsuits and a picnic; every stop is free, and Barkers closes at dusk so take it before the beaches.

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Round the Island in a Day crestADVANCED

Round the Island in a Day

≈ 9,000 steps + 50 mi by car4.4 mi on foot · a full dayAdvanced · 8 stops · 800 credGetting there is not the hard part.

Eight stops in one long day with a car, clockwise round the island: a forest trailhead, the blowholes and the two East End parks, the far beach at Colliers, then Rum Point and Starfish Point on the north coast, and a free tower at Camana Bay for the last light. Roughly 110 km of driving; leave early and pack lunch.

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The Quiet Ones, Over Two Days crestADVANCED

The Quiet Ones, Over Two Days

38 mi by cara full dayAdvanced II · 8 stops · 800 credGetting there is not the hard part.

Eight places the day-trippers miss, spread the length of the island and best taken as two outings: a morning in West Bay and George Town and an afternoon in Bodden Town, then a second day on the north coast from Old Man Bay to Cayman Kai by way of the Queen's Highway. About 150 km of driving in all, and not one ticket.

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Counted between stops; you'll walk more at each one.

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