Windward Point
Anguilla's wild, windswept eastern edge
Why Go
At the far eastern tip of Anguilla, the manicured resort island falls away and something rawer takes over ΓÇö a rugged headland where Atlantic surf pounds sharp limestone, cacti guard the trail, and pelicans wheel overhead against a 360┬░ panorama of Scrub Island, St. Martin, and St. Barths.
The Experience
Windward Point is the anti-Anguilla: no beach bars, no loungers, no rum punch runners. Just an undeveloped ribbon of coastline at the island's easternmost extreme, reached by a roughly 2.5-mile loop trail out of Island Harbour that most walkers knock out in under an hour. The path threads across a moon-like plateau studded with Melocactus and low scrub, then climbs to a modest summit where the wind hits hard and the view opens onto open ocean and neighboring islands. A working lighthouse anchors the point, and pocket coves below hide tidepools and dramatic rock arches carved by relentless swell. It's the kind of place where you'll go an hour without seeing another soul.
What to Try
Hike the full loop counterclockwise so you finish along the coast with the wind at your back. Climb to the top of the hill for the panoramic view of Scrub Island, St. Martin, and St. Barths (bring binoculars). Scramble down to the rocky shoreline to watch the Atlantic explode against the cliffs ΓÇö but stay well back from the edge, the swell is unpredictable. Time the walk for late afternoon and stay for sunset over the interior of the island.
Insider Tip
Wear real sneakers, not flip-flops ΓÇö the trail is peppered with cacti and razor-edged limestone that will shred sandals in minutes. Start with a full water bottle and a hat; there is zero shade and no facilities of any kind once you leave Island Harbour. Cell signal is spotty, so download an offline trail map before you set out.
The Practical Stuff
Location: Eastern tip of Anguilla, trailhead accessed from Island Harbour. Distance: ~2.5-mile loop, ~53 minutes at an easy pace. Difficulty: Easy to moderate, mostly flat with one short climb; uneven, rocky footing throughout. Cost: Free, no permits or guides required. Best time: Early morning or late afternoon to dodge midday heat; avoid after heavy rain when rocks get slick. What to bring: Sturdy closed-toe shoes, sun protection, at least 1L of water per person, camera. Not suitable for young kids or anyone with mobility issues due to loose rock and cacti.
Pair It With
- Island Harbour — The nearest fishing village and natural start/end point for the hike ΓÇö grab a fresh grilled lobster lunch or a cold Carib at a beachside shack before or after your walk.
- Scilly Cay Guide — A short boat hop from Island Harbour lands you on this legendary sandbar for rum punch and grilled crayfish ΓÇö the perfect reward after a sweaty Windward Point loop.
- Shoal Bay East — After roughing it on the point, decompress on Anguilla's most famous stretch of powder-white sand and turquoise shallows, about a 15-minute drive west.
- Heritage Collection Museum — A tiny, personal museum in East End that adds context to the wild landscape you just walked ΓÇö Anguilla's salt-pond, seafaring, and colonial history in one visit.