Nevis Mt. Nevis
This sombrero-shaped island (pictured) is named for the snow-like clouds capping its 3,232-foot peak, which, unfortunately, impinge the view about half the time. Hike it anyway the muddy slog, which requires affixed ropes in places, will earn you plenty of bragging rights (and sore muscles). Guides available through www.nevisnaturetours.com.
Curaçao Mt. Christoffel
Dont be fooled by the first half of this hike: The easy grade spikes into a true boulder scramble to Christoffels 1,240-foot peak. At the top, a stunning vista sometimes all the way to Venezuela makes the effort worth it. Mt. Christoffel National Park is about a 45-minute drive from the capital of Willemstad, but mere minutes from the nearest hotel, the Lodge Kura Hulanda. You can start your hike from the parks Visitor Center and walk about 30 minutes to the trail head, but just parking near the trail head is a better bet. Start early: The sun-baked route gets hot fast, even with a breeze.
Dominican Republic Pico Duarte
At approximately 10,000 feet, Pico Duarte is the Caribbeans highest peak but not necessarily the most difficult, depending on the route. All climbs require a guide and at least two days; the most scenic is goes through Valle de Tetero, with waterfalls and petroglyphs along the way. Guides are required, and hiring a tour operator (www.iguanamama.com or www.grupobaiguate.com) is recommended.
St. Lucia The Pitons
Take your pick of the Pitons Petit or Gros a UNESCO World Heritage site for its lush landscape and diverse animal and plant life. Petit (2,461 feet) is steeper; its not a government-sanctioned climb but some experienced hikers attempt it anyway. Gros Piton (2,619) is almost as challenging; roots, trees and steps cut into the upper section provide welcome aid through the hellish half-mile to the top. Start early to avoid descending in the dark; guides are available through most hotels or at www.heritagetoursstlucia.org.