This Eastern Caribbean island might be meager in diameter, but its staggering terrain is diverse enough to span countries 10 times its size. Think volcanic beaches set against sparkling seas, a densely packed rainforest harboring waterfalls and jagged cliffs, and a sprinkling of charming fishing villages along the coast. The weather is glorious in the Winter, and although the island is revered for its ultra-luxurious resort scene, you can also score ocean-adjacent accommodations on Airbnb for well under $100 per night.