Fun-loving Jost van Dyke has been catering to the yachting community for decades. This small, under-the-radar hideaway is full of pristine beaches and buzzing seaside bars. The Soggy Dollar is perhaps the most famous, where talented bartenders sling rum-spiked Painkiller cocktails infused with cream of coconut and Grenadian nutmeg. Spend some time wandering around White Bay, with its beautiful stretch of shore lined with restaurants. Nearby, you can unwind in the locally loved “bubbly pool,” a natural rock formation that fills with bubbles as waves crash around it.