Sweet Spot: Ivan's Stress Free Bar

Island: Jost Van Dyke

Imagine a front-porch hootenanny on a slice of sand and you'll have happy hour at Ivan's. Run by seventh-generation Jost Van Dyke resident Ivan Chinnery, this beachfront empire consists of an open-air shack, a few cabins, and some tents. What the place lacks in creature comforts, it makes up for in conviviality: If you're lucky, you may find crack guitarist Ivan playing along with visiting talent like, say, Keith Richards. Build courage to add to the melee with the house rum punch (it includes guava) and an order of shrimp sautéed in lemon-garlic butter. And no worries: If the festivities run too late for you to water taxi it back to your boat, there's always a tent, a cabin, or a hammock to curl up on.

Name of beach: White Bay

Meal Ticket: Entrées, $18–$40

Vibe: Sandy campfire sing-along

Best Day: Thursday, for the weekly barbecue

Music Hall of Fame: Kenny Chesney shot part of the video for his hit "No Shoes, No Shirt, No Problems" here

Contact: 284-495-9358

*20: typical number of boats anchored offshore in high season

Next: Sonia Rican Restaurant >

Photograph by Julien Capmeil for Condé Nast Traveler