The British Virgin Islands have earned their reputation as the world's premier sailing destination — and after years of sailing there, I can tell you that reputation is well deserved.
What sets the BVI apart is the infrastructure. Moorings are plentiful and well-maintained. Provisioning is straightforward. The charter industry is mature, which means you have access to well-maintained vessels and professional support if anything goes wrong.
The sailing itself is genuinely pleasurable. You can island-hop between Tortola, Virgin Gorda, Jost Van Dyke, and Anegada without ever spending more than a few hours underway. Each island has its own character. The Baths at Virgin Gorda are unlike anything else in the Caribbean. Jost Van Dyke's Great Harbour is one of the most social anchorages in the world.
If you are planning your first charter, the BVI is where I would send you.