BVI is the easiest first-time bareboat — line-of-sight navigation between Tortola, Norman Island, Cooper, Virgin Gorda and Anegada, 25-30 mooring buoys per anchorage, all passages 5-15 nm. Bahamas (Exumas) rewards longer crossings with empty sandbars, swim-with-pigs at Big Major Cay, and Thunderball Grotto — passages run 15-30 nm with the occasional 40-50 nm jump to Eleuthera. Grenadines (Martinique → Grenada) packs the densest snorkel anchorages in the Caribbean — Tobago Cays Marine Park, Bequia, Mayreau, Mustique — with 5-12 nm hops between islands and the most cultural variety: French Creole, British, independent island states all on one week.

Plan 3-4 hours under way most days and anchor by early afternoon for swimming, snorkelling and sundowners. BVI averages 5-15 nm passages — Tortola → Norman → Cooper → Virgin Gorda → Anegada → back. Bahamas Exuma chain runs 15-30 nm between cays with the Nassau-to-Eleuthera or Nassau-to-Andros crossings stretching to 40-50 nm. Grenadines packs 5-12 nm island-hops between Bequia, Mustique, Canouan, Tobago Cays and Union. With 15-20 knot trades on the beam most passages are sailed not motored.

A one-time $300 USD permit on arrival at the port of entry (Nassau, Marsh Harbour, Bimini) covers a 12-month cruising and fishing licence for yachts up to 35 ft; vessels over 35 ft pay $500 USD. All foreign-flagged yachts entering Bahamian waters must clear in within 24 hours of arrival — fly the yellow Q flag until cleared. Departure clearance is also required. If you charter a Bahamian-flagged catamaran from Nassau or Palm Cay the boat is already permitted; no separate fee.

Caribbean trade winds blow east-north-east at 15-20 knots December through May, dropping to 10-15 knots June through November. The Christmas Winds reinforce trades to 20-25 knots from late December to early January — booking around that window is the trade-off between strong reaching conditions and busier anchorages. Atlantic hurricane season runs 1 June - 30 November (peak August-October). Most charter insurance excludes named-storm-zone cruising July-October, restricting BVI / Bahamas / northern Antilles charters. Grenada and Trinidad sit below 12°N — outside the main hurricane belt — so the southern Grenadines stay open year-round with minor insurance surcharges.