Where the boats actually go.
The same archipelago that makes postcards makes 30-knot afternoons from July to early September — the difference between a dream week and a battering is the order you visit the islands in.
Tortola to Norman, Cooper, Virgin Gorda, Anegada and Jost Van Dyke — short legs, mooring balls, and the Caribbean's most forgiving learning curve.
The Argolic Gulf is Greece's most forgiving piece of water — flat, deep enough almost everywhere, and ringed with bays that take the afternoon wind on the nose so you don't have to.
A week between Sorrento, Positano, Amalfi and Capri works — if the boat moves early, berths are booked ahead, and the fleet treats the 10:00-to-16:00 ferry window as a shore break, not a passage.