Mediterranean (Montenegro)

The Bay of Kotor stops you cold the first time you motor in from open water — fjord-like walls of limestone rising straight off the flat sea, medieval Kotor town tucked into the corner like it has been waiting centuries for you to arrive. It has.

This is the most dramatic enclosed cruising in the Adriatic, and because Montenegro sits just south of Croatia's charter crowds, the anchorages feel genuinely quieter from late May through June and again in September.

Wind here is the classic Adriatic maestral — a reliable northwesterly afternoon sea breeze that fills in around midday and gives you clean reaching conditions down the coast. The bora can blow hard and cold off the mountains in spring and autumn, so keep an eye on forecasts if you're anchored in exposed bays north of Budva.

Day sailing is the sensible rhythm; the coast is compact enough that you rarely need to overnight at sea, though the passage south toward Albania or across to Brindisi suits a comfortable night crossing in settled summer weather.

Charter logistics are straightforward out of Tivat Marina, which handles everything from small bareboat cats to skippered gulets. Provisioning is decent in Kotor and the Tivat supermarkets, though prices have risen sharply in recent years. Fuel and water at marinas are reliable.

Sveti Stefan, now a resort island, is best appreciated from the water; drop the hook off Miločer beach and dinghy in for a swim rather than paying resort fees. The paperwork is refreshingly simple — a cruising permit obtained at your first port of entry covers you for the whole country.

May and early June offer the clearest water and coolest hiking conditions ashore; anyone with a low heat tolerance will find August anchorages busy and airless by afternoon.