Routes: Connect the Ports

Start with time, not distance

The most common planning mistake is to begin with a list of places and then try to join them up. A steadier method begins with time. A typical charter week offers six sailing days once you account for boarding and the final return. Decide first how many hours a day your crew genuinely wants to be under way. For many groups with children or new sailors, three to four hours feels comfortable; experienced crews may enjoy six. At a cruising monohull’s usual speed of five to six knots, that gives a realistic daily range, and only then should you look at the chart.

From there, sketch a rough shape. Mark the base, draw a circle representing a comfortable day’s sail, and see which harbours fall inside it. The coast you chose will show its character quickly: in the Ionian, a dozen anchorages may fall within one circle; on more open coasts, you might find two.

Loops versus one-way passages

A loop returns you to the base where you began. It is simpler, avoids one-way fees and lets you shorten the route if the weather turns. A one-way passage, such as sailing Split to Dubrovnik, covers more varied coast without retracing steps, but it commits you to a fixed final destination regardless of conditions. Many skippers prefer a loop for a first visit and a one-way route once they know a region.

Sample sequence: central Dalmatia loop

1. Split → Milna, Brač

   A short opening leg across the channel to a protected harbour.

2. Milna → Hvar Town or the Pakleni Islands

   Anchor among the Pakleni islets if you prefer quiet to town life.

3. Hvar → Vis

   The longest, most open leg of the week; plan it for a settled day.

4. Vis → Komiža and back east

   Time ashore on Vis rewards a slow day.

5. Vis → Šolta → Split

   Close the loop with short legs and margin to spare.

Sample sequence: Ionian Inland Sea

1. Lefkada → Meganisi

   An easy first hop into sheltered bays.

2. Meganisi → Kioni, Ithaca

   Crossing open water toward Ithaca with the afternoon breeze.

3. Ithaca → Fiscardo, Kefalonia

   A short channel crossing to a busy harbour; arrive early.

4. Kefalonia → Kalamos → Lefkada

   A return through quieter islands.

Sample sequence: BVI circuit

A typical circuit from Tortola runs east along the Sir Francis Drake Channel to Virgin Gorda for The Baths, north to the anchorages around Gorda Sound, then west to Jost Van Dyke and back via Norman Island. Distances are short; the planning challenge is mostly about timing mooring arrivals and, if you go, navigating Anegada’s reef in good light.