“I have only come here seeking knowledge, things they would not teach me up in college,” wrote Sting in The Police’s Wrapped Around Your Finger. In this metaphor-laced song, Sting alludes to ancient myth—Scylla and Charybdis, the twin perils of Homer’s Odyssey, and a sailor passing through the narrow gap between Sicily and the Italian mainland. To sail through it is to pass through the place where the expression a rock and a hard place comes from.

The myths and legends that earned the Straits a place in Homer’s epic remain, while modern-day obstacles—like a Traffic Separation Scheme, complete with a roundabout for big ships—make transiting a novelty that keeps the helm focused.

With a little planning, going through this narrow gap can be a fascinating few hours, with great cruising on either side. In fair weather, there’s plenty to see: swordfish fishing boats with observation towers hunt their prey when it’s calm and open water swimming races take place just off the spit at the western entrance.

Time it right (a simple tide times app makes it easy), and you’ll be swept through at four to five knots. Look closely and you might spot the whirlpools that once struck fear into ancient mariners. In the past—before earthquakes changed the topography—the whirlpools were amplified, gaining a deadly reputation for dragging ships below.

The Messina Straits Pilot official guide (pilotmessina.it) is well worth reading when planning a transit. It includes information on the TSS, who to contact before entering the Straits (something that’s mandatory) and reminds you to keep a listening watch on channel 16 as well as the VTS channel. The Italian Waters Pilot by Rod and Lucinda Heikel is an invaluable guide to cruising Sicily and The Aeolian and also covers The Straits of Messina.

Written by Will Bruton