Helene Pines Richman

Sailing Past Scylla and Charybdis: The Aeolian Islands off Sicily

Growing up in coastal New England, in and out of pools and surf, often sparks a yen to sail and for me, one I have had for most of my life. Trips to Cornwall in England and plans to learn on the Isle of Wight which never came to fruition kept those thoughts firmly anchored in my mind and were part of a renewed desire to experience adventure and not just mark time in an arc of increasingly acute measure, or at least seemingly so.

So I joined a small but merry band of non-sailors, one able sailor and his wife, and a friendly and knowledgeable skipper for a magical week on board a catamaran on the Tyrrhenian Sea visiting the volcanic Aeolian Islands off the northeastern edge of Sicily, past mythical Scylla and Charybdis. The availability of this experience was the brainchild of Warren Marland, our able sailor, originally from Manchester, UK, who made Aliyah decades ago and had a dream to bring sailing to shomer shabbat folk who probably didn’t know a jib from a mast but wanted to learn.

This trip is pitched as seven volcanos for seven days but it was so much more than that, though to be sure, the volcanos were supremely awesome and justifiably deserving of star billing.

The adventure started at a marina a few hours east of Palermo and north of Catania and Taormina, all places of fascination and well worth a visit. Sicily has a long and complex history of being overrun by one people after another and a marked Jewish presence if one looks. Jews were probably there from the end of the ancient Greek era, there is a preserved mikvah in Siracusa, and later on established communities were dotted across Sicily. There is a medieval Jewish quarter in Trapani but like the Iberian Peninsula, Jews were forced to leave or go underground during the Inquisition, which sadly came to Sicily, unlike the rest of Italy.

Back at the marina, first you have to walk a plank to get on the catamaran, and it moves. Everything does. The sea is like that. But you figure it out, and the skipper helps you and you successfully leave terra firma for your temporary home at sea. And you begin to adjust to the constant bobbing up and down, the need to be careful when you walk or climb, and the relaxing feeling which completely engulfs you. I loved the sensation.

Days generally started early and watching daybreak on a double hulled sailboat surrounded by the sea and other sailboats with jagged islands of rock and greenery in the near distance is a stunning sight and well worth waking up to just after dawn. Each day offered the opportunity to swim in the sea, a kind of cerulean blue, changing to emerald green or aqua in different light, learn to paddle surf on a board, and snorkel. One day involved the added excitement of me swimming with jellyfish, which I did in a swimming costume with long sleeves and leggings (all UV 50), and anti-jelly fish cream which I slathered all over any remaining exposed skin. It worked just fine. The jellyfish were exceedingly pretty to see but they didn’t sting me.

Also on the same day, some of us snorkelled out to an area with underwater plumes of effervescent gas emanating from volcanos under sea. I don’t think I have seen anything else so beautiful and unique in the natural world. This must be where mermaids live, an ancient archipelago which summoned Homer’s Ulysses so long ago. If you listen closely, like an ear to a seashell, you can hear their siren song.

Every day we also made for land and explored different islands:- Volcano, Panarea, Stromboli, Lipari and Salina, each with a different atmosphere, some with lovely shops and cafes. Stromboli is the biggest volcano and at night we climbed to see its eruptions live, bursts of red fire at the acme, descending in a remarkable glow.

We spent Shabbat in Lipari and met up with a friendly American family also catamaraning in the Med and in late afternoon took a two-hour tour of the town guided by a friendly expert who shared its fascinating history which predates the Greeks. With lots of early medieval to late baroque buildings to appreciate, we also saw beautiful black sand beaches and had the opportunity to collect obsidian and pumice stone on the sand and rock.

These islands are indeed some of the most unusually lovely, with a local culture and cuisine said to be among the most distinctive in Italy. We tried to capture its taste with our own cooking, which was a team effort – ship’s galley-made pasta, pizza, the freshest fish imaginable, purchased off the side of the boat from local fishmonger Marco, luscious cheeses from Israel, and Warren, aka challah braiding maven, demonstrating one of his many talents. And yeah, we learned about sailing.

I was very lucky to be with a friendly group who really got along well. A repeat annual trip would be most welcome. The beautiful islands of the world beckon and there is nothing to beat swimming wild in warm blue seas and dining kosher afterwards.

Helene Pines Richman © 2026

About the Author
Helene Pines Richman grew up in the Connecticut countryside outside of New Haven, went to UPenn, then law school in DC, moved to NYC, became a lawyer, imbibed the Upper West Side and planned to make aliyah. In 1990, she made it more than half way, relocating to London. She has 3 grown children, grandchildren and a life as a barrister and lecturer in law. But she still has her dream of Jerusalem and she's on her way.
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