Travel /

Sailing Sicily Off Season Pt.1: A Trip Around Italy’s Biggest Island



January 1st, 2022 - Capo d’Orlando to Lipari 

nautical miles: 29

weather conditions: overcast with light breeze


In the first few days of December Paolo suggested we embark on an adventure which combined our common passions: a gastronomic sailing trip around Sicily. Our shared love for food, cooking, meeting producers, talking to people and a general appreciation of the sea are, after all, what brought us together in the first place. 


After much planning and research, we decided to set off on our trip on January 1st, 2022: new year, new adventure. I’d been craving an “adventurous holiday” ever since the start of the pandemic and he was just happy to sail all day, every day. The beauty of traveling with one’s own accommodation is that you can be completely flexible, changing route whenever you please. Our only non-negotiable item was our deadline: we had to be back home on the 20th of January. 


20 days to circumnavigate Sicily, Italy’s biggest island. 


We set sail around mid morning of the first day of the year, completely hungover from the previous night’s celebrations and forgetting half of our equipment at home – I couldn’t imagine a better start!


January 2, 2022 - Lipari via Salina to Filicudi 

nautical miles: 23

weather conditions: overcast, no wind


The day always begins with a freshly-squeezed orange juice from the 25kg of oranges (which we fortunately didn’t forget on land) from Paolo’s garden in Salina.


With Vulcano puffing away in the background, we set off towards Salina, the greenest of the Aeolian Islands. Just outside Santa Marina Salina is a stretch of pebble beach dotted with little white houses decorated with all sorts of souvenirs from the sea. As we dragged our dingy up the beach, we were welcomed by Oscar, fishmonger and one of the 2000 year-round inhabitants of the island. His first inquiry was whether we wanted a glass of Amaro del Capo. We looked at our watches, which read “10AM”, but decided it was too impolite not to accept the offer. With our iced Amaro in hand, Oscar began showing us the various options of fresh fish and after a brief discussion on weights and prices, we settled for 5 kg of mussels and one scorfano (redfish). With quick, expert motions our new friend began cleaning the fish for us, using just a wooden plank on a tree stump as a worktable. He emptied out the innards in the sea, where five greedy seagulls awaited their breakfast. 


The rest of the morning was spent cleaning and selecting the mussels, throwing any bad ones straight back into the sea, as we sailed around Salina. Once cleaned, we placed the mussels in a large pot with a few smashed garlic cloves and plenty of olive oil for them to steam and open. Lunch was a bowl of steaming, fresh, meaty mussels and liters of salty sughetto, perfect for scarpetta


We arrived in Pecorini a Mare, Filicudi’s most colorful neighborhood, with a few hours of sunlight to spare—time to explore the island by foot! I was already familiar with the beautiful island but seeing it without boats and people (off-season) felt like looking into a treasure few people have access to. We climbed between cacti, volcanic rocks and olive trees until Capo Graziano—the island’s most Eastern point which is home to prehistoric settlements and stunning views. Feeling parched from our hike, we trailed up Filicudi’s only paved road in search of the only bar open throughout winter: a completely deserted, family-run affair. A kind nonna was sitting on a chair, half-asleep, and welcomed us with open arms, calling her grandson immediately and ordering him to come at once to make us an aperitivo. Minutes passed and no one showed, so we told the signora not to worry and helped ourselves to a bottle from the fridge and four glasses. As we sipped our wine, nibbled on the island olives and chatted, the bar began filling up with people: Sunday mass was over and it was time for a quick aperitivo


We sleepily strolled back to the boat and talked about the delectable dinner awaiting: calamarata con scorfano alla Eoliana, a tomato sauce with onions, capers and olives commonly used as a base in the Aeolian Islands, to which we added the fresh redfish filet. 

Photo by Giorgia Garancini

Photo by Giorgia Garancini


January 3, 2022 - Filicudi to Cefalu

nautical miles: 41 

weather conditions: overcast, strong winds with an afternoon shift: sunshine and no wind


The humidity woke us up, it seemed like everything was drenched in water! So we set off slowly and shivering towards Cefalu, waving goodbye to the Aeolian Islands. Towards mid-morning, halfway between the islands and mainland Sicily, we spotted the sun ahead of us. The wind was pushing the clouds away and soon we would be bathed in sunlight, after three days of dark clouds: pure joy! Reaching the sun felt like being born again – it transformed us. We turned up the volume on the speakers, switched to a reggaeton playlist and began dancing and singing, celebrating the sun. Suddenly, Paolo jumped up, shouting and pointing at the sea “eccoli!!” We followed his finger and began quivering with a child-like enthusiasm: the dolphins were arriving. We ran to the boat’s bow, turned off the music and began whistling, to summon them. The dolphins arrived jumping, playing with the boat’s waves and angling their bodies, as curious to see us just as we were to see them. Then suddenly, as quickly as they arrived, they disappeared deep into the sea. 


We resumed our dances to the tunes of the 2000s greatest hits and sailed into the sunset, nestling ourselves in the protected bay of Cefalu’s old town for the night – a mooring forbidden in summer!

Photo by Giorgia Garancini


January 4, 2022 - Cefalu to Palermo

nautical miles: 35 

weather conditions: clear skies and no wind


After a light breakfast consisting of cassata, ricotta-filled cannoli and sfoglie stuffed with crema al pistacchio under Duomo’s shadow, we waved goodbye to our friends who joined us for the first leg of the trip. Basking in the sun, without a cloud in sight, we set off for Palermo, Sicily’s largest and busiest city. 


We dedicated our first night in Palermo to a street food scavenger hunt, tasting all the city’s specialties, from stigghiole (guts wrapped around a leek and grilled) to the more vegetarian-friendly pane, panelle e crocché (bread with fried squares of chickpea flour and deep fried potato croquettes). We sat around a small table at Antica Focacceria San Francesco and ordered a panino di panelle and one pani câ mèusa maritatu. The latter is a Palermitan street food delicacy par excellence, consisting of slow cooked innards (most commonly veal spleen and lungs) spooned into a sesame seed bun with a thick layer of ricotta. A generous serving of caciocavallo is grated on top and voilà—time to eat. I won’t delve into the details of what this gastronomic experience entailed, but after one hard-to-swallow bite, I decided to stick to pane e panelle. 

Photo by Giorgia Garancini


January 5 - January 6, 2022 - Palermo 

nautical miles: 0 

weather conditions: clear skies and above average temperature


A last minute change of plans compelled us to spend an extra day in Palermo – so we celebrated by having two breakfasts. I remembered eating one of the softest, most delicious Iris a few years ago and after discovering that Paolo had never tasted it, decided it must be the first item on the list of breakfast foods. We jumped on the graziella – the faithful bicycle that would allow us to travel faster via land throughout our trip – Paolo at the pedals and me standing on the carrier and headed towards Pasticceria Costa, a Palermitan institution. 


L’Iris al forno is a baked, donut-like pastry filled with sheep’s milk ricotta and chocolate drops. I imagine it is the closest we can get to biting into a cloud, and you’re bound to get your hands and face covered in a thin layer of confectioner’s sugar which is sprinkled onto the Iris as a finishing touch. Our next stop was a novelty for me, a tiny shop nestled within a courtyard selling all sorts of fried and baked savory goods. I Cuochini is a historic Palermitan establishment, which sells-out around 11AM every day of the year. We filled a bag with as many goodies as they offered and found a table in the sunshine to enjoy our tasting. Each baked good was better than the next, from sweet biscuits filled with piping hot ragù and peas to fried dough balls stuffed with mozzarella and prosciutto cotto. The ride back to the boat was slightly wobbly, with all the added weight of our two breakfasts lying comfortably in our stomachs. 


We spent the rest of the morning trailing around Ballarò market, picking the best olives amongst a myriad of varieties and selecting the freshest cime di rapa and fennel. Without all the summer mayhem, Ballarò turns into an almost local market where one can browse calmly, rather than marching in line covered in sweat. I vividly remember a wedding in the most beautiful church near the market from my trip two summers ago, and I had longed to go inside. Fortunately this time, no one was getting married and we got to explore. We peeked into Chiesa del Gesù di Casa Professa which welcomed us with a breathtaking sight and began our exploration. I’ve seen a lot of churches in my life but this was like nothing I’d ever seen before: over a white background are thousands if not millions of stuccos and marble carvings. The slanted morning light that seeps in through the stained glass windows creates an aura of magic that stuns all. 

Last item on the agenda was to buy a map of Sicily where we could draw our itinerary around the island. We headed to La Libreria del Mare, a quaint bookshop right beside the port filled with everything from sea-themed novels to historic nautical maps. Bingo! Twenty minutes later we walked out of the libreria with a gigantic A1 map rolled under an arm and no clue as to how to carry it on the plane ride back home.


January 6, 2022 - Palermo to Castellammare del Golfo 

nautical miles: 30 

weather conditions: partly overcast, high winds


No breakfast-hopping on our last morning in Palermo. We set off bright and early for a full day of navigation with the small seaside town of Castellammare del Golfo as our destination. Strong winds and choppy seas once again reminded me of the less comfortable and glamorous aspect of sailing, when you spend days at the mercy of weather conditions and always in bolina (on a beat).  We sailed near Isola delle Femmine, surrounded by eager windsurfers and capsizing regatta boats, all the way to Punta Raisi, home to Palermo’s airport which sits right on the waterfront. 


Everytime we reach a new port, my role in the mooring process is to grab the corpo morto (rope, tied on land at one end and to an underwater mooring at the other, which one fastens at the bow to prevent the boat from moving), a task more difficult than it sounds. Today’s mooring was especially complicated as the corpo morto I was handed was the slimiest thing I’ve ever touched. The only act I can compare it to is trying to hold a smooth, slippery fish between your hands. Now imagine having to pull this slime-covered rope in as little time as possible and tie it around the boat’s cleat. It was almost comical: I was pulling in vain, at this point kneeling down to try and create more weight with my body, unable to grasp properly at the rope, as the boat in the meantime tilted diagonally within the mooring space. Paolo quickly reached me with a quizzical look on his face, then suddenly it was two of us pulling a rope coated in slime without much success. Ten minutes later and three thorough washing of hands we were finally tied to the dock and settled in—still covered in slime.  


We spent the rest of the evening at the loveliest bottega con enoteca alongside the port where we enjoyed a delicious tagliere filled with niche Sicilian cured meats and cheese—from suino Nero dei Nebrodi 36 month aged prosciutto – known as the Sicilian pata negra – to a peppery aged Pecorino. To accompany the aperitivo the experienced owners recommended a young, fresh and biodynamic Etna Rosso by Etnella. 


January 7, 2022 - Castellammare del Golfo via San Vito Lo Capo to Trapani 

nautical miles: 31 

weather conditions: overcast with medium-strength winds


After a quick stroll through Castellammare del Golfo’s fresh produce market, we set sail towards Trapani, passing by the famous Riserva Naturale dello Zingaro and stopping for lunch in San Vito Lo Capo. 


Sailing right by the coast in one of the most beautiful parts of Sicily – usually filled to the brim with tourists – is an indescribable experience, reminding me once again of the privilege of an off-season trip. I’d been to the Riserva Naturale dello Zingaro two summers ago, just before its massive fire, and was curious to see its current state. Man-made fires made even worse by the summertime droughts are some of the biggest threats Sicily faces each year. I’m happy to report that nature fought back, repopulating the protected area of the coast with green bushes and plants, although the few larger trees were still visibly scarred and black as coal. We arrived in San Vito Lo Capo’s turquoise bay bathed in sunlight and felt like we were in June—except for the utter lack of living beings in the town which gave it an eerie post-apocalypse feel. 


Like a green oasis in the desert, Gne Sara was open and we were hungry. We ordered the town’s traditional couscous which is served with a wonderful tomato-y fish broth and topped with soft grouper—wonderful! Sicily’s West coastal cuisine has strong links to North African dishes, thanks to decades of migration between the two coasts, transforming typical African dishes – such as couscous – into staples of traditional Sicilian cuisine too. A week-long festival entirely dedicated to couscous takes place every September in San Vito Lo Capo where thousands of tourists flood the small town to try the hundreds of variations of the dish. 


Extremely satisfied by our fish couscous we left the restaurant in search of the other traditional dish we wanted to try: il caldo freddo. An ice cream produced in the area of Trapani and San Vito Lo Capo whose name reflects exactly its nature: hot and cold. A soft biscuit soaked in rum is covered in gelato (usually hazelnut, coffee or pistachio) and finished off with melted, hot, dark chocolate. Despite our efforts to seek this mouth-watering dessert, we quickly realized that not a single pasticceria served il caldo freddo in January (apparently people don’t eat gelato in winter?!). We tried not to let the little gastronomic setback deter us too much and headed back for the boat anchored in the turquoise bay—which had suddenly turned pitch black thanks to the imminent storm. We ran. 


The anchor was lifted and just a few short minutes after we had first seen the incoming storm we were sailing away, fortunately in the opposite direction. Between the sudden adrenaline rush of running away from a thunderstorm on a little boat and the couscous causing me an abbiocco I fell asleep (further testament to my ability of napping in all sorts of situations).