This blog is probably unnecessary. As if you need to be convinced. Even without my carefully crafted highlights, you already know you want to sail in Sicily even if you aren’t sure why.

I’ll tell you why.

Martin Scorsese. The Godfather. Specifically, The Godfather II and those early scenes of the dusty, simple Sicilian countryside juxtaposed against the intrigue of the honor-forward, ruthless Cosa Nostra. Either that or you just crave good Italian food and relaxed, uncomplicated island-to-island sailing.

Your initial motivation doesn’t really matter, because by the time you leave, you’ll have an entirely new list of why you are glad you went and why you can’t wait to go back.

Things we loved most about sailing in Sicily? Here are the top ten.

1 – The Mainland

The Aeolian Islands alone are reason to go. But while you are there, carve out at least a few days on the mainland. A week is best if you can make it happen. That is enough time to circumnavigate the perimeter of Sicily soaking in the beautiful countryside, old world traditions, Sicilian delicacies, ancient relics, and excellent wine. Public transportation is available, albeit somewhat limited. No matter, you can make it work, or get an International Driver’s License and take off in one of the comparatively inexpensive rental cars.

2 – Volcanoes

Counter-intuitive, I know. I am not going to lie, the video of the little sailboat speeding away from an erupting Stromboli two weeks before our trip did give me pause. But you can’t truly appreciate or enjoy the Aeolian Islands without giving a nod to their literal upbringing. And if you go to the Island of Vulcano, which you should, you’ll be able to hike up and safely experience the light puffing of gasses into the air. Some members of our flotilla sailed to Stromboli keeping a two nautical mile, coast-guard enforced distance from the shore to get a closer look. We stuck to the views from the island of Panarea where, at night, we could see the red glow of Stromboli’s lava in the distance.

3 – Uncrowded Sailing

Perhaps our best surprise about sailing off the coast of Sicily was the perfect number of boats on the water (we were there in mid-September). Enough to make you feel like it was ok to be there but never so many sailboats that you needed to battle for anchorage space or be constantly on guard determining right of way on crowded waters. The Goldilocks sailboat situation made for relaxing days and we never really worried about who was sailing where. There was plenty of space for everyone.

4 – Relaxed Seaside Towns

The small towns we encountered at each stop were one of the biggest highlights. My favorite? Salina. The shops with handcrafted items, charming pathways, the high break wall that you could climb up then walk down to admire the safe harbor on one side and the ocean on the other. Panarea’s San Pietro with it’s charming white buildings and views of Stromboli in the distance were a close second. Like many European sailing areas, every place we anchored or moored had it’s own personality and unique appeal. Each a bit different, each a place we would visit again.

5 – Having Your Wish Come True

Our flotilla guide Roberto told us about the arch near the caves on Filicudi across from La Canna, the big tall rock jutting out several hundred meters from shore. Apparently, if you swim through the arch and make a wish, your wish will come true. One wish per swim, so of course, I had to go back and forth a few times. My last wish was for wind because we had joked about it that morning when we heard about the arch. Up until that point, there hadn’t been more than a light breeze. After we finished swimming and visiting the caves, we headed toward our destination for the night, Lipari, motoring in zero wind. After about an hour the wind picked up and HOLY COW WIND! We reefed our sails, a possibility we would have laughed at just hours before, and had an exhilarating sail. Bottom line, the wish thing is real, and I am now patiently and eagerly waiting for my other wishes to come true!

6 – The Food and Wine

Master of the obvious, I know. And, by disclaimer, I will tell you that we *were* on a wine and culinary flotilla, so even more obvious. But that doesn’t mean it should be left off the list. The culinary part of Sicily is not to be missed. Pasta for days, the freshest seafood, and my personal favorite, arancini which are lightly fried risotto balls with delightful things inside ranging from a meat filling to chocolate. Our friend and crew-mate Matt who sailed with us is also a trained chef, and everything he makes is better than anything you have ever tasted, so we were pretty much covered from morning ‘til night with delicious food.  (Related:  If you need a great boat chef who has his sailing certs and also looks like a Men’s Fitness Magazine model, I can hook you up). Beyond the food, the wine was even better. In Palermo we found a small Enoteca that served excellent Sicilian wines. We can’t remember drinking a better Merlot anywhere, especially for such a reasonable price.

7 – The Caves

Remember the arch and the wish? Well the entire reason we went to that spot on Filicudi across from La Canna was to visit the cave, which did not disappoint! You’ll want to anchor North of the arch if conditions allow, then take your dinghy to the cave. Going through the arch works just fine. The cave will be right there and if you go at noon, the light will be perfect. Just make sure to turn off the motor and paddle in. There are other caves too, and our favorite was the last day of the trip on the West side of Vulcano on the way back to the Portorosa Marina. The cave is beautiful, the water incredible, and the pool of Venus is simply lovely. Definitely worth a stop!

8 – The Mid-Day Stops

The caves deserve their own spot on this list of favorites, but the other mid-day stops were equally terrific. On the way from Vulcano to Panarea we stopped at Lisca Bianca for snorkeling with the promise of seeing the volcanic gas vents on the ocean floor which emit bubbles from the ground. At first, we saw a tiny bubble trail, and thought “this must be it”, but then a member of our group found the real bubbles – really big bubbles – and it was fantastic! Large streams of bubbles, side by side, racing to the surface as we swam through them amazed. We also went to the beautiful cove where scenes from the movie Il Postino were filmed. You’ll see a gorgeous arch as you round the corner into the crystal clear bay. Be careful, though, the bottom can be rocky and you’ll want to anchor as close to the swim line as possible. We sent our friend-chef Matt into the water with a mask and snorkel before anchoring to inspect the holding. Many sailors were not as careful and snagged their anchor chains around rocks. If this sounds too dicey, no problem. The options for mid-sail stops near black sand beaches and charming towns are seemingly endless.

9 – The Sunrises

The sunrises were picture perfect, almost rivaled by the sunsets depending on the anchorage. I realize this is no different, really, than sailing just about anywhere as sunrises, sunsets, and sailing go together. In Sicily it is the same. You wake up with Mother Nature showing off and end your day with her punctuating the fact that she really is pretty good at her job. Honestly, it never gets old.

10 – On Land Excursions

If you love sailing, the sailing is the best part. That kind of goes without saying.  But don’t overlook the value of spending a bit of extra time at each anchorage or mooring to see what the Aeolian Islands have to offer. Many of the islands have well-marked hikes, often with big rewards. We anchored in southern Baia Milazzese on Panarea and in the morning, dinghied to shore and took the short hike up to Punta Milazzese to see the ruins of a prehistoric village dating back to the bronze age. Incredible! The volcano hikes found on each island are always worth the effort.

Bottom line: If you are seeking uncomplicated sailing paired with experiencing a culture deeply rooted in tradition and a fascinating history, make certain that Sicily is on your list.







Lea Maxwell is the sailor and scribe behind Escape Under Sail, a web|blog project that connects new and future bareboat sailors with the resources, information, and motivation they need to competently and confidently sail beautiful destinations around the world.

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