On the Road: A Sicilian Sailing Itinerary

The ins & outs of a Volcanic Sailing Adventure off the coast of Sicily

Sicily is Great….Sailing in Sicily…Even better.

I’ve done a bunch of sailing trips over the past ten years, but this one stands out. It was September 2021, and a few friends and I set off to explore some Sicilian islands by boat. This version of On the Road ( or water in this case) I wanted to put together a simple recap of the route we took to hopefully inspire you to try your first sailing journey, or plan another one.

There’s something romantic & totally raw about sailing that no hotel can quite replicate. You’re not just visiting a place you’re arriving into it. Quietly slipping into harbors that have seen centuries of travelers before you. Dropping anchor off a rugged cliff in the middle of fucking nowhere, swimming to shore, grabbing a spritz at some sleepy cafe, and then lifting the sails again the next morning to do it all again. It’s immersive in the best, least curated way.

At the end of the post, I’ll break down the general costs, logistics, and why sailing, believe it or not, can actually be a lot cheaper than a week in a fancy hotel. But first, here’s a look back at one of my all-time favorite Itineraries.

General Itinerary

The Aeolian Islands are a volcanic archipelago located just off the northeastern coast of Sicily in the Tyrrhenian Sea. Made up of seven main islands including Lipari, Stromboli, Panarea, Filicudi, Alicudi, Salina and Vulcano. To be honest I didn’t know these really existed til I started to deep dive more on this itinerary as an option to sail.

Getting to the starting point.

We flew into Catania, Sicily the day before departure, rented a car, and made the two-hour drive to Marina Portorosa where the boat and crew were waiting. Everyone trickled in throughout the day, flying in from different corners of the world. It was the first sailing trip for my wife, Paige, and the four friends joining us. They came in blind and just trusted me. There’s nothing quite like the feeling when your friends start showing up to some random marina in Sicily with a duffle bag and no idea what’s ahead. Once everyone arrived, we grabbed some provisions for the week, had a simple dinner by the docks, and called it a night.

Day 1

We set sail in the morning and started to sail to our first destination which was the island of Vulcano. There is a black sand beach called Asino that we set anchor at and our chef Flannery made us an incredible lunch. I brought my trusty “Emergency Negroni” glass flask which I pre mix Negroni in for each day instead of trying to measure out on a rocking boat.

We swam in to the beach where there is a small cafe and sun beds you can rent for a few euros. Backgammon is always a must have on trips like. Sailing trips are the main reason I decided to make my own travel backgammon board. We stayed at anchor the first night in the bay of Asino at Vulcano and enjoyed a family style dinner on the boat. Safe to say this was a nice easy day to settle in and get ready for the rest of the trip.

Day 2