Yacht & Catamaran Charter in Portorosa, North Sicily, Italy

6-day Sailing Itinerary from Portorosa

The Aeolian islands are a dramatic, but beautiful and tranquil place to sail. Whilst the whole area is undoubtedly dominated by the volcanoes of Etna, Vulcano and Stromboli, you'll find secluded bays, pristine beaches and something to like in almost any direction you go.

Our six-day itinerary covers 105 nM and ticks off all the key islands in the Aeolian, with the exception of Stromboli (where there isn't a marina, for obvious reasons). It’s only a six day itinerary because you’ll normally check-in on Saturday afternoon, and once you’ve got provisions on board and sorted, there isn’t usually time to get any meaningful sailing in. You’ll also need to bring the boat back on the Friday night (before checking out on Saturday morning) – so six days of sailing. But don’t worry, we can make them count!

105 nM means a leisurely-paced week - you’ll be sailing 4-5 hours a day, which leaves plenty of time to explore beautiful Vulcano, pristine Salina, Lipari, the wildlife paradise of Panarea, and medieval Milazzo – which are the best bits that the area has to offer.
 

 Day 1. Portorosa to Vulcano – 19 nM 
Ciao! What a wonderful day to start a sailing holiday! The sun is in the sky, the prevailing summer wind should be arriving from the north-west, and the sea is calling to us! Round up the crew, get the provisions on board, and let’s get this show on the road. Nudge out of the marina, remind the crew how to get the sails up, and point the nose of the boat at the nearest island you can see.

It’s possible to make the traverse to Vulcano in one tack, but better to break the crew in by giving them plenty of practice. Vulcano, as the name suggests, is a picturesque volcanic island. It was last active in 1890 and it’s possible to hike to the crater and back in around three hours – you also get a fantastic view of the Aeolian islands from up there. If that sounds too strenuous, then Vulcano is also famous for its thermal mud baths (a short walk from the port area) – the mud has a strong smell of sulphur, but is reputed to take years off your appearance – or its beaches.
 

 Day 2. Vulcano to Salina – 13 nM 
If you thought one volcano was impressive then you’re in for a treat, because our next stop, Salina, has two! To get there, we’re skirting around the largely undeveloped west coast of Lipari (we’ll see the other side of Lipari in a few days time).

Despite being the second-biggest of the Aeolian islands, Salina is the greenest and quietest, so it’s a nice place to relax. As well as the pretty village of Santa Marina Salina itself, complete with a few churches, museums, restaurants and gelaterias, there’s also the prehistoric village of Portella to check out – the settlement of 25 circular houses dates back to 2000 years BC and is remarkably well preserved.
 

 Day 3. Salina to Salina (via Panarea) – 23 nM 
Almost all PlainSailing.com itineraries head to a different port every night, but today, you are the exception to the rule: we’re planning on coming back to Santa Marina Salina tonight, so why not go and see if you can make a reservation at that cute restaurant that you only spotted too late last night? The local speciality in Salina is basically anything which uses their locally grown capers.

That doesn’t mean that we’re not doing any sailing, however – we’re reaching across the prevailing wind to sail around the island of Panarea, a tiny remote island which is home to all sorts of wildlife, including whales and dolphins. You can turn around once you’ve spotted one, or stop at Panarea to swim at an idyllic beach (the cala junca beach on the tip of the south coast is the best in the area), snorkel near coral reef, or grab a bite to eat (the island itself is a bit of an expensive honeymoon destination and has a reputation for being a hideaway for VIP’s and the super-rich, so you might also spot a few superyachts in the waters nearby).
 

 Day 4. Salina to Lipari – 11 nM 
It’s only a short hop from Salina to Lipari, the biggest and most populated Aeolian island, and it’s potentially the only chance you will have to goose-wing with the wind plus there are bays and crazy white beaches en-route which are worth stopping at for a dip or a snorkel. Lipari is the capital of the Aeolian, and most ferries and hydro-foils to and within the islands come via here, so you’ll spot more land-lubbing tourists here than on the other islands.

The island is best known for its sweet Malvasia wine (there are plenty of shops in the village where you can sample the local produce, or you can head out to tour a local vineyard). It’s possible that if you ever bought a pumice stone in the UK prior to 2007, it came from the pumice mine here – they used to export pumice all over the world. The island only stopped pumice-mining after Lipari was declared a UNESCO World Heritage site (but best not to bring it up with the locals, as the decision was very, very unpopular at the time, including violent mass-protests in Messina).
 

 Day 5. Lipari to Milazzo – 23 nM 
Today we’re leaving the Aeolian islands to return to Sicily – which means that if you haven’t gotten a team picture of sailing through the islands, then today is the day. If you time it right, then you should be able to get a great shot of the crew sailing in front of a distant Vulcano. It’s a shame that we couldn’t take in Stromboli, where there is magma and smoke, but it’s a long slog of a sail away, and it’s supposed to be a holiday!

We’re running with the prevailing wind to Milazzo, an ancient Greek settlement which Ulysses visits in Homers Odyssey. There’s a magnificent medieval castle that protects the old walled town and dominates the new town and marina below. There’s also good restaurants, a great seaside promenade, and, of course, great beaches.
 

 Day 6. Milazzo to Portorosa – 16 nM 
It’s sad, but today is the last day of sailing. Hopefully you’ve appreciated the sheer beauty of your travels in this largely undiscovered part of the world – be careful not to tell too many people about it, or they’ll all be out here! But there’s still one day of sailing to go, and it’s a fun sail along the Sicilian coastline, tacking into the wind, and looking super-cool to all the beach-goers you sail by.

You’ll need to visit the fuel berth on the way back into the marina, before taking your trusty vessel back to where you found her. Someone will be over to inspect the hull and check she is all in one piece, but you can stay on her overnight and you’ll need to check-out in the morning.

The local and marina bars should be buzzing with lots of sailors exchanging tales of their adventures from the last week, so get out there and join them. And maybe have a last glass of Malvasia to toast your week away. Hopefully the sunshine and sailing has helped your crew to bond into a fellowship, and you’ll already be planning your next sailing adventures – if you need inspiration on where to go, come and read the other destination guides at PlainSailing.com. Get home safe, and see you soon!