Years ago, my wife, Sandy, and I heard about a clump of islands about 40 miles off the coast of southern Italy, just north of Sicily in the Tyrrhenian Sea—a little archipelago known as the Aeolian Islands. The ragged, volcanic island group includes few natural, protective harbors, but plenty of “sheltered” anchorages that are considered suitable for hooking into, so long as the weather permits. The islands are named for Aeolus, the god who gives Odysseus a sack containing contrary winds midway through the Odyssey. When Odysseus’s crew eventually releases the winds, they blow his ship off course and significantly delay the crew’s return to its homeland.

For many charterers, tricky anchorages and contrary winds don’t paint the picture of vacation perfection. But despite all that, my wife and I still picked the Aeolian Islands to celebrate our 40th anniversary—and we didn’t regret it one bit. 

Getting there wasn’t easy. After two days of travel, which involved airplanes, trains, cabs and quite a bit of charade-like gesturing, we arrived at the Sunsail Charter base in the ancient harbor below the city of Tropea and boarded our 39-foot Beneteau sloop, Chianalea. A friendly Brit was sent over to “help the Americans get on their way,” and we pointed our bow toward Stromboli, 35 miles to the west.

Alas, Aeolus decided to take that particular day off, and we were forced to motor through dead calm waters all the way to Stromboli and its black-sand beach, which stretched out beneath what many consider to be the oldest lighthouse in the world. We’d almost managed to ease into vacation mode, when we were told that our Sunday arrival meant most of the island was closed. Negotiating two dinners of pasta vongole (clams) and red wine was a challenge, but we were determined to take it all in stride. Forty years of marriage has a way of teaching one patience. 

Sure enough, the wind was up the next morning, and we set off for Lipari in a steady 15-knot breeze, which quickly rose to 30 knots (a first reef) and then to 45 knots (a second reef) before ushering us into the harbor. With the help of a friendly ormeggiatore—Italian for the boat-mafia that tends the region’s dock—we managed to successfully dock stern-to, and when the harbormaster informed us that there was a call for Force 7 weather over the next two days, we accepted his “special” price and paid 80 euros for a two-night berth. From dead calm to Force 7 in 24 hours? Aeolus doesn’t mess around. 

It was easy to spend two days in spectacular Lipari harbor, which is lined with lush, green cacti and lemon trees. The main village is just a short walk away, and proved to be a quaint and beautiful community rich in history, with architectural styles spanning many centuries, cuisine inspired from all over the Mediterranean and a most enjoyable selection of Calabrian and Sicilian wines. Visitors get around mostly by cab, bus or on foot.

Following Aeolus’s dramatically windy spree, the breeze returned to a comfortable 30 knots, and we enjoyed a brisk sail from Lipari to Salina and then on to the appropriately named Vulcano, where we anchored in the lee of the island’s still smoldering Fossa di Volcano. As the sun dipped below the watery horizon, we could actually see the orange glow of the lava reflecting off the steam and clouds overhead.

At our next stop, the Island of Panarea, we anchored in a semi-protected bay and took the dinghy ashore for yet another incredible meal—this one featuring Sicilian antipasto, pasta, seafood, goat, pastries and ice cream, all accompanied by carafe after carafe of local red wine. 

Unfortunately, just as the next morning’s wine hangover began to truly kick in, we discovered our anchor had snagged on the base of an old mooring in 25 feet of water, a setback that took several hours (and the help of some friendly but English-challenged Germans on a nearby boat) to remedy. 

Worse yet, by the time we were finally able to limp away from Panarea, our good friend Aeolus had sucked the wind away once again, and we completed the final 40 miles of our trip under motor.

On the plus side, as we were approaching our charter base, the Med served up a hat-trick of entertainment in the form of a 15-minute porpoise show, a veritable migration of brightly colored jellyfish and, finally, a traditional Italian welcome home, complete with boisterous shouting, hand waving and plenty of red wine—not a bad way to end a cruise.

Ultimately, a charter in the Aeolian Islands may not be a charter for everyone. But if you’re looking for adventure, brilliant food, plentiful wine and challenging sailing conditions, this is the place. There’s are a lot of good reasons why they call it “Bella Italia.” 

Which companies charter in Italy?

Phil Vitale lives (and sails) on Birch Lake in southern Michigan. He and his wife, Sandy, have been chartering for over 30 years in the Caribbean, Bahamas, coastal Maine, Florida and Belize