A life-affirming sailing itinerary in Sicily's Aeolian Islands

I’ve longed for years to sail around Italy (or any other equally stunning Mediterranean locale). Jumping into clear, calm, blue, temperate waters is my idea of heaven. The prospect of nothing between me and the deep blue sea, to dive from a boat and swim in silence, with only the sound of my breath, my strokes, turning only to float on my back to squint at the sun and smell the salt. 

To make this dream trip come true, I had to take a chance: join a late-June group sail with Sailing Collective around the Aeolian islands of Sicily. It sounds a bit like a middling reality show (seven nights, five strangers, two hulls, one chance at love). But it was more and better than anything I could have dreamt.

Part 1: Meet your shipmates and crew

One of my nearest and dearest friends, Claudia, joined me on this adventure. We spent a very hot Saturday in Palermo before hopping on the train to Capo D’Orlando, where we spent the night.

In the morning, we received the WhatsApp alert to meet our captain, Dayyan (who coincidentally is the owner of Sailing Collective), our brilliant chef, Flannery, and our 3 fellow travelers aboard the Sonia, a Lagoon 46 catamaran. (One of the guests booked on the group trip had to back out at the 11th hour, so we were light one sailor).

Below Deck, this is not. The staterooms on the catamaran are snug (unless you’re traveling solo). Not gonna lie, I kind of freaked out about space, but it turned out to be more than fine. Claudia and I shared a room with a bed that was a few inches shy of queen, unloaded our gear (storage was tight) and returned topside for our pre-sail conclave.

There we met our fellow travelers: Marshall and Wendi, a lovely couple from Florida who had traveled with Sailing Collective before, and Ashley, a marketing executive from Brooklyn. We realized immediately that Ashley and I live only blocks apart from each other. The five of us listened as Captain Dayyan briefed us on all things safety and pointed out on a large map of the islands ahead of us: Isla Vulcano, Lipari, Panarea, Stromboli, Salina and Filiucudi.

We toasted to our journey and shoved off.

Part 2: 6 days of Aeolian Island-hopping

We departed Capo D’Orlando on Sunday and motored northeast (sailing was dependent on winds cooperating, which they did occasionally) to anchor off the coast of Isla Vulcano for our first swim and a shared “OMG, how is this happening?” moment. Chef Flannery prepared lunch in the tiny galley as we splashed around, overjoyed. We dined on pasta with fresh tomatoes and basil, steamed mussels, prosciutto with melon and wine.

After lunch, we sailed on to drop anchor in a remote area of Lipari called Punta del Perciato where Chef Flannery made an incredible dinner for us: marinated swordfish with garlic, peppers and tomatoes, eggplant caponata and a green salad with roasted red peppers and fresh ricotta. Apart from one other boat, we were all alone, and the sunset took my breath away. We spent the evening drinking wine, getting to know one another and looking up at the stars. 

While Claudia and I have, of late, each had trouble sleeping back home in Brooklyn, we slept like snug babies that first night; being rocked gently to sleep in complete darkness and utter silence was soporific. 

The next day was more sailing and swimming, and on our second night, we hopped into a dinghy to visit Porto di Panarea, a charming, hilly seaside town. We split up: Dayyan and Flannery went to do some provisioning, Ashley and Claudia to shop, Marshall and Wendi to wander while I decided somewhat ill-advisedly to climb up the hill and explore all the little spots along the steep, tiny road wearing sandals that did not grip well.

We regrouped for cocktails on the terrace of Hotel Cincotta before hopping into golf cart taxis to take us up the hill to hidden Trattoria da Paolino where we ate fish, pasta, salads, and drank more wonderful wine as the sun set.

From Panarea, we sailed to Stromboli in search of granita (a typical Sicilian frozen dessert). I did another solo wander through the island’s narrow paths – enjoying some alone time is nice when you’re in such close quarters.

After departing Stromboli, we gaped at the island’s breathtaking beauty, seeing the smoky haze lingering near the island’s active volcano. 

Onward we sailed to Salina, where we ate dinner at a beautiful sea-facing restaurant, Porto Bello. The Spaghetti al Fuoco (spaghetti on fire) was as spicy as it was delicious. 

On our last day we sailed to Fillicudi, my favorite island of the trip. We walked ashore to wander the tiny village of Pecorini a Mare. Afterwards we sailed to the lighthouse islands of La Canna. Our final anchorage was nearly inside a blue grotto – absolutely breathtaking.

Part 3: Return to port

Our final night was the only downside of this trip. The way the weekly charters are organized, all the captains need to return their vessels to the marina on the same day, racing to refuel before docking. 

We ate our final meal on land, back where we started at the marina, a little sad but very happy for the life-affirming moments we shared while on the water.

We said our goodbyes before going to sleep as we were departing at different times early the next morning. 

Part 4: A planning primer

How much does it cost?

The double stateroom Claudia and I shared was more than $7600 (€6471) to be paid in two installments, the final payment due 60 days prior to sailing. Provisioning and tipping are extra, the latter discretionary, but they do ask about it a lot, and since you pay after you return, it feels a bit off after such a wonderful time. I’d have preferred it if they included the recommended 20% gratuity in the fee and requested a deposit for provisioning, drinks and other shared meals on land.  

What did you pack?

We were advised to bring soft-sided luggage – a water-resistant duffel that can also be a backpack is ideal. You need to bring much less than you think, though I did wear almost everything – except the sweater recommended for the chilly evenings we never had. 

 Here’s the packing list that we received prior to sailing:

• Water bottle

• Beach towel (two bath towels are provided, but it's nice to have your own beach towel) 

• Sunglasses 

• Reef-safe sunscreen 

• If you plan on wearing shoes while on the boat, please make sure they are non-skid/boat shoes. Sneakers are not recommended

• USB - A phone chargers (not all the boats have converted to USC - C) 

• European outlet adapter 

• Tote/beach bag to keep your personal items while on deck

• Light, breathable clothing while underway

What if you suffer from motion sickness?

Even if you have a stomach of steel, transferring from land to sea will likely cause at the very least a little wooziness. Marshall, one of my shipmates, had brought a scopolamine transdermal patch (it adheres to the skin behind your ear) to prevent nausea and other symptoms of motion sickness. I had never used one, but I was worried once I got on the boat. I'm not usually a seasick person, but I didn't want to risk it. I experienced no side effects or problems whatsoever while using the patch. That said, consult with a doctor or pharmacist to ensure these options are right for you. Claudia brought along and wore wristbands that prevent motion sickness with acupressure, as well.

How was the boat?

The boat itself is roomy enough to move around pretty easily. We took all our meals around the outdoor table. There was coffee on demand, and there were plenty of snacks (I ate my weight in Nutella cookies). There was always plenty to eat and drink at any time of day. 

The boat had a dinghy and a rickety gangplank, so getting on and off the boat required some dexterity. At one point, I thought I might have sprained my ankle stepping into the dinghy in Stromboli, which would have made the rest of the trip pretty uncomfortable. Thankfully, it turned out to be nothing.

The bathrooms were wee, with a toilet, a sink and a stall shower that made lots and lots of noise when you used it. But there was good pressure and plenty of hot water. You can’t flush toilet paper, so you have to use the garbage can – a bit real for me. 

There were plenty of places to laze about while we were sailing or moored: There was lounge seating behind the cockpit, which was almost always shaded, so I kind of lived up there. There was additional cushioned seating, forward and aft, as well as two nets that served as de facto over-water hammocks, the best seats in the house.