Our Complete Sicily & Aeolian Islands Itinerary
A journey of volcanoes, sailing, medieval towns, wine and pistachios
This unforgettable trip combined the beauty of the Aeolian Islands with the charm of Sicily’s mountain villages, local food traditions, and unforgettable wine country. Here is our complete day by day itinerary.
Day 1 Arrival in Catania Taormina (Hotel Continental)
We landed in Catania, picked up our rental car, and drove to Taormina to check into Hotel Continental, a welcoming hotel with spectacular rooftop views of Mount Etna and the sea.
Highlights
- Corso Umberto evening walk
- Views from Piazza IX Aprile
- Dinner in Taormina’s old town
Day 2 Taormina to Portorosa (Check into Sailboat)
In the morning we visited the Greek Theater and walked Taormina. We drove to Portorosa Marina and checked into our sailboat for the week. The rest of the day was spent provisioning the boat, organizing cabins.
Where we stayed:
Sailboat, Portorosa Marina
Day 3 Sail Portorosa to Lipari (Overnight in Lipari)
Our first sailing day took us to Lipari, the largest and liveliest of the Aeolian Islands.
About Lipari
Lipari is colorful, friendly, and full of energy the perfect introduction to island life.
Highlights
- Pastel marina promenade
- Famous pumice coast
- Walking the old town and citadel
- Gelato, cafés, and seaside strolling
- Wonderful dinner
- Docked in the marina for the night
Read more about our time in Liapri
Day 4 Lipari to Stromboli (Buoy Field) + Night Hike
Next, we sailed to dramatic Stromboli, home to one of the most active volcanos in the world.
About Stromboli
Raw, powerful, and unforgettable a smoking cone rising straight from the sea.
Where we stayed:
Buoy field off Stromboli (sleeping on the boat)
What we did:
Stromboli night hike, read about this adventure:
- A sunset ascent
- Watching glowing lava bursts
- The famous Sciara del Fuoco
- Hiking by headlamp at night, and breaking my hand!!
- Returning to the boat with the volcano erupting in the darkness
An unforgettable highlight of the entire trip.
Day 5 Stromboli to Salina
We sailed to peaceful, green Salina, known for wine, capers, and quiet island life.
About Salina
The lushest island in the Aeolian chain calm, scenic, and perfect for slow travel.
Highlights
- Vineyard covered hills
- Capers and Malvasia Wine
- Small, charming villages
- Relaxing marina surroundings and fishing boats
Where we stayed:
On the sailboat in the Marina in Salina
Day 6 Salina to Vulcano
Next, we sailed to Vulcano, a rugged, volcanic island with a dramatic landscape.
About Vulcano
Raw and otherworldly sulfur vents, black sand beaches, and steaming crater walls.
Highlights
- Volcanic scenery all around
- Quiet night on the water
Where we stayed:
Buoy Field On the sailboat, dinner on the sail boat. We purchased fish from a local fisherman
Day 7 Vulcano to Portorosa (Final Night on the Boat)
We sailed back to Portorosa and spent our final night onboard, giving us plenty of time to pack and prepare for turning the boat in the next morning. We had to return one night early because of bad weather
Where we stayed:
Sailboat, Portorosa Marina
Day 8 Portorosa, Castiglione di Novella, Castiglione di Sicilia (Hotel Federico)
After checking in the boat, we began driving inland. Along the way, we made a scenic stop in Novara di Sicilia, a beautiful Italian village
We continued to Castiglione di Sicilia and checked into Hotel Federico, a historic medieval property in the heart of the village.
About Castiglione di Sicilia
A beautiful hilltop village overlooking Etna’s wine country stone alleys, ancient walls, and breathtaking views.
Highlights
- Wandering the medieval streets
- castle
- Enjoying the sunset over Etna
- Staying at Hotel Federico
- Apertivos and Dinner
Day 9 Castiglione to Randazzo (Parco Statella) + Etna Wineries
We checked into Parco Statella, a charming agriturismo surrounded by vineyards and a family farm that has been in the family for 500 years. Along the way to Parco Statella we explored Linguagloosa and visited Gambino Winery. We had lunch at Cave Ox and also while in this area visited Tenuta di Fessina. Click here to read more about the Etna Wine Road
About Randazzo
A dramatic medieval town built almost entirely from black lava stone atmospheric, historic, and close to Etna’s northern slopes.
Where we stayed:
Parco Statella, Randazzo
Day 10 Randazzo and Bronte
We visited Randazzo in the morning, lava stone streets and churches. Sunday Market in Randazzo was also going on while we were there. We had lunch at Veneziano then we drove to Bronte, the pistachio capital of the world. Famous for the highest quality pistachios on earth bright green, intensely flavorful, and grown on volcanic soil. Click to Read more about our side trip to Bronte.
After exploring Bronte, we returned to Parco Statella for one last peaceful night in the countryside. We had dinner at San Giorgio and the Dragon
Day 11 Silvestri Craters, Catania Fish Market, Airport
On our final day, we visited Zepherna Etnea where we purchased local honey, we then drove up Mount Etna to walk the Silvestri Craters, an otherworldly landscape of black and red volcanic rock.
From there, we headed into Catania to experience the iconic La Pescheria fish market, full of energy, seafood stalls, and local produce the perfect ending to our Sicilian adventure.
Returned the rental car and flew home.