Sailing Sicily: An Itinerary Through The Heart Of The Mediterranean's Alluring Landscapes & Cultural Mosaic
7 Day Sicily Sailing Itinerary
Aeolian Islands Sailing Itinerary
Sicily and the Aeolian Islands: A sailor's dream where the winds of history and nature converge. What sets our Sicily and Aeolian sailing itinerary apart is its depth and authenticity. This isn't just another guide; it's the most comprehensive sailing itinerary you'll find, anchored in real experiences and enriched by local expertise.
From the age-old streets of Palermo, resonating with the legacies of Norman, Greek, and Baroque cultures, to the towering presence of Mt. Etna, Europe's highest active volcano, our itinerary is your compass to the hidden gems of this Mediterranean jewel.
Along this voyage, here are three highlights that await:
- Lipari's Vibrant Streets. The heartbeat of the Aeolian Islands, where markets buzz and panoramas leave you spellbound.
- Stromboli's Fiery Majesty. An awe-inspiring spectacle as the volcano offers nature's most dramatic performances.
- Salina's Elixir. The sweet allure of Malvasia wine, a testament to the island's fertile volcanic soils. Every recommendation, every stop, has been vetted through personal voyages and the wisdom of island natives. This is Sicily and the Aeolians as they are meant to be experienced: raw, genuine, and utterly captivating.
So, are you ready to embark on a journey like no other? Dive into our curated Sicily and Aeolian sailing itinerary and make every nautical mile count.
Our Guide To A Sicily Sailing Itinerary
Sicily is often associated with the movie "The Godfather", but we are dedicated to helping you see this wonderful island beyond the classic movie. If you have already been in other parts of Italy, you will definitely understand that Sicily is a unique experience. We are very excited to embark on our Sicily sailing itinerary with you and explore many majestic architectural buildings and catacombs as well as breath-taking landscapes. This trip is designed to move at a good pace but still gives you the perfect mix of fun activities and free time, and incredible cuisine, of course.
We can't claim that you could possibly see everything Sicily has to offer, but you will enjoy the formidable Mt. Etna to the colourful markets in Palermo on this Sicily sailing itinerary.
- Getting There Portorosa Marina which is the starting point of our Sicily sailing itinerary can be easily accessed via a taxi from either Catania Airport (78 miles) which is served by major airlines with flights from all over Europe and further afield, or from Palermo Airport (131 miles), which is the ending point of our Sicily sailing itinerary.
- Mooring For mooring on ourSicily sailing itinerary, you will find plenty of options, with many marinas and safe anchorages. In Vulcanom we recommend anchoring in Porto di Ponente. This cove will protect you well from the easterly winds. On the next stop, in Filicudi, you can drop your anchor in Punta La Zotta, another safe bay. In Salina, you will find moorings in the town port. With 160 berths for boats and yachts up to 210 meters long, Santa Marina Salina is a nice mid-size port - however, in the July and August, we recommend booking in advance. On Stromboli, you won’t find any moorings in the port, but if you go to the west side of the harbor, you will find a great anchorage with water and fuel replenishment offered. There is also an anchorage in Ginostra, where you can moor for a fee. The water is quite deep at 100-1000 meters deep so take care to let the anchor rode down enough.
- Weather Sicily has a Mediterranean climate, with arm dry summers and cool rainy winters. In the summer temperatures on average range from 30 degrees celsius to a low of 23 degrees celsius, making it the perfect time to complete our Sicily sailing itinerary in the warm dry weather.
Sicily Sailing Itinerary
Day by day
- Day 1
Day 1
Portorosa
Portorosa
Start the week off in magnificent Portorosa, where you can enjoy some sunshine on the beaches of Sicily. The town of Tonnarella is close by and offers plenty of ways to pass the day. If you like being active, you can explore Mount Etna, this volcanic mountain is beloved by hikers and history buffs alike.
Recommended Restaurants and Activites:
- Ristorante Pizzeria La Conchiglia dal 1977, Via Camparia, 70, 98054 Furnari ME, Italy
- Day 2
Day 2
Portorosa → Vulcano 20NM
Vulcano
For day 2 of our Sicily sailing itinerary, head to Vulcano. Here you’ll find beautiful hot springs, where you can relax and enjoy the natural therapeutic mud. Afterwards your skin will feel smooth and soft, like never before.
Vulcano is home to Fossa di Vulcano, which gives the island beautiful black sand beaches. You can spend the day snorkeling and swimming. Take the hour-long hike up, and you’ll be rewarded with a view of a crater encrusted by red and yellow crystals.
Recommended Restaurants and Activities:
- Salita al Cratere Museum - Strada Provinciale 179, 98055 Lipari ME, Italy
- Malvasia Pane Cunzatu & Restauran - Via degli Eucaliptus, 98050 Vulcano Porto ME, Italy
- Day 3
Day 3
Vulcano → Filicudi 23 NM
Filicudi
In Filicudi, you can experience truly wild beauty. Escape everyday life on this remote island, filled with nature. You can walk the ancient prehistoric pathways all across the island. Paved with multi-coloured flowers, capers, vines, and olive trees, you’ll see Filicudi’s countryside. Visit Capo Graziano or Zucco Grande, to see what remains of the island’s prehistoric villages. You can also sail to see La Canna, a rock that sticks out of the ocean, where you might be able to spot an elusive Eleanora’s Falcon.
Recommended Restaurants and Activities:
- Grotte del Bue Marino, Dorgali, 08022 Dorgali NU, Italy
- Pensione Ristorante La Sirena, Località Pecorini a mare, 98050 Filicudi ME, Italy
- Day 4
Day 4
Filicudi → Salina 14 NM
Salina
Day 4 of Sicily sailing itinerary brings you to Salina. As the second-largest island of the Aeolian Islands, Salina is also one of the most mountainous areas. Here you will find three of the area’s highest points, Monte Fossa dell Felci (962m), Monte dei Porri (860m), and Monte Rivi (850m). There is also unique and beautiful foliage, and you can enjoy being amongst lush greenery accompanied by freshwater springs. You can also explore three villages and some smaller hiking hills. At the end of the day, enjoy a lovely sunset in Pollara!
Recommended Restaurants and Activities:
- Rinella Harbour, 98050 Province of Messina
- Pizzeria da Marco, Via Rotabile, 18, 98050 Leni - Rinella ME, Italy
- Day 5
Day 5
Salina → Stromboli 22NM
Stromboli
Next, sail on to Stromboli. You’re back in the Mount Etna’s domain and you can spend the day hiking and exploring any parts you did not see the first time. Stromboli also has the elegant black sand beaches from the volcanic ash - you can even see the lava streaming to the water.
You can also explore the town of Ginostra, where the cannoli is authentically delicious and, the blend of Neapolitan and Sicilian influences make for an amazing gastro-experience.
Recommended Restaurants and Activities:
- Trattoria Ai Geckos, Via Salina, 12, 98050 Stromboli ME, Italy
- Punta dei Corvi Lookout, Ginostra, 98050 Lipari ME, Italy
- Day 6
Day 6
Stromboli → Lipari 25 NM
Lipari
On day 6 of the Sicily sailing itinerary, you will pass by Panarea, the smallest island Aeolian Islands on our itinerary. You can hike the Punta del Corno for an amazing view, or enjoy the port town.
The main event of the day is the island of Lipari. Lipari, much bigger than Panarea, is the largest and oldest Aeolian Islands. This is where we recommend you restock as larger supermarkets are available here. To learn more about the island’s deep history, visit the Aeolian Museum in the town. You’ll be able to see the island’s ancient artefacts. Lipari is also home to a 13th-century cathedral, which is home to well-preserved Norman style architecture.
Recommended Restaurants and Activities:
- Swimming and Snorkelling on the island of Basiluzzo, Northeast of Lipari, Italy
- Castello di Lipari, Castello di Lipari, 98050 Lipari ME, Italy
- Day 7
Day 7
Lipari → Portorosa 22 NM
Portorosa
On the last day of our Sicily sailing itinerary, you will make the trek back to Portorosa. If you’d like a leisurely sail back, you can stop into the Vulcano National Park, or sail to the Milazzo Peninsula. You will need to return your boat and check out by the end of the day, but stay and enjoy the wonderful ambience in Portorosa.
Recommended Restaurants and Activities:
- Ritrovo Manuja Restaurant, Contrada Cannotta, 17, 98050 Vigliatore ME, Italy
Got A Burning Question About Sicily Sailing Itinerary?
Where charters went
Past trips from Aeolian gateway: Portorosa, Capo d'Orlando and Milazzo can help you weigh up where to sail.
Where trips from Aeolian gateway: Portorosa, Capo d'Orlando and Milazzo went
- 1 Cala Junco 61
- 2 Porto di Levante 61
- 3 Santa Marina Salina 55
- 4 Stromboli Porto 50
- 5 Pecorini a mare 25
- 6 Pignataro 25
- 7 Yacht Lipari 22
- 8 Cala Bianca 21
- 9 Lipari Portosalvo 16
- 10 Vulcano Gelso 14
2026 season to 4 October (not finished).
Destination groups
Furthest from base
The furthest point reached on each trip, measured in a straight line from base in nautical miles. This is not the distance sailed.
Most common first night out
- Porto di Levante
- Vulcano Gelso
- San Salvatore
Most common last night before return
- Porto di Levante
- Pignataro
- Pecorini a mare
How we worked this out
Boats at sea broadcast their position through AIS, a ship-tracking system. We combine the overnight stops of many charter boats based in Aeolian gateway: Portorosa, Capo d'Orlando and Milazzo, so the figures describe the whole area and never one boat. Distances are measured in a straight line from base.
Aggregated AIS ship-tracking data for the sailing area. No individual boat is shown, and these patterns do not predict future routes.
Past trips from Palermo can help you weigh up where to sail.
Where trips from Palermo went
- 1 Cala Dogana* 50
- 2 San Vito lo Capo* 33
- 3 Calamoni* 33
- 4 Finocchio Marino* 25
- 5 Conca* 17
- 6 Ustica* 17
- 7 Cala Manione* 17
- 8 Cala Trapanisa* 17
- 9 La Caletta* 17
- 10 Trapani* 17
* Marked places have limited evidence. Their figures may change as more trips are recorded.
2026 season to 4 October (not finished).
Destination groups
Furthest from base
The furthest point reached on each trip, measured in a straight line from base in nautical miles. This is not the distance sailed.
How we worked this out
Boats at sea broadcast their position through AIS, a ship-tracking system. We combine the overnight stops of many charter boats based in Palermo, so the figures describe the whole area and never one boat. Distances are measured in a straight line from base.
Aggregated AIS ship-tracking data for the sailing area. No individual boat is shown, and these patterns do not predict future routes.
Past trips from West Sicily: Marsala, Trapani and the Egadi can help you weigh up where to sail.
Where trips from West Sicily: Marsala, Trapani and the Egadi went
- 1 Calamoni* 79
- 2 Finocchio Marino 55
- 3 San Vito lo Capo* 48
- 4 Cala Dogana 45
- 5 Cala Rossa 41
- 6 Baia del Preveto 21
- 7 Porticciolo di Levanzo 19
- 8 Cala Graziosa* 19
- 9 Cala Azzurra* 10
- 10 Cala Monaci* 10
* Marked places have limited evidence. Their figures may change as more trips are recorded.
2026 season to 4 October (not finished).
Destination groups
Furthest from base
The furthest point reached on each trip, measured in a straight line from base in nautical miles. This is not the distance sailed.
Most common first night out
- San Vito lo Capo
- Cala Dogana
Most common last night before return
- San Vito lo Capo
- Calamoni
- Porticciolo di Levanzo
How we worked this out
Boats at sea broadcast their position through AIS, a ship-tracking system. We combine the overnight stops of many charter boats based in West Sicily: Marsala, Trapani and the Egadi, so the figures describe the whole area and never one boat. Distances are measured in a straight line from base.
Aggregated AIS ship-tracking data for the sailing area. No individual boat is shown, and these patterns do not predict future routes.
Ready to book your 7 Day Sicily Sailing Itinerary to the Aeolian Islands?
Independent, award-winning yacht charter advice since 2011. We'll match the perfect boat and crew to your Italy sailing dates — every quote tailored, every detail handled.
Founding member IFCYA · Independent advisory since 2011