Portorosa, Sicily Sailing Itinerary
Charter a yacht from our Portorosa base, unfurl your sails in the shimmering Mediterranean and weave between a string of sensational Aeolian Islands. Use our Aeolian islands sailing itinerary to help you make the most of this mystical land of volcanoes, sea caves and black sand beaches.
Flotilla itineraries
Enjoy relaxed sailing grounds and consistent winds on one of our flotilla charters in the Aeolian Islands. Cast off from our base Portorosa and explore Italy’s most desirable coastlines as you dine on magnificent cuisine. Soak up Italian culture whilst making your way around volcanic islands on a week-long adventure along the Sicilian coast and Aeolian Islands.
Choose Itinerary
7 Day Portorosa Bareboat Itinerary
Set sail from Portorosa and explore the full chain of Aeolian islands. The cruising grounds blend chic ports of call such as Panarea Island, with the quiet ambience of islands off the tourist track such as Salina. Explore the imposing volcanoes, abundant castles and historic waterfront villages.
Highlights
- Relaxed sailing with consistent winds and volcanic islands
- Clear, warm waters ideal for snorkelling
- Spectacular black sand beaches
- Europe’s second largest active volcano
- Short passages between Aeolian islands
Day 1
Portorosa – Portorosa
Our newest Italian base, Portorosa is nestled into the north east corner of Sicily, sheltered under the gaze of the majestic Mount Etna. Spend your first day exploring the town of Tonnarella, or reclining on one of Sicily’s many beaches. Chart briefings run between 6pm and 7pm local time, and you will also be given a thorough yacht briefing on your first afternoon.
Mooring
Mooring fees not included.
Day 2
Portorosa to Vulcano
Named for the steaming peaks that crown this fair island, Vulcano is actually better known for the therapeutic qualities of the local mud and the natural hot springs. Although it has a harsh, barren terrain, the island also boasts a black sand beach and the spectacular Fossa di Vulcano. The smoldering crater is encrusted with vivid red and yellow crystals, which makes the one-hour hike well worth the effort. You can then either take a steep path down to the crater floor or walk on the level around the rim and enjoy extraordinary views out over the islands to the north. There is even a volcano museum on the island. The south and northwest coasts are ideal for snorkeling and swimming. Anchor in Porto di Ponente for good protection from prevailing easterly winds.
The day’s sailing
- 1.5 Hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.
Mooring
Mooring fees not included.
Day 3
Vulcano to Filicudi
Filicudi is the wildest and most beautiful Aeolian Island, with its stunning Blue Grotto and a network of hiking trails allowing visitors to explore the island’s scenic interior. The Scoglio della Canna (Cane Reef), a rock obelisk located off the north-western coast, is also worth a visit. At Capo Graziano, a short walk south-east of the port, are found the remains of a prehistoric village, dated 1800 BC. Hiking trails across the Island are spread over a huge network, leading to the abandoned village of Zucco Grande and to Fossa Felci, a mountain in the centre of the Island.
The day’s sailing
- 4.5 Hr Sailing time
- 23 Nautical miles
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Day 4
Filicudi to Salina
Renowned for its vibrant plant life and lush vegetation rare for such volcanic land, Salina has three of the highest peaks in the area, as well as three villages and a handful of smaller hamlets. The abundant greenery is supported by the numerous freshwater springs. Embrace the slower pace of life on the island and rent a bike or scooter to explore Salina and her mighty peaks, Monte Fossa dell Felci (962m); Monte dei Porri (860m); and Monte Rivi (850m). Once at the top, you’ll revel in sensational views that stretch across the entire Aeolian archipelago. Salina has good amenities, and several restaurants line the waterfront in Santa Marina Salina, with seafood dishes a real highlight.
The day’s sailing
- 3 Hr Sailing time
- 14 Nautical miles
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Mooring
Mooring fees not included.
Day 5
Salina to Filicudi
After anchoring for lunch at Pollara, the next island on our itinerary is Filicudi which is among the prettiest and least-developed island in the Aeolian archipelago. Characterised by stunning blue grottos and prehistoric villages, flotilla guests will grab a mooring buoy and settle in for dinner and overnight stay.
The day’s sailing
- 2.5 Hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Mooring
Mooring fees not included.
Things to do
Sunbathing, Snorkelling, Diving, Shopping, Exploring
Facilities
Restaurants, Provisioning, Bike hire
Day 6
Stromboli to Lipari
Stop off in Panarea, the smallest but by far the most picturesque of the islands in the group. Or visit the island of Basiluzzo, close to Panerea, which is uninhabited and an ideal stop off for swimming, snorkelling and fishing. Lipari is both the largest and oldest of the Aeolian Islands, which are often named in its honour. The Aeolian Museum in Lipari Town is excellent and houses treasures from the islands throughout the ages. Lipari is the most populated of the Aeolian Islands, with its population concentrated on the eastern side of the island, where the vineyards produce some really good local wine, and about half living in Lipari Town.
The day’s sailing
- 5 Hr Sailing time
- 25 Nautical miles
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Mooring
Mooring fees not included.
Day 7
Lipari to Portorosa
On our return journey to Portorosa, we will anchor near the southern end of Lipari to admire the island’s towering cliffs and volcanic rock formations known as Faraglioni di Lipari. Afterwards, we sail onwards to Portorosa to enjoy our final farewell dinner together.
The day’s sailing
- 4.5 Hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
7 Day Portorosa Flotilla Itinerary – Italian Cuisine
Discover the best of Italy and create memories that last a lifetime with SailEatalia’s Italian Cuisine Portorosa Flotilla. Depart from our base in Portorosa Marina, and set sail on a magnificent adventure along the Sicilian Coast and Aeolian Islands to explore some of Italy’s best local cuisine. Each Italian region has its own local food and delicacies, so you can expect truly authentic, traditional food in every island that you visit. SailEATtalia’s Italian cuisine Portorosa flotilla will ensure you have the support and assistance of a lead yacht with professional crew on board. There is a chance that the flotilla route may be changed due to weather conditions or particular/unforeseen events.*
**Sail, eat and drink your way around Italy’s stunning Aeolian Islands as an add-on to your yacht charter for an additional €495 per person, which includes some dinners.
*We will do our utmost to accommodate all the listed stops. However, please be aware that routes may change due to weather conditions or availability.
Highlights
- Relaxed sailing and stunning volcanic islands
- Spectacular black sand beaches
- Group dinners
- Clear, warm waters ideal for snorkeling
- Europe’s second largest active volcano
2026 departure dates:
06-06 | 27-06 | 29-08 | 12-09
To book a SailEATailia flotilla, call 888 350 3568
Day 1
Portorosa
Begin your flotilla charter with a warm welcome and refreshing libation at the lovely Portorosa Marina, nestled in the northeast corner of Sicily. Spend the first day getting familiar with your yacht and getting to know fellow travelers at the base before reclining on one of Sicily’s many beaches or exploring the nearby town of Tonnarella. Sleep on board your yacht and wake up to your morning flotilla yacht briefing.
The day’s sailing
- 0 Hr Sailing time
- 0 Nautical miles
To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.
*We will do our utmost to accommodate all the listed stops. However, please be aware that routes may change due to weather conditions or availability.
Things to do
Sunbathing, Snorkelling, Diving, Shopping, Exploring
Discover Portorosa
Tonnarella
Explore the charming town of Tonnarella and sample world-renowned Sicilian cuisine. Relax on lovely sandy beaches that stretch along either side of the beautiful harbour.
Day 2
Portorosa – Volcano
Set sail towards the other-worldly island of Vulcano, named for the steaming peaks that crown the island. You’ll anchor in Porto di Levente or Ponente Bay for good protection from easterly winds. Vulcano boasts a spectacular black sand beach, but its star attraction is Fossa di Vulcano. This fascinating smoldering crater is crystal-encrusted and features epic views once you’ve reached the peak. Vulcano’s south and northwest coasts are ideal for snorkeling and swimming. After a day of exploring, tempt your palate with mouth-watering seafood and local wines at a restaurant near the port.
The day’s sailing
- 3 Hr Sailing time
- 15 Nautical miles
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Day 3
Volcano – Panarea
Leaving Vulcano’s unique landscapes, we will stop at the beautiful and stylish island of Panarea. If you would prefer a longer stretch of sailing, you are welcome to sail to Stomboli. Discover the island’s black sand beaches, or spend the afternoon at the small village of Ginostra, where an interesting blend of Neapolitan and Sicilian sweet delicacies meet rural Sicilian countryside.
The day’s sailing
- 5 Hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Mooring
Anchoring options
Things to do
Sunbathing, Snorkelling, Diving, Shopping, Exploring
Facilities
Water, Taxi, Shower, Rubbish, Restaurants, Provisioning, Bars, Electricity, Ice, Gift Shop
Day 4
Panarea -Salina
Next, you’ll set off for Selena, an island renowned for its lush green mountains and freshwater springs. Embrace the island’s slower pace of life and opt for exploring its mighty peaks (Monte Fossa delle Felci, Monte dei Porri, and Monte Rivi) at your leisure. The group will moor overnight in the island’s port and end the day’s adventures with a group dinner at a local restaurant, where local seafood dishes are sure to satisfy after a splendid day of exploring.
The day’s sailing
- 11 Nautical miles
- 2 hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Mooring
Anchoring options
Mooring fees not included.
Things to do
Sunbathing, Snorkelling, Diving, Shopping, Exploring
Facilities
Water, Taxi, Showers/ Toilets, Rubbish, Restaurants, Provisioning, Bars, Electricity, Ice, Gift shop
Discover Selena
Rinella
Movie buffs can pay a visit to Rinella, located on the south end of the island. Rinella’s small harbour is set in a picturesque bay that provided the scenic backdrop in the Italian movie “Il Postino “.
Sunset in Pollara
If there is time, visit Pollara on the northwest coast and unwind with beautiful sunset views overlooking the small islands of Allicudi and Filicudi.
Day 5
Salina to Filicudi
After anchoring for lunch at Pollara, the next island on our itinerary is Filicudi which is among the prettiest and least-developed island in the Aeolian archipelago. Characterised by stunning blue grottos and prehistoric villages, flotilla guests will grab a mooring buoy and settle in for dinner and overnight stay.
The day’s sailing
- 2.5 Hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Mooring
Mooring fees not included.
Things to do
Sunbathing, Snorkelling, Diving, Shopping, Exploring
Facilities
Restaurants, Provisioning, Bike hire
Day 6
Filicudi – Lipari
Heading towards the largest Aeolian Island of Lipari, we will anchor at the famous white pumice beach “spiaggia Bianca di pomici” before docking in marina Lunga for the night. In the evening, we will join together for dinner in a traditional agriturismo.
The day’s sailing
- 3.5 Hr Sailing time
- 16 Nautical miles
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Day 7
Lipari to Portorosa
On our return journey to Portorosa, we will anchor near the southern end of Lipari to admire the island’s towering cliffs and volcanic rock formations known as Faraglioni di Lipari. Afterwards, we sail onwards to Portorosa to enjoy our final farewell dinner together.
The day’s sailing
- 4.5 Hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Day 8
Portorosa
Begin your flotilla charter with a warm welcome and refreshing libation at the lovely Portorosa Marina, nestled in the northeast corner of Sicily. Spend the first day getting familiar with your yacht and getting to know fellow travelers at the base before reclining on one of Sicily’s many beaches or exploring the nearby town of Tonnarella. Sleep on board your yacht and wake up to your morning flotilla yacht briefing.
The day’s sailing
- 0 Hr Sailing time
- 0 Nautical miles
To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.
*We will do our utmost to accommodate all the listed stops. However, please be aware that routes may change due to weather conditions or availability.
Things to do
Sunbathing, Snorkelling, Diving, Shopping, Exploring
Discover Portorosa
Tonnarella
Explore the charming town of Tonnarella and sample world-renowned Sicilian cuisine. Relax on lovely sandy beaches that stretch along either side of the beautiful harbour.
7 Day Aeolian Islands Flotilla Itinerary
Discover Italy’s most desirable coastlines and create refreshing life-long memories on an Aeolian Islands flotilla vacation in Portorosa. Among the shimmering warm waters of the Mediterranean, cast off and explore together as you weave between a labyrinth of sensational volcanic islands. Enjoy relaxed sailing with consistent winds and short passages from one remarkable UNESCO-protected location to the next. With black sand beaches and authentic Sicilian culture beckoning on shore, your flotilla lead crew will lend support during every step of your nautical journey.
*We will do our utmost to accommodate all the listed stops. However, please be aware that routes may change due to weather conditions or availability.
Highlights
- Relaxed sailing with fine winds
- Clear, warm waters ideal for snorkelling
- Spectacular black sand beaches
- Europe’s second-largest active volcano
- UNESCO-protected Aeolian Islands
2026 departure dates:
23-05 | 20-06 | 11-07 | 19-09
To book an Aeolian Islands Flotilla, call 888 350 3568.
*The program may be changed due to weather conditions or particular/unforeseen events.
**The cost of participation is €295 per person, which includes lead yacht, assistance, fuel, welcome drink and happy hour. Cost of yacht, mooring fees and restaurants are not included.
Day 1
Portorosa
Begin your flotilla charter with a warm welcome and refreshing libation at the lovely Portorosa Marina, nestled in the northeast corner of Sicily. Spend the first day getting familiar with your yacht and getting to know fellow travelers at the base before reclining on one of Sicily’s many beaches or exploring the nearby town of Tonnarella. Sleep on board your yacht and wake up to your morning flotilla yacht briefing.
The day’s sailing
- 0 Hr Sailing time
- 0 Nautical miles
To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.
*We will do our utmost to accommodate all the listed stops. However, please be aware that routes may change due to weather conditions or availability.
Things to do
Sunbathing, Snorkelling, Diving, Shopping, Exploring
Discover Portorosa
Tonnarella
Explore the charming town of Tonnarella and sample world-renowned Sicilian cuisine. Relax on lovely sandy beaches that stretch along either side of the beautiful harbour.
Day 2
Portorosa to Vulcano
Named for the steaming peaks that crown this fair island, Vulcano is actually better known for the therapeutic qualities of the local mud and the natural hot springs. Although it has a harsh, barren terrain, the island also boasts a black sand beach and the spectacular Fossa di Vulcano. The smoldering crater is encrusted with vivid red and yellow crystals, which makes the one-hour hike well worth the effort. You can then either take a steep path down to the crater floor or walk on the level around the rim and enjoy extraordinary views out over the islands to the north. There is even a volcano museum on the island. The south and northwest coasts are ideal for snorkeling and swimming. Anchor in Porto di Ponente for good protection from prevailing easterly winds.
The day’s sailing
- 1.5 Hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.
Mooring
Mooring fees not included.
Day 3
Volcano – Panarea
Leaving Vulcano’s unique landscapes, we will stop at the beautiful and stylish island of Panarea. If you would prefer a longer stretch of sailing, you are welcome to sail to Stomboli. Discover the island’s black sand beaches, or spend the afternoon at the small village of Ginostra, where an interesting blend of Neapolitan and Sicilian sweet delicacies meet rural Sicilian countryside.
The day’s sailing
- 5 Hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Mooring
Anchoring options
Things to do
Sunbathing, Snorkelling, Diving, Shopping, Exploring
Facilities
Water, Taxi, Shower, Rubbish, Restaurants, Provisioning, Bars, Electricity, Ice, Gift Shop
Day 4
Panarea to Salina
Moving on from Panarea or Stromboli, we sail towards the tiny islet of Basiluzzo, the smallest of the eight Aeolian islands, for a day stop with stunning scenery. Later we sail to Salina, with its lush green mountains and freshwater springs, where we’ll end the day with dinner at a local restaurant.
- 2 hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.
Mooring
None
Things to do
Sunbathing, Snorkelling, Diving, Shopping, Exploring
Facilities
Water, Provisioning,Bike hire, Electricity, Fuel
Day 5
Selena – Filicudi
Next on our itinerary is Filicudi, the wildest and most beautiful Aeolian Island, characterized by its stunning blue grottos and a network of hiking trails. Flotilla guests have the opportunity to explore the Scoglio della Canna (Cane Reef), a rock obelisk located off the northwestern coast. At Capo Graziano, a short walk southeast of the port, discover the remains of a prehistoric village, dated 1800 BC. Hiking trails allow visitors to explore the island’s scenic interior and lead to the abandoned village of Zucco Grande and to Fossa Felci, a mountain in the center of the island.
The day’s sailing
- 2 Hr Sailing time
- 11 Nautical miles
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Mooring
Mooring fees not included.
Things to do
Sunbathing, Snorkelling, Diving, Shopping, Exploring
Facilities
Provisioning, Bike hire, Electricity, Fuel
Discover Filicudi
The Grotta del Bue Marino
Consider exploring the Grotta del Bue Marino, a huge sea cave on the west coast of Filicudi. You’ll marvel in the scale and depth of its natural wonder as the afternoon sun’s rays reflect off the water and transform the cave into a dazzling cobalt blue grotto.
La Canna & Punta Zotta
A natural basalt finger rising from the sea, the La Canna rock formation is home to the rare Eleonora’s falcon. An excellent place to snorkel, you can drop anchor in the bay of Punta La Zotta before heading to the rock.
Day 6
Filicudi to Lipari
Next, we set course for Lipari, both the largest and oldest of the Aeolian Islands. You’ll moor overnight in the Port of Lipari. Enjoy an aperitif then stroll picturesque streets along the harbour’s lively seafront.
The day’s sailing
- 3.5 Hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Things to do
Sunbathing, Snorkelling, Diving, Shopping, Exploring
Facilities
Restaurants, Provisioning, Bike hire
Discover Lipari
Aeolian Museum
The Aeolian Museum in Lipari Town is excellent and houses treasures from the islands throughout the ages.
Day 7
Lipari to Portorosa
On our return journey to Portorosa, we will anchor near the southern end of Lipari to admire the island’s towering cliffs and volcanic rock formations known as Faraglioni di Lipari. Afterwards, we sail onwards to Portorosa to enjoy our final farewell dinner together.
The day’s sailing
- 4.5 Hr Sailing time
To be used as a guide only. Based on suggested sailing lanes and average wind speed for area.
Step Aboard Here
Start your experience with Sunsail on land and sign up to receive e-mails from us about yachts, offers and destinations.
By clicking 'Sign up' you confirm that you have read and understood our Privacy Policy and consent to our use of your information.