Skip to main content
7 photos

Sailing trip to the Aeolian Islands

A one-way cruise from the Sicilian metropolis of Palermo, which is well worth seeing, via the Aeolian islands of Lipari, Vulcano and Stromboli, the ‘lighthouse of the Mediterranean Sea’, through the Strait of Messina to the ancient cosmopolitan city of Syracuse. A relaxed sailing trip with time for swimming directly from the ship, shore excursions and relaxation in one of our declared favorite areas.

Routenkarte der Segelroute 17
Start / end
Syracuse – Syracuse
Arrival
Catania
Group size
Max. 26 guests
Places
Syracuse - Strait of Messina - Aeolian Islands - Syracuse

Itinerary

Every sailing trip follows the conditions of nature. The itinerary shown is a non-binding orientation and can change depending on wind and weather.

Individual arrival in Syracuse. Optional transfer from Catania airport.

The moment you step aboard CHRONOS, the special way of life on board begins: a stylish ambience, a warm-hearted crew and the relaxed atmosphere of a classic sailing yacht. After the welcome, you enjoy a welcome drink on deck and the first dinner together.

If Aeolus, god of the winds, is favourable, we cast off after breakfast. Should the wind still be resting, we use the morning for an excursion to the archaeological park of Syracuse – with its Greek and Roman theatres and the famous “Ear of Dionysius”, whose acoustics still impress to this day.

In the afternoon, CHRONOS sets sail along Sicily’s east coast. In the background, Etna rises majestically, often with a snow-capped summit. After about five hours, we reach Aci Trezza, the so-called Cyclops Coast. According to legend, the black basalt rocks in the sea are the stones the blinded Polyphemus hurled after Odysseus.

The early morning belongs to Etna. A panoramic road takes us up to an altitude of around 2,000 metres. Solidified lava flows, crater landscapes and surprisingly green vegetation reveal the two faces of this active volcano.

In the afternoon, we continue on to Taormina. The Corso Umberto invites you to stroll, lined with small boutiques and cafés. Particularly impressive is the Greek theatre with its sweeping view of the sea and Etna in the background – a panorama that Goethe is said to have called the “most beautiful balcony in Europe”. An optional detour takes you to the mountain village of Castelmola, perched high above the coast.

Today an impressive day at sea awaits us through the Strait of Messina. The currents are noticeable; here the sea shows itself lively and powerful.

With a little luck, dolphins or larger shoals of fish accompany us on our way north. The view alternates between Sicily and the Italian mainland as CHRONOS sets course for the Aeolian Islands. In the evening, we finally reach this island world of volcanic origin and drop anchor in a sheltered bay near Lipari – surrounded by black cliffs, warm light and absolute peace.

The day begins at a relaxed pace with a visit to the fascinating archaeological museum on the castle hill. Here we delve deep into the island’s history – from prehistoric finds to the famous small terracotta theatre masks that once served as grave goods.

The Romanesque cloister of the cathedral also invites a quiet moment above the rooftops of the town. Afterwards, you are free to wander through the lively old town with its small shops, cafés and typical southern Italian bustle. In the afternoon, CHRONOS crosses over to the neighbouring island of Vulcano – a short hop into an entirely different, almost surreal volcanic landscape.

The morning on Vulcano starts early, before the sun grows too strong. If you like, you can climb the Gran Cratere – an impressive hike up to the rim of a still-active volcano. At the top, a spectacular view opens into the steaming caldera with its fumaroles, the smell of sulphur and an almost lunar landscape. At the same time, you can see across the entire Aeolian archipelago.

In the afternoon, we sail on to Stromboli. The constantly active volcano is visible from afar. As dusk falls, Stromboli puts on its famous show: glowing eruptions of lava that light up the sky again and again – a natural phenomenon that seafarers have called the “Lighthouse of the Mediterranean” for centuries.

We enjoy dinner on board at a safe distance from the Sciara del Fuoco, while the volcano flares up at regular intervals in the background – an unforgettable moment between tranquillity and the raw power of nature.

At sunrise, we pass through the Strait of Messina once again. The currents carry us on our way back south as Sicily slowly comes into view again. Especially impressive is the view of Etna, often wrapped in clouds as it keeps watch over the coast.

In the afternoon, we arrive back in Syracuse. Here the Captain’s Dinner marks the festive finale of the voyage – either at anchor in a quiet bay or in atmospheric style on the town quay of the Ortygia peninsula.

After breakfast on deck, it is time to say goodbye to CHRONOS and the island world around Sicily. A last look at the sea, the coast and memories of volcanoes, ancient cities and tranquil bays accompany you on the transfer back to the airport. If you wish, you can extend your stay ashore.

Your sailing yacht

CHRONOS

With its 54 m length and 1000 m² sail area, our CHRONOS is without doubt one of the most beautiful and fast large luxury sailing yachts. “Your sailing boutique hotel!”

CHRONOS

Cabin equipment

  • Wardrobe
  • Hairdryer
  • Hand and bath towels
  • Air conditioning
  • 230 V sockets
  • Life jackets
Discover the yacht

Deluxe cabin

Approx. 12–13 m², single or double beds, bathroom with washbasin & WC, shower cubicle (70 × 90 cm).

Long cabin

Approx. 11 m², double bed (2.10 × 1.60 m), bathroom with washbasin & WC, shower cubicle (70 × 90 cm).

KAIROS

Our first ship — and with her this special sailing concept was founded in 2007. At 38 m long with 556 m² of sail area, KAIRÓS is a little smaller than CHRONOS and RHEA, which makes her all the more personal and lets guests lend a hand on deck.

KAIROS

Cabin equipment

  • Wardrobe
  • Hairdryer
  • Hand and bath towels
  • Air conditioning
  • 230 V sockets
  • Life jackets
Discover the yacht

Cabin A

The largest cabins on the KAIRÓS, with a fixed double bed and a spacious bathroom.

Cabin B

With bunk beds or a small double bed. Bathroom with WC and a classic yacht shower.

Included services

  • Accommodation on board in the booked cabin category
  • Nautical crew and service on board
  • Sea passage during the trip
  • Full board on board
  • Water sports from on board
  • Water, tea and filter coffee

Not included

  • Travel to and from the yacht
  • Transfers
  • Soft drinks, Nespresso and alcoholic drinks
  • One evening to explore the local cuisine ashore
  • Shore excursions and tips

Dates & prices

Sailing trip from Syracuse to the Aeolian Islands

 – 

Syracuse – Syracuse

Sailing yacht trip

Yacht: CHRONOS

Spots still available
Deluxe cabin (p.p.)
€ 5.400,–
Long cabin (p.p.)
€ 5.200,–
Cabin A (p.p.)
—
Cabin B (p.p.)
—
Request now

Sailing trip to the Aeolian Islands

 – 

Syracuse – Syracuse

Sailing yacht trip

Yacht: CHRONOS

Spots still available
Deluxe cabin (p.p.)
€ 5.400,–
Long cabin (p.p.)
€ 5.200,–
Cabin A (p.p.)
—
Cabin B (p.p.)
—
Request now

Island hopping in the Aeolian Islands

 – 

Syracuse – Syracuse

Culture trip

Yacht: CHRONOS

Spots still available
Deluxe cabin (p.p.)
€ 4.550,–
Long cabin (p.p.)
€ 4.450,–
Cabin A (p.p.)
—
Cabin B (p.p.)
—
Request now

Sailing trip to the Aeolian Islands

 – 

Syracuse – Syracuse

Sailing yacht trip

Yacht: KAIROS

Sold out
Deluxe cabin (p.p.)
—
Long cabin (p.p.)
—
Cabin A (p.p.)
€ 3.700,–
Cabin B (p.p.)
€ 3.300,–

Sailing trip to the Aeolian Islands

 – 

Syracuse – Syracuse

Sailing yacht trip

Yacht: KAIROS

Sold out
Deluxe cabin (p.p.)
—
Long cabin (p.p.)
—
Cabin A (p.p.)
€ 3.700,–
Cabin B (p.p.)
€ 3.300,–

Sailing trip to the Aeolian Islands

 – 

Syracuse – Syracuse

Sailing yacht trip

Yacht: KAIROS

Spots still available
Deluxe cabin (p.p.)
—
Long cabin (p.p.)
—
Cabin A (p.p.)
€ 3.700,–
Cabin B (p.p.)
€ 3.300,–
Request now

Island hopping in the Aeolian Islands

 – 

Syracuse – Syracuse

Sailing yacht trip

Yacht: KAIROS

Spots still available
Deluxe cabin (p.p.)
—
Long cabin (p.p.)
—
Cabin A (p.p.)
€ 3.700,–
Cabin B (p.p.)
€ 3.300,–
Request now

Book now

Send us your request without obligation — we will get back to you personally.

Trip details
Personal information
Additional information
How did you hear about us?

The data sent to us via the form will be stored by us in accordance with our data protection regulations and will not be passed on to third parties under any circumstances.

Fields marked * are required.

Important information

You can travel from major airports and with the usual airlines. If you want to travel in a more climate-friendly way, you can check the options by train or ferry.

The cruise price includes: costs for the nautical crew and service, accommodation on board in the booked category, sea transport, full board on board / one evening per week to discover the local cuisine at your own expense, water, tea, filter coffee. The price does not include: arrival and departure, transfers, soft drinks, Nespresso and alcoholic beverages, water sports from on board, shore excursions and gratuities.

In summer it is (almost) always nice and warm – although it usually remains pleasant on board above the water – in spring and autumn it is cooler, you sometimes need a sweater, and the weather is more changeable than in summer. The winds of the Mediterranean are as diverse as the countries and can be very different depending on the region.

Life on board the Sailing-Classics yachts is very safe and well organised. The vessels meet the highest safety standards and are inspected annually. The captain and helmsman are graduates of a professional maritime college and undergo continuous professional development. The rest of the crew also receive intensive training in how to deal with emergencies. A compulsory safety briefing takes place at the start of every voyage. Furthermore, despite their speed, the yachts sail with remarkable stability – even in heavy weather, hardly any water comes on deck.

Both German and English are spoken on board the Sailing-Classics yachts. The language used amongst the international crew is English, whilst they communicate with guests in both German and English. On the KAIRÓS, we cannot always guarantee communication in German.

Meals on board Sailing-Classics are organised on a full-board basis and are included in the tour price. The day begins with a generous breakfast buffet, followed by a light two-course lunch and coffee and cake in the afternoon. In the evening, the on-board chef prepares a three-course dinner. On the final evening, the festive Captain’s Dinner is the culinary highlight. Once a week, a dinner is held ashore to sample the regional cuisine – this is not included in the tour price. Special dietary requirements and allergies can be catered for if notified in advance.

Sailing-Classics organises shore excursions using the crew’s motorised dinghies. On request, the crew will take you ashore and collect you again free of charge – simply let the team know in good time. In addition, in many sailing areas, the crew organises guided shore excursions with a local guide or accompanied by a crew member. The price per participant is communicated in advance and charged to your on-board account. Of course, you are also welcome to explore the surrounding area on your own.

The cabins on board the Sailing-Classics yachts are comfortable and practically furnished. Each cabin has its own en-suite bathroom with a toilet and shower cubicle, individually controlled air conditioning, a wardrobe, a hairdryer, and hand and bath towels. 230-volt sockets are available for charging electronic devices. A reusable water bottle is provided in every cabin and can be refilled at the water dispenser in the saloon.

At Sailing-Classics, you’re warmly invited to get actively involved in sailing – no prior experience or sailing licence required. You can help set and trim the sails, take the helm yourself, or lend a hand with other tasks on deck. The crew will be happy to explain the basics of sailing to you, show you how radar navigation works on the bridge, or give you a tour of the engine room. Those who prefer to relax can simply enjoy the passing scenery – the motto is: ‘Everything is possible, nothing is compulsory.’

To cancel your sailing holiday with Sailing-Classics, please send your cancellation request by email to info@sailing-classics.com. Written notification is required so that the cancellation can be processed officially. Depending on when the cancellation is made, Sailing-Classics’ tiered cancellation terms and conditions will apply. We strongly recommend that you take out travel cancellation insurance to protect yourself financially.
On-board ABC – everything you need to know

Related trips

Crossing from Valencia to Gibraltar

Crossing from Valencia to Gibraltar. An exciting area with beautiful sailing stages along the Spanish coast into the Strait of Gibraltar.Keep your eyes open - whales can often be seen here! Read more

From € 1.400,– per person

Delivery through the Mediterranean

For sailors - a delivery voyage from Malaga to Malta. The aim is to move the yacht from one region to another. Sailing also takes place at night; shore excursions and swimming stops are not planned. Guests can help with setting and… Read more

From € 1.900,– per person

Sailing trip along the Algarve

Experience an impressive coastal passage along the sunny Algarve to the lively port city of Málaga. This sailing trip combines spectacular nature and relaxed life on board. On board the stylish CHRONOS, you start in Portimão and sail along… Read more

From € 3.200,– per person