One Way: The Sicilian coast between the Egadi and Aeolian Islands

Italy:

Sicily

Duration:

5 days - 6 nights

Max number of passengers:

10 people

Available:

July

Boarding from:

Trapani

What's included

Cancellation policy

Organised by:

Giovanni & Matteo

Member since 2021 -

Organisation

Italian

English

This experience, in a nutshell

We set sail from Trapani with only one idea: to let ourselves be guided. No fixed stages, no scripts—the route is written by the wind and the color of the water, between sudden roadsteads, quiet bays and stretches of coastline that change face with every mile.

It is not just a collection of coves: the pleasure also lies in the navigation, in the time when the boat takes off, the sails work and the land moves away just enough to really feel on the road. Sicily always remains there, present and distant at the same time: golden cliffs, the scent of Mediterranean scrub, villages that appear as mirages and sunsets that seem to light up from the sea. You live on dives, silences and small stops when it happens, without haste, following your instinct.

It is a one-way journey: you go on until the dark and volcanic islands appear on the horizon, and Lipari becomes the natural landing place. And when you arrive, you understand that the real destination was the path: the adventure of being carried away.

NB: There is nothing fixed or established, the itinerary will be established at the time of departure and during the navigation according to the weather and sea conditions. The skipper's decisions in this regard will be final. To follow an itinerary for example.

€640

Per person

What's included

Cancellation policy

€640

5 days - 6 nights

Italy: 5 days - 6 nights

Sicily

What's included

Cancellation policy

€640

Show all

Boat & Classes of Service

Beneteau Cyclades 50.5 - 2007

Type

Sailboat

Length

15.5 m.

Toilets

Cabins

16+

Show all

Our itinerary

Our trip starts here:

Trapani.

Check-in: 6:00 PM

Our trip ends here:

Lipari Harbour.

Check-out: 8:00 AM

Leg 1

SATURDAY - Trapani

Boarding from 18:00 at the port of Trapani. Welcome drink, on-board briefing and accommodation in the cabins. Free time for the galley and for a walk in the historic center. Dinner on your own and overnight in port.

Leg 2

SUNDAY - San Vito Lo Capo

First sail to Macari / Santa Margherita Bay: swim in transparent waters and lunch at anchor. In the afternoon arrival in San Vito Lo Capo: walk in the village and sunset on Monte Monaco.

Leg 3

MONDAY - Scopello

Coastal route to the Zingaro Reserve: swimming stops in front of the most beautiful coves, Cala Mazzo di Sciacca - Tonnarella dell'Uzzo area. In the afternoon Scopello and / or Castellammare del Golfo. Night in the sheltered roadstead or in port (depending on weather and places).

Leg 4

TUESDAY - Mondello/Palermo

Navigation to Palermo with a swimming stop in front of Mondello or under Capo Gallo. Arrival in the port in the afternoon, street food and evening tour between the historic center and the marina.

Leg 5

WEDNESDAY - Cefalù

Relaxed sailing towards Cefalù: swim in front of the promontory and afternoon between the Duomo and alleys. Night at anchor or in port

Leg 6

THURSDAY - Filicudi/Vulcano

A day of real sailing: we give up early and head decisively towards the Aeolian Islands. Depending on the weather we will understand whether to head for Filicudi or Vulcano.

The choice between the two destinations will be anything but simple: a breathtaking sunset awaits us in Filicudi , one of those that turn off all thoughts and only light up the sea. In Vulcano, on the other hand, we could enjoy an equally spectacular sunset and then end with a barbecue and/or a final party on land, to say goodbye to the journey properly.

Leg 7

FRIDAY - Lipari

Short navigation to Lipari to spend the day in a couple of magical coves, last swims and finally a small navigation to return to port. Dinner all together in the village.

Leg 8

SATURDAY - Lipari

Breakfast and disembarkation by 8:30 am. Final greetings and goodbye with a baggage full of emotions and new friends.

The itinerary may be subject to changes due to weather conditions and/or technical or logistical reasons, in order to ensure safety and a pleasant sailing experience for all participants.

Leg 1

SATURDAY - Trapani

Leg 2

SUNDAY - San Vito Lo Capo

First sail to Macari / Santa Margherita Bay: swim in transparent waters and lunch at anchor. In the afternoon arrival in San Vito Lo Capo: walk in the village and sunset on Monte Monaco.

Leg 3

MONDAY - Scopello

Leg 4

TUESDAY - Mondello/Palermo

Leg 5

WEDNESDAY - Cefalù

Relaxed sailing towards Cefalù: swim in front of the promontory and afternoon between the Duomo and alleys. Night at anchor or in port

Leg 6

THURSDAY - Filicudi/Vulcano

A day of real sailing: we give up early and head decisively towards the Aeolian Islands. Depending on the weather we will understand whether to head for Filicudi or Vulcano.

Leg 7

FRIDAY - Lipari

Short navigation to Lipari to spend the day in a couple of magical coves, last swims and finally a small navigation to return to port. Dinner all together in the village.

Leg 8

SATURDAY - Lipari

Breakfast and disembarkation by 8:30 am. Final greetings and goodbye with a baggage full of emotions and new friends.

The itinerary may be subject to changes due to weather conditions and/or technical or logistical reasons, in order to ensure safety and a pleasant sailing experience for all participants.

What's included in the price

Boat equipment and facilities

Final cleaning

Tender and outboard

Meals and beverages

Purchase and storage of the galley

Onboard staff

Skipper

Sailor

Taxes, fees and moorings

Embarkation and disembarkation mooring fees

Other services

Trainer

What you'll have to pay during the experience

Below are the additional expenses you will incur during the experience.

Common Fund

€80 - €250 Per person

Galley

Food for the skipper

Food for the crew

Alcoholic drinks

Mooring fees

Visitor or navigation taxes

Access and/or stay in parks and marine protected areas

Fuel (boat/tender)

Starter Pack

€90 Per person

The Starter Pack will be paid for at the time of boarding.

Bedding kit

Towels kit

Association/Membership card

What's NOT included in the price

Below are the services that are not included in the price of the experience, including any available optional services that you may pay directly to the organiser (we advise you to inform the organiser prior to departure in case you wish to purchase such services and arrange the payment terms directly with him).

Excluded

Meals/drinks consumed ashore

The organiser reviews

Organised by:

Giovanni & Matteo

Member since 2021 -

Organisation

Italian

English

4.6/5

out of

reviews

Skipper

Boat

Destination

ENJOY: in the blue painted blue of the Aeolian Islands

09/2/2025

Marino O.

Italy

Would you do a sailing holiday again? Well this is the question that I am repeating to myself already during my first experience and to this day it continues to spin in my head, despite my feet on the ground. Yes and no! Here's the answer! Of course, it was my first experience and honestly if I had to think of approaching the organization of a boat holiday, as it was, I would certainly opt for something else. I really love clarity, especially of costs, transparency and empathy in all those technical-organizational aspects that must be preventive rather than in itinere, which leave no alternative but to ruin and make the traveler uncomfortable even before setting sail. I can say that I had a nice motor trip on a sailboat that was born with considerable sailing potential (according to the experts), but that I was able to appreciate only for a couple of hours out of seven days despite the fact that many other boats were sailing around me. I found insistent indications of frequent ashore descents for dinners and parties even though the group wanted to remain gathered in friendship and sobriety on the boat. Rules are rules and in certain environments they must be respected but in common certain moments for example "galley" which I have heard of as one of the most "exclusive and fun", but which I found and lived with heaviness and frustration. But beyond all this, the group has made a common front and this sense of sharing lived in a small living space, which makes everything amplified, has brought souls together in an incredible unity of purpose. So will I go back to choosing a sailing holiday? I don't know yet, certainly if I can I choose the group, the Friends and the places visited.

ENJOY: in the blue painted blue of the Aeolian Islands

09/1/2025

Manuela P.

Italy

The holiday was enjoyable thanks to our well-established crew of friends, new people added who were meant to stay in my heart, very friendly and helpful staff members, and lovely places seen. Unfortunately, I have to give a negative evaluation to the skippers/organizers who, despite having high qualifications and having been informed several times of the kind of holiday appreciated by all present (sailing holiday) gave priority to motor navigation more to reach pre-established destinations and restaurants to offer rather than to listen to our needs for freedom from time and space, to sail listening to the sounds of the wind and the sea and to relax in nature. The sails were hoisted only once in the whole week despite the fact that the opportunities had also presented themselves other times to our great disappointment given the beautiful boat we were on!! To fill a now full vase was added the lack of clarity and average values much higher than the costs (fuel and general) which led the holiday in the end to be more expensive than we expected. This will certainly teach us to ask for much more precise and detailed information before booking other trips on sailsquare.

Enjoy: in the blue painted blue of the Aeolian Islands

08/31/2025

Cristina C.

Italy

Very prepared skipper, excellent itinerary, nice group and many beautiful vibes!

ENJOY: in the blue painted blue of the Aeolian Islands

08/31/2025

Eva G.

Germany

I recommend this sailing holiday to those looking above all for authentic human relationships and friendships that can become infinite: from this point of view the experience is truly unforgettable. The staff was friendly and attentive. In our case the skipper did not act as a supplement, but it was not a problem because we were already a group. However, it is essential to have clear expectations. If you want to spend the week sailing mainly in advance, it is advisable to find out well in advance: in my case, I only found out after departure that we would only use the sails for a short moment in a single day. Similarly, I didn't know that the skipper/organization was predominantly aiming to eat at local restaurants or kiosks instead of on board. With this information I would definitely have chosen another option or destination.