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ENJOY: in the blue painted blue of the Aeolian Islands

Italy:

Aeolian Islands

Duration:

6 days - 7 nights

Max number of passengers:

10 people

Available:

-

Suitable for travellers:

18 - 55 years

Boarding from:

Lipari

What's included

Cancellation policy

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Organised by:

Giovanni & Matteo

Member since 2021 -

Organisation

Italian

English

This experience, in a nutshell

Sicily is embraced by a sea of infinite shades, rich in history and traditions where art and culture meet and accompany you as you sail through the picturesque islands that surround it.

Crystal clear sea, unspoiled nature, active volcanoes and 6000 years of history have allowed the Aeolian Islands to become a UNESCO World Heritage Site.



The key words of this experience will be Sail & Enjoy... Browse and enjoy! A week dedicated to leisure, sharing and new friendships.


The energy of the volcanoes, the intense blue of the water, the scent of the islands, will surprise and excite you more and more every day.



N.B. The program below is purely indicative and non-binding and may be changed at the sole discretion of the captain, based on sea weather conditions or for reasons of force majeure if they should result in lack of safety for guests, crew and boat. 


No Departures available

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8+

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Boat & Classes of Service

Beneteau Cyclades 50.5 - 2007

Type

Sailboat

Length

15.5 m.

Toilets

3

Cabins

5

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9+

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Our itinerary

Our trip starts here:

Lipari.

Check-in: 6:00 PM

Our trip ends here:

Lipari.

Check-out: 9:00 AM

Leg 1

Saturday - Lipari

Our tour starts from Lipari, where from 18:00 on Saturday you can embark. Once settled in the cabin there will be a short organizational briefing with the skipper and then off to the village to enjoy the first evening all together and to get to know each other better!


Leg 2

Sunday - Panarea (2 HOURS)

On Sunday morning we set off. We will set the bow towards the crystal clear waters of the pumice quarries for a first swim. We will continue the navigation by heading to the island of Panarea, the most chic of the seven sisters. We will make the first anchorage at Cala Zimmari, a perfect bay to venture with mask and fins in its crystal clear water. In the late afternoon we will move in front of the village. As always, there are those who enjoy the sunset waiting to dine under the stars and those who cannot give up visiting the island for a walk through the white alleys surrounded by boutiques, and then find ourselves at the raya, a club and disco, with one of the most beautiful terraces on the island. Here we will enjoy an aperitif on the terrace of the raya, with soft lights, admiring the Stromboli that, restlessly, puffs on the horizon is an experience that alone is worth this trip.


Leg 3

Monday - Stromboli

On Monday morning it will be the turn of Lisca bianca. This anchorage is a must-see stop in the Aeolian Islands, as well as for snorkeling but also for solfatare. After swimming in the sulphurous waters of Panarea, we will head towards Stromboli or IDDU, the most active volcano in Europe, so dear and feared by the islanders, unmistakable for its conical shape and the cloud of black smoke that is almost perpetually stationed on its top. It will be the tongue of black and volcanic beach at the foot of the village of San Vincenzo to host us at anchor to be able to go ashore and to visit the country. Once on land, it will be pleasant to meet on the terrace of the Ingrid Bar for an aperitif together.


Leg 4

Tuesday - Salina

The largest of the islands, with extraordinary beauty and variety of landscapes. The morning and lunch will be dedicated to the eastern part of the island, where we will be able to admire the green seabed and the steep cliffs overlooking the sea of Capo Faro. In the afternoon we will sail to Santa Marina, after a swim we will get ready to visit the town, colored by the flowers of the caper and the typical Aeolian houses, for those who wish, it will be possible to visit one of the many wine cellars of the island. You can return by boat for dinner if you want or for those with a sweet tooth instead it is time to take a trip to Lingua where pane cunzatu and granita da Alfredo are waiting for you!


Leg 5

Wednesday - Filicudi

On Wednesday morning we will sail to Filicudi, but first we will swim in the bay of Pollara made famous by the film The Postman. The beauty of this bay is characterized by a rock formation that creates a natural arch and the small fishermen's deposits carved into the rock. After seeing Pollara, we will continue sailing towards Filicudi and if we are lucky it will also be possible to spot some dolphins or turtles. Capo Graziano will host us for a swim, for those who love snorkeling, here they will have fun. We will then continue to Pecorini a Mare, an agglomeration of fishermen's houses where in the evening the Saloon will be waiting for us, the legendary place that awaits us boaters for its delicious Malvasia accompanied by Sicilian appetizers prepared by the ladies of the village and a cheerful chat under the stars.


Leg 6

Thursday - Vulcano

On Thursday morning, as soon as we wake up, breakfast and head to the west coast of Filicudi to admire La canna (an eruptive rock formation that rises from the sea to a height of about 74 meters above sea level) and the Montenassari rock. After a bath in the bluest bluest possible, we set sail for Vulcano, Baia di Ponente to prepare for an eventful evening in the village for lovers of nightlife or for a nice evening of chatting and company in the tranquility of the protected bay waiting for one of the most evocative sunsets of the Aeolian Islands.


Leg 7

Friday - Lipari

The day of return to Lipari. But the cruise isn't over yet. For those who want, early in the morning is the ideal time to climb the Volcano, or you can take advantage of a tour through the streets of the village and a breakfast with granita and brioche at Remigio's which is always a great satisfaction. Today we will move to the south side of Vulcano, after admiring the  Grotta del Cavallo, here there are two beautiful bays: Baia di Gelso and Baia della spiaggia del Cannitello, also with black sand. In the bay of Cannitello beach, a bar is open for a happy hour or aperitif on the beach accompanied by dancing music. A last swim at sunset in the shadow of the Faraglioni of Lipari, is the worthy conclusion of this wonderful week spent together. Back in port, the cruise is not over yet because we will console ourselves with an excellent dinner all together in one of the best restaurants in Lipari,  to honour this beautiful week spent together in the best possible way.


Leg 8

Saturday - Disembarkation

Disembarkation will take place on Saturday morning by 9:00 am.


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.

Frequent questions

The organiser reviews

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Organised by:

Giovanni & Matteo

Member since 2021 -

Organisation

Italian

English

4.6/5

out of

52

reviews

Skipper

Boat

Destination

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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.
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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.
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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!
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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.

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