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Private yacht sailing holidays with skipper in the Aeolian Islands

Private yacht sailing holidays with skipper in the Aeolian Islands

Discover the magic of sailing holidays in the Aeolian Islands! Hire a whole boat: a new way of traveling with your loved one, your friends or your family. Find your dream adventure among thousands of holidays from the Mediterranean to the Caribbeans.

  • Sailing Holidays
  • Italy
  • Aeolian Islands
  • Whole boat with skipper

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • AEOLIAN ISLANDS: sea, sun and relaxation - Brand new 15-metre Lagoon 50 Catamaran

    from 1 April - 7 nights
    Aeolian Islands Italy
    4 people interested
    in this holiday
    651€ Per person
  • 47 reviews

    Easter by boat to discover the Aeolian Islands

    from 6 April - 4 nights
    Aeolian Islands Italy
    Join in on this experience!
    393€ Per person
  • 16 reviews

    Sailing excursion to the Aeolian Islands

    from 6 April - 3 nights
    Aeolian Islands Italy
    Join in on this experience!
    227€ Per person
  • 4 reviews
    almost
    confirmed

    Aeolian Islands on a sailing boat - Easter and Easter Monday

    from 8 April - 6 nights
    Aeolian Islands Italy
    Join in on this experience!
    624 571€ Per person
  • AEOLIAN ISLANDS: sea, sun and relaxation - Brand new 15-metre Lagoon 50 Catamaran

    from 8 April - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    651€ Per person
  • 49 reviews
    2 discounted
    spots

    Aeolian Islands in Blue between sea and sky: Sun, sport, music, good food ... The rest is magic!

    from 8 April - 6 nights
    Aeolian Islands Italy
    3 people interested
    in this holiday
    636 593€ Per person
  • 16 reviews

    Sailing excursion to the Aeolian Islands

    from 9 April - 4 nights
    Aeolian Islands Italy
    Join in on this experience!
    318€ Per person
  • 47 reviews

    Sailing Trekking & Mountain Bike to the Aeolian Islands

    from 13 April - 3 nights
    Aeolian Islands Italy
    1 person interested
    in this holiday
    318€ Per person
  • confirmed

    Discovering the Aeolian Islands aboard a Gulet!

    from 15 April - 7 nights
    Aeolian Islands Italy
    1 person interested
    in this holiday
    1.129€ Per person
  • AEOLIAN ISLANDS: sea, sun and relaxation - Brand new 15-metre Lagoon 50 Catamaran

    from 15 April - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    651€ Per person
  • 16 reviews

    Sailing excursion to the Aeolian Islands

    from 16 April - 4 nights
    Aeolian Islands Italy
    Join in on this experience!
    318€ Per person
  • 4 reviews

    Let's discover the Aeolian Islands together by sailing

    from 21 April - 4 nights
    Aeolian Islands Italy
    Join in on this experience!
    358€ Per person
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Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Reviews - Private yacht sailing holidays with skipper in the Aeolian Islands

19 reviews
20 / 10
Ludovico  S.

Ludovico S.

review about Between the Aeolian Islands and Capo Milazzo September 2022

10 / 10
I have taken many sailing holidays, and Antonino is one of the best and nicest skippers I have met. He puts passion, professionalism, has fun and entertains. It was a nice holiday, thank you Antonio from the whole group ????
Chiara M.

Chiara M.

review about Eolian Sailing- Max 4 guest for exclusivity and relax - Hostess on Board August 2022

10 / 10
Thanks to Mark and Adele we spent a wonderful family holiday: Mark, passionate and experienced skipper, made us relive the exciting experience of sailing, Adele always very careful not to miss anything and always ready to play cards with our children! They taught us and told us many things about life on the boat and the islands - we felt really welcomed and comfortable and we hope to repeat soon this experience that has no equal to fully experience the sea!
Livia O.

Livia O.

review about To the Aeolian Islands on a 14 mt with Gabriella -skipper and mum- and Nicola -seaman and companion of adventures- July 2022

10 / 10
The memories from the week spent with Gabriella and Nicola on their boat will stay with us forever! Gabriella is not only a skillful skipper but also a mum who knows how to engage and (when necessary) keep in check children of all ages. Nicola was a great companion for our 2 children, they had great fun together on the boat and on shore! The played board games, snorkelled, dived and fished together. It was beautiful to witness. The places Gabriella suggested for us to visit were spectacular and she always recommended things to do based on our interests and moods. The entire week was planned together with great flexibility on Gabriella's part. We wouldn't hesitate to recommend Gabrilella and Nicola if you are looking for a truly unique experience! Grazie Gabriella e Nicola!
Cristian C.

Cristian C.

review about The ideal holiday among the 7 pearls of the Tyrrhenian Sea in a true unspoiled paradise - Hostess on board July 2021

10 / 10
Our week in the Aeolian Islands with Luigi and Laura exceeded all expectations, we were immediately welcomed as friends and pampered and always listened to as special guests. Luigi has always been very careful to create an itinerary that was comfortable but that adapted to our desires and needs, while Laura always sweetened everything with lunches and snacks and delicious aperitifs and always attentive to our tastes. But obviously the real star is the sweet little dog Tancredi, a real dispenser of pampering and sweetness, the icing on the cake! The week has really flown by, we can say that we have met two special people who have always been attentive and present without ever being intrusive who have brought us with love and passion through some of the most beautiful landscapes in the world.
Sara Z.

Sara Z.

review about “Distinct & Distant” - 3 Cabins and 3 Bathrooms - Recent boat - Expert skipper June 2021

10 / 10
I would absolutely recommend this holiday even for those like us who were at the first experience of this kind. The Aeolian Islands undoubtedly deserve but doing them safely with an experienced skipper like Antonio certainly gives relaxation and peace. Antonio pleasant and nice person gave us some great advice on choosing places to see and restaurants to try. The boat is absolutely comfortable and well maintained, 3 dignified spacious rooms with attached bathroom, it is clean with the pots and pans necessary to prepare meals. I would say that everything went in the best way, an experience of 10 and praise, certainly to be redone.
Daniele F.

Daniele F.

review about September weekend in the Aeolian Islands September 2019

10 / 10
The 2 days aboard Andrea's boat were wonderful for both me and my 7 Norwegian colleagues. Great connoisseur of the Aeolian Islands, he always had a couple of options ready to offer us, depending on the weather conditions and our interests. He never imposed anything on us, satisfying our requests, and still giving us valuable suggestions on the best restaurants or where to find the best granita in the archipelago. On board he was always kind, helpful, chatty and ready to give explanations if something was not clear. He made us coffee for breakfast and even cooked the fish at bbq! In 2 words, Andrea was fundamental x the happy success of our weekend!
Vanessa C.

Vanessa C.

review about Aeolian Islands in freedom and relax May 2019

10 / 10
Great stay, a very attentive and really friendly skipper, very good memories, thank you for everything Mario!
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Top Destinations

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  • Ionian Islands
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  • Saronic Islands and Athens area
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  • Corsica
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Top Travel Ideas

  • Adventure
  • Catamaran
  • Courses & regatta
  • Day trips
  • Flotilla
  • Gulet and sailing ship
  • Monohull
  • Offshore
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  • Whole boat with skipper
  • All inclusive
  • Crewed
  • WWF Sailing Cruises
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