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Yacht sailing holidays & skippered tours in Italy

Discover more than 1 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

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Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in Italy

10604 reviews

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

10/16/2023

Damien B.

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Switzerland

It was my first excursion by boat and it was an incredible experience! I can only recommend it! The landscapes are beautiful and the boat is well-maintained with enough space and a nice Skipper. ++ Dario knows a lot about the sea and his boat! He likes to share what he knows about it. He knows also when to integrate the group and when to let things happen. He likes humans and is very kind. During, before and after he was also very reachable. -- I would have appreciated more information and clarity about excursions. I added them below to help the comments readers. ?? Be aware of taking good shoes, warm clothes and a torch if you want to climb the Stromboli (which I highly recommend) There is the possibility of eating in restaurants on different islands. Being barefoot is recommended on the boat. Bring your eco-shampoo with you. The bedsheets were furnished. Hope that's help and that you will enjoy the tour!
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Aeolian Islands in Blue between sea and sky: Sun, sport, music, good food ... The rest is magic!

10/16/2023

Davide P.

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Italy

Bella Vacanza, lo Skipper Dario è molto competente la sua passione per il mare è trasmessa con amore a tutti i membri dell' equipaggio, conosce benissimo le isole e sa come muoversi.
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La Maddalena archipelago: sailing between Budelli, Caprera and Lavezzi

10/15/2023

Jacopo Maria M.

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Italy

Prima volta in barca a vela per me e la mia ragazza Giulia, non possiamo che ringraziare Renato! Grazie a lui abbiamo trascorso una bellissima settimana all'insegna del relax e del divertimento visitando posti fantastici. Grande capitano (e grandissima persona), affidabilissimo e con grande esperienza che sin da subito ci ha messo a nostro agio. Nessun imprevisto e nessun intoppo, tutto come da programma (da leggere con attenzione onde evitare spiacevoli discussioni)! Nonostante il poco vento dove si poteva si aprivano le vele per provare l'emozione. Sicuramente torneremo a viaggiare insieme, grazie Renato!
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A week in the Aeolian islands, six islands in seven days

10/13/2023

Ylenia M.

E' stata una settimana indimenticabile a bordo della Iaia. Anche se ci sono proposte di vacanze con barche più recenti, non fatevi ingannare dall'apparenza. La Iaia ha dei comfort che non sono scontate sulle imbarcazioni e a bordo ti senti veramente a casa. Le Eolie sono una meta che consiglierei a tutti, è una vacanza rilassante che ti porta dalle calette e da paesaggi naturalistici mozzafiato ad assistere all'eruttazione dello Stromboli navigando sotto un cielo stellato. Nicola è un ottimo skipper e di lunga esperienza e ci ha fatto sentire veramente sicuri a bordo con lui. Ha soddisfatto ogni nostra curiosità riguardo al luogo e alla navigazione e ci ha fatto apprezzare il mare sotto un altro punto di vista, quello dell'intimità con il luogo e le sue bellezze, cosa che non si coglie dalla terraferma. Non solo Nicola è una persona veramente piacevole, ma fa anche delle ottime torte :)

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