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Monohull yacht sailing holidays & tours in Italy

Discover more than 308 opportunities to get on board a Monohull adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

308

experiences

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5.0

Sail with lunch on board

Duration:

1 day - 0 nights

Italy:

Lazio

Be the first one to book!

€89

Per person

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4.9

Sailing and trekking in Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

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+17 travellers

Have booked

€200

Per person

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4.9

Crossing to the northwest: sailing weekend in Sicily

Duration:

3 days - 2 nights

Italy:

Sicily

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+4 travellers

Have booked

Starting from

€300

Per person

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4.9

Weekend on Elba between Sailing and Trekking

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

Starting from

€280

Per person

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4.9

Trekking and sailing weekend on the island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+3 travellers

Have booked

Starting from

€228

€240

Per person

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Sailing day Genoa, Camogli and San Fruttuoso

Duration:

1 day - 0 nights

Italy:

Liguria

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Roberta R.

Has booked

Starting from

€110

Per person

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4.9

Weekend sailing from Imperia

Duration:

2 days - 1 night

Italy:

Liguria

Be the first one to book!

€190

Per person

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W.E Golfo Dei Poeti-Portovenere-Rosse-Ferale

Duration:

2 days - 2 nights

Italy:

Liguria

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+7 travellers

Have booked

Starting from

€190

Per person

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5.0

Sailing day in the Ligurian nature, boarding from Varazze

Duration:

1 day - 0 nights

Italy:

Liguria

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chiara c.

Has booked

€95

Per person

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5.0

Luxury sailing in the Gulf of Poets

Duration:

1 day - 0 nights

Italy:

Liguria

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Federico G.

Has booked

€90

Per person

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The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

Be the first one to book!

Starting from

€500

Per person

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4.9

Trekking & Sailing Experience-Weekend lungo a Capraia, 2 barche

Duration:

3 days - 3 nights

Italy:

Tuscany

Be the first one to book!

Starting from

€295

€310

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

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 - Monohull yacht sailing holidays & tours in Italy

10001 reviews

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Weekend of sea and colors between Ischia, Procida, Vivara and the Phlegraean fields

10/16/2023

Manuela M.

Quando vuoi avere la certezza di passare un eccellente week and a vela …..non puoi che scegliere Gennaro ed Emilano! Compagni di viaggio ke diventano amici, cibo eccellente preparato con amore dalla ormai carissima Raffaella, richieste improbabili tutte accontentate, barca sempre al top ma soprattutto loro, Gennaro ed Emiliano che fanno la differenza!
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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.

-

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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