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Private yacht sailing holidays with skipper in Italy

Chartering a sailing boat in Italy will let you discover a new way of travelling new way of travelling in complete freedom. Choose between a catamaran or a sailing boat and embark with an experienced skipper to discover Tuscany, Sicily, Tuscany, Sicily, Sardinia and many other destinations.

324

experiences

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Maddalena and South Corsica aboard a Catamaran with Hostess

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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9 travellers

€1,512

€1,890

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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64 travellers

€990

€1,190

Per person

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Yoga Retreat on a Catamaran

Duration:

6 days - 6 nights

Italy:

Naples & Amalfi Coast

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Mirta

€1,658

€1,950

Per person

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4.8

Super!

Lampedusa, Lampione e Linosa fra colori magici

Duration:

7 days - 7 nights

Italy:

Pantelleria and Lampedusa

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34 travellers

€595

€700

Per person

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4.7

Two boats walking on the island of Elba: the magic of the roadstead!

Duration:

6 days - 5 nights

Italy:

Tuscany

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Lorena L.

Starting from

€638

€750

Per person

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4.6

Cruise to the Maddalena Archipelago and South Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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30 travellers

Starting from

€667

€785

Per person

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5.0

Poetic Gulf of Poets

Duration:

3 days - 2 nights

Italy:

Liguria

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13 travellers

Starting from

€170

€200

Per person

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4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Duration:

3 days - 3 nights

Italy:

Tuscany

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18 travellers

Starting from

€342

€380

Per person

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4.3

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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4 travellers

Starting from

€720

€800

Per person

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4.8

Super!

Large Luxury Catamaran with Hostess - Discovering the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€1,251

€1,390

Per person

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4.9

From the Pontine to the Egadi Islands - Adventure, Navigation, and Relaxation - One Way

Duration:

6 days - 6 nights

Italy:

Aegadian islands

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2 travellers

€531

€590

Per person

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4.7

1st One-Way Special - Between the island of Elba, Corsica and Sardinia

Duration:

6 days - 6 nights

Italy:

Northern Sardinia

Give this experience a try!

€774

€860

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 - Private yacht sailing holidays with skipper in Italy

1300 reviews

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1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

05/8/2025

Maria Pia D.

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Italy

TOP
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A long weekend of sea and freedom from Argentario to Elba

05/7/2025

RAFFAELE L.

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Italy

Per il ponte del 1 maggio 2025 siamo stati a bordo di OTHELLO per una minicrociera di 4 giorni. La barca è molto bella, elegante ma estremamente funzionale e curata, comoda e con molte dotazioni. I bagni riservati nelle singole cabine sono stati per noi un dettaglio importante, come gli ampi spazi anche all’interno. L’atmosfera da subito è stata accogliente e simpatica grazie ad Enrico che si è dimostrato per tutta la vacanza uno skipper straordinario sia per le sue doti tecniche che come persona. Tonia, la compagna di Enrico, ha completato la splendida atmosfera respirata sulla barca con la sua simpatia, empatia e accoglienza. Il gruppo quindi si è amalgamato in modo molto speciale. Un meteo favorevole ci ha permesso di svolgere il programma previsto: Argentario, isola del Giglio ed Isola D’Elba. Enrico, con la sua esperienza ha organizzato le tratte in modo sicuro, considerando venti e correnti. E’ stato molto bravo a coinvolgerci in tutte le fasi della navigazione, a secondo dei livelli di conoscenza e di interesse individuali. Mia moglie ed io consigliamo vivamente un’esperienza con Enrico e Tonia, che con tutti i loro racconti ci hanno lasciato una grande voglia di tornare su OTHELLO e di visitare tanti altri luoghi.
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Weekend in Capraia, the island with timeless sunsets

05/7/2025

Leonardo R.

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Italy

Marco è un grande appassionato di vela ed un professionista del settore della nautica. Lo capisci subito perché ti coinvolge nel suo mondo sin dal primo minuto e condivide con gli ospiti le sue esperienze e le attività di bordo, sempre e solo in piena sicurezza. Sono stati due giorni divertenti; lo consiglio a chi ha voglia anche di imparare e di rilassarsi allo stesso tempo!
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Weekend in Capraia, the island with timeless sunsets

05/7/2025

Simone S.

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Italy

Un’ottima esperienza, Marco un grande skipper appassionato del mare!

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