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Yacht sailing holidays & skippered tours in Italy

Discover more than 87 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

87

experiences

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4.5

In the blue of Capri and the infinity of the Amalfi Coast

Duration:

2 days - 2 nights

Italy:

Naples & Amalfi Coast

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66 travellers

Starting from

€248

€275

Per person

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Women's sailing

Duration:

2 days - 1 night

Italy:

Tuscany

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5 travellers

Starting from

€177

€197

Per person

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Experience in the Egadi Islands: A Dream on a Sailing Boat

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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16 travellers

Starting from

€360

€400

Per person

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4.9

Week of sea, nature and fun in the Egadi Islands!

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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6 travellers

Starting from

€621

€690

Per person

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5.0

Long weekend among the queens of the archipelago - Elba and Capraia

Duration:

4 days - 3 nights

Italy:

Tuscany

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109 travellers

Starting from

€409

€430

Per person

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4.6

Long weekend of whale watching with WWF guide between Liguria and the French Riviera

Duration:

3 days - 3 nights

Italy:

Liguria

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3 travellers

€419

€441

Per person

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4.9

Relaxation and fun mini-cruise from Genoa to Sanremo

Duration:

4 days - 4 nights

Italy:

Liguria

Give this experience a try!

€418

€440

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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21 travellers

Starting from

€475

€500

Per person

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4.8

Enjoy: in the blue painted blue of the Aeolian Islands

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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141 travellers

Starting from

€504

€530

Per person

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4.6

Long weekend of whale watching with WWF guide between Golfo Paradiso and Gulf of Tigullio

Duration:

3 days - 3 nights

Italy:

Liguria

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18 travellers

Starting from

€389

€409

Per person

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4.5

The most beautiful corners of Sardinia on a Catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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10 travellers

Starting from

€950

€1,000

Per person

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4.0

The hidden jewels of the Aeolian Islands sailing from Palermo

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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39 travellers

Starting from

€451

€475

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 - Yacht sailing holidays & skippered tours in Italy

12218 reviews

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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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1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

05/6/2025

aleksandra w.

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United States

Wonderful experience . Riccardo is a great host and an excellent cook ! The most importantly he is an expert captain with tons of sailing experience and teaching skills ! I highly recommend for solo travelers .

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