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Yacht sailing holidays & skippered tours in Italy

Discover more than 46 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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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

October

Starting from

€200

Per person

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4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October - November

Starting from

€530

€477

Per person

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4.8

Super!

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

2 departures available

October

Starting from

€850

€808

Per person

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4.9

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€751

Per person

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4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

One departure available

September - October

Starting from

€260

€247

Per person

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4.8

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

2 departures available

October

€590

Per person

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4.7

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

October - November

Starting from

€1,455

€1,382

Per person

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4.2

Stuffed anchovies: magical weekend from Genoa

Italy: Liguria

2 days - 2 nights

2 departures available

October

Starting from

€265

Per person

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5.0

Super!

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

Italy: Aegadian islands

7 days - 7 nights

3 departures available

October

Starting from

€400

€360

Per person

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4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

October

Starting from

€294

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

October

Starting from

€615

Per person

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5.0

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

4 departures available

October

Starting from

€337

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

12482 reviews

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On board with the chef at the Egadi Islands

07/6/2025

Loredana R.

-

Italy

La vacanza perfetta ! Sono anni che viaggio con Sailing Square ma mai ho trovato tanta cura ed attenzione . Max è uno skipper attento e preparato . La sua cucina è a dir poco sublime , ti stupisce ad ogni pasto , Vieni svegliato da profumi sublimi ! Ogni giornata è perfettamente organizzata tra bagni in baie protette , gite in barca a Marettimo , veleggiate rilassanti , aperitivi con sottofondo musicale e serate in ristoranti tipici sapientemente suggeriti da Max . La barca è confortevole e con ampi spazi per rilassarsi anche all'ombra grazie ad un grande tendalino .. cosa si può desiderare di più??? Grazie Max
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Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

07/6/2025

Maila L.

Siamo stati a bordo con Matteo e Maria Teresa domenica scorsa ed è stata una giornata bellissima. Una fuga serena e di risate che ci serviva. Veleggiare con il solo rumore del mare e delle risate di nuovi amici è stato il valore aggiunto. La barca è bellissima e tenuta con la cura perfetta dei padroni di casa. Un grazie di cuore per l’accoglienza, l’attenzione ai dettagli e l’empatia. Maila e Davide
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A week in the Aeolian Islands - 6 islands in seven days

07/6/2025

Rosario L.

-

Italy

Capitano e barca al massimo livello. Grande ospitalità , mi sono sentito a mio agio dall' inizio alla fine. Sintonia ottima anche con gli altri passeggeri. Grandi spaghettate ed ottimo cibo a bordo nella cornice delle Eolie che restano fra le migliori destinazioni in Mediterraneo. Capodanno alle Eolie ? speriamo di si.
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Aperitif Trip to the Gulf of Tigullio - All inclusive!

07/6/2025

alice b.

-

Italy

Esperienza veramente favolosa. Super consigliata!

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