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Yacht sailing holidays & skippered tours in Italy

Discover more than 179 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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4.8

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

August - September

Starting from

€1,875

€1,219

Per person

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Maddalena and South Corsica aboard a Catamaran with Hostess

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€1,890

€1,512

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,190

€990

Per person

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4.7

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

Italy: Tuscany

6 days - 5 nights

4 departures available

August

Starting from

€750

€638

Per person

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4.6

Cruise to the Maddalena Archipelago and South Corsica

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

August - September

Starting from

€785

€667

Per person

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5.0

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

5 departures available

August

Starting from

€200

€170

Per person

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

Italy: Tuscany

6 days - 5 nights

3 departures available

August - September

Starting from

€1,000

€850

Per person

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Eco Mini-Cruise on the West Coast of Sicily

Italy: Sicily

2 days - 2 nights

2 departures available

August

Starting from

€500

€450

Per person

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4.8

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August

Starting from

€910

€819

Per person - min 2 pax

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4.3

Sardinia by sailing: from Asinara to La Maddalena and Strait of Bonifacio

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August - September

€800

€720

Per person

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Sailing Cruise - The Odyssey - Egadi Islands - Sicily

Italy: Aegadian islands

6 days - 6 nights

2 departures available

August

Starting from

€950

€855

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Italy: Tuscany

7 days - 6 nights

5 departures available

August - September

Starting from

€700

€630

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

12226 reviews

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A day on a sailing boat to Gallinara Island or the Dianese Gulf

05/21/2025

Roberta N.

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Italy

Bellissima giornata nelle acque liguri, Matteo skipper professionale e simpatico ha insegnato a me ed alla mia amica le basi del veleggiare ottimo l’aperitivo, peccato nn aver visto i delfini sarà x la prossima uscita 😊
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A day on a sailing boat to Gallinara Island or the Dianese Gulf

05/20/2025

Sabrina L.

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Italy

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Weekend of relaxation and fun from Genoa

05/20/2025

Patrizia S.

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Italy

Bella ed interessante esperienza! Mauro lo skipper disponibile e attento agli ospiti. Alcuni posti li avevo visitati in passato ma visti dal mare hanno un fascino particolare.
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A day sailing in the fantastic Gulf of Trieste

05/20/2025

dino m.

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Italy

Giornata splendida per il tipo di esperienza, per l’ambiente e per la preparazione dello skipper che è stato ottimo anche per tutte le informazioni su quel tratto di costa che ci ha fornito. Molto preparato.. Persona gentile e cordiale, Ci siamo divertiti. Esperienza da ripetere!!

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