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Yacht sailing holidays & skippered tours in Italy

Discover the beauty of Italy and treat yourself to a sailing holiday of relaxation, fun, and unique landscapes. Sail around the beautiful islands of Sicily and Sardinia, discover the Lipari, Pontine and Aegadian Islands by boat or anchor in the romantic bays of Tuscany or Cinque Terres.

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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

13 departures available

July - October

Starting from

€400

€360

Per person

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5.0

Super!

Week on the Costa Smeralda on a full optional catamaran!

Italy: Northern Sardinia

6 days - 6 nights

3 departures available

July - August

Starting from

€1,150

Per person

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5.0

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - November

Starting from

€650

€585

Per person

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5.0

Super!

South Sardinia

Italy: Southern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€790

€751

Per person

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4.7

Dolphins & Whales cruise with WWF guide – Ligurian Sea

Italy: Liguria

5 days - 6 nights

4 departures available

July - September

Starting from

€830

€789

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

7 departures available

August - October

€590

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Italy: Tuscany

7 days - 6 nights

3 departures available

August - September

Starting from

€700

€665

Per person

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4.8

Magical Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€640

Per person

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4.7

Whale watching cruise with WWF guide between Tuscany and Northern Corse

Italy: Tuscany

6 days - 7 nights

7 departures available

July - September

Starting from

€1,041

€989

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

8 departures available

August - 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

11 departures available

July - October

Starting from

€265

Per person

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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€550

€523

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

12520 reviews

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Dream sailing on a fully-equipped catamaran

07/9/2025

Alessandro B.

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Italy

Per noi è stata la prima esperienza in barca e tutte le aspettative sono state soddisfatte! La parte più emozionante è stata aver potuto veleggiare insieme a [hidden]. L’ imbarcazione è in ottime condizioni e l'equipaggio che abbiamo incontrato è stato top. Sicuramente ripeteremo l’esperienza in futuro.
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Escape from the city for a weekend of sea and relaxation

07/9/2025

Monica v.

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Italy

Sono stata con i miei due figlii sulla barca di Carlo nel weekend tra il 4 e il 6 luglio. . La barca è splendida, praticamente nuova, con spazi ampi e confortevoli. Carlo è una persona squisita, socievole ma al tempo stesso discreta, attento alle esigenze degli ospiti. e felice di condividere le sue conoscenze con noi che eravamo alla prima esperienza.. Nonostante le condizioni meteo non fossero eccezionali abbiamo goduto appieno del mare e del vento, avvistato i delfini e dormito anche in rada una notte.. Nota positiva anche per il porto in cui è ormeggiata la barca , che offre servizi eccellenti
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Weekend only four guests - Elba Island

07/9/2025

Paola F.

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Italy

Bellissima esperienza! Pierpaolo skipper super disponibile sia nell’organizzazione sia nello strutturare le varie tappe per farci godere al meglio la barca a vela. Da rifare!
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Sailing weekend in the Pontine Islands

07/9/2025

Antonio F.

-

Italy

Abbiamo vissuto un'esperienza che porteremo nel cuore per molto tempo. Un weekend in barca a vela che è stato molto più di una semplice fuga dalla routine, è stato un tuffo in una dimensione fatta di silenzi, risate, salsedine e libertà. La barca era spaziosa, pulita, curata in ogni dettaglio e organizzata in modo impeccabile, si percepiva l’amore e la professionalità con cui viene gestita. Lo skipper? Straordinario. Presenza discreta ma sempre attenta, ci ha guidati con sicurezza e passione, rendendo ogni momento sereno e autentico. L’organizzazione è stata impeccabile dall’inizio alla fine, senza intoppi, con la sensazione costante di essere in ottime mani. Un’esperienza che consigliamo con il cuore.

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Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

Aeolian Islands

Stromboli, Vulcano and Lipari are just some of the best destinations for a sailing or catamaran vacation in Sardinia.
Guide to the Aeolian Islands on a sailing boat

Sardinia

Costa Smeralda, Maddalena Archipelago and San Pietro Island are just some of the best destinations for a sailing or catamaran holiday in Sardinia.
Guide to the Sardinia on a sailing boat

Capri, Ischia and Procida

Enchanted landscapes and elegant haunts, thermal springs and seabeds full of surprises, simplicity and glamour: there is more than one reason to choose these timeless islands as a destination for a yachting holiday in stages.
Guide to Capri, Ischia and Procida on a sailing boat

Amalfi Coast

Positano, Amalfi and Cetara are just some of the best destinations for a sailing or catamaran holiday in the Gulf of Naples.
Guide to the Amalfi Coast on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
Guide to sailing vacations with children

Italy: the most beautiful places to sail

Italy: departures by month

Other travel ideas

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