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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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4.8

The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History

Italy: Naples & Amalfi Coast

4 days - 3 nights

One departure available

September

€333

Per person

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4.9

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

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September

€583

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

30 departures available

January - December

Starting from

€300

€270

Per person

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5.0

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

One departure available

August

€390

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€200

Per person

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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€980

Per person

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4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

4 departures available

August - September

Starting from

€850

Per person

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5.0

Super!

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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5.0

Super!

A sailing story between Favignana, Levanzo and Marettimo

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August - September

Starting from

€620

Per person

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5.0

Super!

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

2 departures available

August - September

Starting from

€600

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September

€790

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

Why book a holiday with Sailsquare?

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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

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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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

14518 reviews

Midweek sailing trip: two days at sea in Alassio

08/15/2026

Emanuela P.

Wonderful experience ! To be repeated for sure!
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Egadi Islands, Zingaro Reserve and San Vito Lo Capo

08/15/2026

Sanja J.

It's the third time I've traveled with sailsquare and unfortunately it will also be the last for the following reasons: - elderly skipper (71 years old instead of the 59 shown on the site) with psychomotor slowdown (I am a doctor), who struggled to manage the boat with only the engine, let alone sailing. I remember an episode in which the boat hit a rock and neither the skipper nor the helper (wife) went to check from the outside of the boat if there were any problems and another in which the boat stopped in the middle of the sea due to engine failure that the skipper wanted to manage by towing the sailboat with the dinghy?! We exasperated guests asked for help from a boat that approached asking to call the coast guard, who brought us back to the mainland saving us from 2 clearly good people able to handle the situation. - Unfortunately even Sailsquare instead of helping us find a solution, eg providing us with another boat for the remaining days, offering us a partial refund but above all stopping skipper and helper at least until the situation is clarified, dismissed us by saying that they only act as a conduit for the financial transaction between us and the skipper: SHAME!!

Aeolian Islands in the name of sailing, fishing and relaxation

08/15/2026

Alessandra d.

Antonio was a kind, polite and helpful skipper. We had a wonderful experience that we recommend to everyone and that we will certainly want to repeat!
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Egadi Islands, Zingaro Reserve and San Vito Lo Capo

08/15/2026

David V.

I lost David's place for the cruise. I needed rest. Actual sailing was restricted. When sailing, the boat often proceeded straight ahead without following the wind properly. I called my best friend who is a skipper several times with video calls and was speechless, telling me to leave the boat immediately. In the end, even my friends understood that we could not continue sailing after the boat stopped in the middle of the sea and Mario and Carmen were unable to manage the situation. Mario and Carmen struggle to coordinate with each other in maneuvers, also thanks to Mario's hearing problem, and give each other conflicting instructions. We suggested that they use walkie-talkies that they had purchased specially, but they never used them. The stick used to hook the buoys was lost at sea twice. Carmen was kind to me and tried to speak to me in French. However, Mario and Carmen quarreled with each other over the maneuvers and then the atmosphere was heavy. Mario snores very loudly during the night, significantly disturbing my rest for the duration of the cruise. For me this was a real problem as I needed to sleep and I spent sleepless nights. We found a total lack of flexibility: the one and only request for modification, minimal (stopping in the next bay), was met with disappointment (we were clearly told that they do not operate a "taxi"). On this occasion, we wanted to join friends who were with their catamaran near the beach and had a free buoy next to them. Mario and Carmen chose to moor on the buoy furthest from the beach despite the sea being calm. We were forced to swim about 300 meters without tender assistance, even on the way back late in the evening. Products have been added in particular for the hygiene/cleanliness of Carmen and Mario (about 35-40 €) and food (about 25-30 €) without submitting the list to us before sending. This is unacceptable to me. The worst, however, was the refusal to take us to Levanzo despite the optimal sea conditions, preventing us from visiting one of the three islands of the Egadi then that there are only 3 and we had 7 days of navigation. For me holiday ratées. Florence

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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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