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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

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

7 departures available

September - October

Starting from

€230

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September

€950

Per person

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4.8

Super!

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€850

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

4 departures available

August - September

Starting from

€490

Per person

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5.0

Super!

A sailing story between Favignana, Levanzo and Marettimo

Italy: Aegadian islands

7 days - 7 nights

2 departures available

August - September

Starting from

€620

Per person

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4.8

Super!

Vacation between Tuscany and Corsica on a magnificent 17m boat

Italy: Tuscany

6 days - 7 nights

One departure available

August - September

€900

€820

Per person

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5.0

Weekend catamaran in Portovenere and Cinque Terre

Italy: Liguria

3 days - 2 nights

5 departures available

September - October

Starting from

€212

€191

Per person

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4.9

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

3 departures available

August - September

Starting from

€790

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€700

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

2 departures available

August - September

€980

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

September

€400

Per person

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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

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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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

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

14659 reviews

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Maddalena Archipelago, southern Corsica: wonderful Sardinia

08/23/2026

Ambra G.

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IT

A wonderful week, one of those that remind you why sailing is a completely different way of traveling. Massimo gave us excellent navigation and an itinerary designed day by day with great attention, managing to make us discover beautiful places and, which is far from obvious in Sardinia in August, to make us experience them as much as possible away from the crowds. Each choice took into account the sea, the wind and above all the possibility of really enjoying every place, without the feeling of simply having to "tick" stages. We sailed, bathed in incredible waters, ate very well and experienced the boat for what it should be: sea, freedom, sharing and a completely different rhythm from that of every day. A special mention goes to Valentina, a fantastic sailor: very efficient, precise and tireless on board, but above all always present with a delicacy, energy and a smile capable of making the days even more beautiful. And then the crew. Because you can have a beautiful boat, a perfect itinerary and the sea of Sardinia, but when you live 24 hours a day with other people for a week, it is the group that really makes the difference. We were very lucky: we got on board as strangers and we got off inevitably taking home a piece of each other. Massimo is a competent, attentive and deeply sensitive captain, able to read the sea but also the people and the dynamics of the group, leaving everyone their own space. Thank you Captain, thank you Vale and thank you to all our wonderful crew. A trip that I would do again tomorrow.
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Discovering the Argentario on a sailboat

08/23/2026

Paolo P.

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IT

[hidden] is a fantastic boat, very well distributed spaces, well organized, comfort truly remarkable for its length. But the plus was the skippers Arianna and Eleonora who throughout the holiday combined solid nautical skills, enthusiasm in transferring both seafaring and eco and ethological knowledge (especially on cetaceans), depth of thought, authentic sympathy and engaging cheerfulness.
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The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/23/2026

anna maria a.

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CH

Unfortunately very negative experience with sailsquare and with the organization of the day on the boat. We definitely expected more professionalism and attention to the customer, instead we always felt managed at the last moment. The organization was unclear and not very punctual: several things were communicated or managed at the last minute, often leaving us with the feeling of being put in the background. Even the relationship with us was not particularly correct or attentive compared to what we expected.
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Sardinia and Strait of Bonifacio on a 50-foot sailboat

08/23/2026

Arturo P.

-

IT

Positive experience. The skipper knows the locations and the coves well, and always offers excellent solutions. He is also a good cook! Boat kept in good condition.

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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

Tuscany (44)Aeolian Islands (29)Pontine Islands (22)Liguria (19)Northern Sardinia (18)Aegadian islands (12)Naples & Amalfi Coast (9)Southern Sardinia (7)Sicily (5)Lake Garda (4)

Italy: departures by month

september (141)october (50)november (5)december (1)january (1)february (1)march (1)april (2)june (1)july (1)

Other travel ideas

Sailboat (248)Whole boat with skipper (212)Cooking service onboard (76)Catamaran (57)All inclusive (41)Exotic destinations (22)Courses & regatta (16)Offshore (13)Day trips (11)Sport & wellness (11)

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