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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!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

2 departures available

August - October

€220

Per person

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5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - October

€690

Per person

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5.0

Super!

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

6 departures available

August - November

Starting from

€500

€348

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

2 departures available

August - September

€1,150

€1,035

Per person

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4.8

Super!

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

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€583

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

30 departures available

January - December

€300

€270

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

Per person

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4.7

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

3 departures available

July - September

Starting from

€360

€324

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

Per person

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4.8

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

August - October

Starting from

€750

€675

Per person

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5.0

Super!

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

6 departures available

August - September

Starting from

€550

€495

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€700

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.

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

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

14329 reviews

Corsica & Capraia - only 4 guests - sun adventure & relaxation!

07/31/2026

David C.

-

DE

An unforgettable holiday in all respects. The skipper is well trained in the area since he has always frequented it, the boat is well maintained and very comfortable. Luca is always available and attentive to everyone's needs and always makes you feel at ease. Even northern Corsica in July does not have many tourists so you can have a quiet holiday and this is not possible elsewhere. Even with the other passengers I was really lucky.
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/30/2026

Valeria M.

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IT

Antonio is a great cook! He cooked great dishes! Very nice! During meals it is nice to listen to his stories. He knows the sea very well, he is attentive and scrupulous. Recommended holiday to experience a week of relaxation in a fabulous sea!

Egadi mon amour: seven days to fall in love, be amazed and relax.

07/30/2026

raffaella s.

-

IT

Giuseppe captain of excellence! He taps his experience and knowledge of the seas he sails, attentive and helpful. He conveys confidence and also a lot of love for his work, his family and for the crew. Listen carefully to all the information and advice he offers you, they are always very useful!! We spent a fantastic week, lulled by crystal clear waters, paradisiacal landscapes and lots of fun. Embark as strangers and disembark as friends!! Don't be surprised if once you get on the ground you are ready to start again: it is the [hidden] effect! Raffaella: if today I dive fearlessly it is thanks to Giuseppe!! Marco: Giuseppe? One of us! Not the Skipper but one of the group Chiara: I brought more seasickness pills than swimsuits, but with Giuseppe at the helm and his tips I didn't use a single one. Great navigation and zero drama! Federico: Giuseppe? A super captain who made me live and appreciate my first boat experience to the fullest. Federica: a huge thank you to Giuseppe for making us live this experience from A to Z... complete with a sailor's shower included in the package. Davide: Giuseppe super Skipper available and always present, he made us spend a wonderful week on a sailing boat. Tiziana: Giuseppe, with his boat [hidden], just like the moon guides you, cradles you, takes you to the stars and the three sister islands

The Island of Elba, to make you live a special experience!

07/30/2026

Giovanna F.

-

IT

Beautiful first experience on a sailing boat, with a skipper attentive to the needs of his guests and scrupulous. Livio, known (for me) as "Lucio", in addition to sailing, with his infinite stories makes you fly to spaces and places of other times ... But be careful not to take away the cookies for breakfast, he could get very angry!! Joke: peaceful and very discreet person. See you soon!

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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 (68)Aeolian Islands (39)Northern Sardinia (31)Pontine Islands (26)Liguria (21)Aegadian islands (18)Naples & Amalfi Coast (15)Southern Sardinia (13)Sicily (11)Lake Garda (4)

Italy: departures by month

august (198)september (145)october (46)november (5)december (1)january (1)february (1)march (1)april (1)june (1)

Other travel ideas

Sailboat (382)Whole boat with skipper (314)Cooking service onboard (98)Catamaran (75)All inclusive (49)Exotic destinations (25)Courses & regatta (19)Family sailing cruises (19)Sport & wellness (18)Day trips (18)

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