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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

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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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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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

Per person

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5.0

Super!

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - September

Starting from

€550

€495

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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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August - September

Starting from

€850

Per person

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4.9

Super!

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

Italy: Aegadian islands

7 days - 7 nights

2 departures available

August - September

Starting from

€600

€540

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

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4.9

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

Italy: Tuscany

7 days - 6 nights

3 departures available

August - September

Starting from

€650

Per person

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4.8

Super!

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

6 days - 7 nights

2 departures available

September

Starting from

€1,050

Per person

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4.8

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€750

€675

Per person

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4.6

North Sardinia and South Corsica by catamaran with flybridge

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August - September

Starting from

€1,290

€1,190

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

14422 reviews

Week end in Costa Azzurra

08/8/2026

Alina S.

-

IT

Beautiful experience! The owner of the boat is generous and nice. I state that it was my first time of such a stay on the boat, so being part was difficult for me at times (sway effect), but despite this Alessandro did not make us weigh this and spoiled us by treating us as real guests of honor. Thank you for your patience and hospitality. I recommend this type of experience to everyone to experience the sea 100%, especially those who are sea addicted like me🩵
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Aeolian Islands: between sea and authentic flavours

08/8/2026

Irene S.

-

IT

Carlo was a fantastic skipper: attentive, professional and passionate. He guided us between the islands with confidence and passion, making us experience for the first time the beautiful feeling of turning off the engine and sailing! Always ready to answer our thousand questions about boating with infinite patience, and then how can we not mention that delicious calamarata, prepared with fish caught right among the boats? One of the best memories of this experience. Life on a boat is all about shared spaces, collaboration and small compromises, but waking up to the sound of the waves and falling asleep under a sky full of stars is worth it all. It is an experience that we recommend to everyone. Unfortunately, due to the weather and strong winds, we were unable to see two of the planned islands. It will definitely be a good excuse to come back!

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

08/7/2026

Carlotta T.

-

IT

We spent unforgettable days. Great company, lots of aperitifs, beautiful landscapes and a special thanks goes to Livio who made us sail safely, involved in the management of the boat teaching us the tricks of the trade and pampered us with his delicacies!
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Two days at the Marine Protected Area of the Tremiti Islands

08/7/2026

Gioia F.

-

BE

Great experience on all fronts. Marco was an attentive, fun skipper and always ready to pass on his knowledge and passion for the sea and the Tremiti Islands. Wonderful holiday. Super recommended.

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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 (64)Aeolian Islands (36)Northern Sardinia (27)Liguria (22)Pontine Islands (22)Aegadian islands (16)Naples & Amalfi Coast (11)Sicily (9)Southern Sardinia (9)Lake Garda (4)

Italy: departures by month

september (142)october (48)november (5)december (1)january (1)february (1)march (1)april (1)june (1)july (1)

Other travel ideas

Sailboat (335)Whole boat with skipper (285)Cooking service onboard (90)Catamaran (71)All inclusive (46)Exotic destinations (24)Courses & regatta (20)Sport & wellness (17)Day trips (16)Family sailing cruises (15)

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