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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

3 days sailing among the hidden gems of Palermo - All inclusive & flexible dates

Italy: Sicily

3 days - 2 nights

4 departures available

October

€315

Per person

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4.0

Three days at the Squid Festival in Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

November

€560

Per person

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4.4

Premium

SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

23 departures available

May - October

Starting from

€1,525

€1,373

Per person - min 2 pax

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New

A tour of the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

2 departures available

May

€450

€405

Per person

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4.1

June 2nd long weekend towards Elba and Capraia between bays, sailing and freedom

Italy: Tuscany

5 days - 5 nights

One departure available

May - June

€540

€486

Per person

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New

Gulf of Poets: Shared Sunset Tour by Catamaran

Italy: Liguria

1 day - 0 nights

25 departures available

October

€120

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas with the solar eclipse

Italy: Pantelleria and Lampedusa

6 days - 7 nights

One departure available

July - August

Starting from

€1,299

€1,169

Per person

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5.0

Long live the legendary Squid Festival in Capraia!

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€290

Per person

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4.8

LET'S GO TO TOTANI - Festival in Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€375

Per person

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New

Celebrate a day sailing along the coast

Italy: Lazio

1 day - 0 nights

17 departures available

October

Starting from

€167

Per person

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5.0

A wonderful day.... sul Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

2 departures available

October

€99

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

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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

15128 reviews

Sailing, swimming and aperitif at sunset ... What else?

10/3/2026

Victoire D.

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FR

Perfect afternoon with Emanuele! Wonderful host, generous food and drink and the boat is beautiful and welcoming Many thanks!!

Sailing, sun and sea in the Tuscan Archipelago

10/3/2026

Luca P.

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IT

Overall the experience was positive: it was my first time on a sailing boat and I was left with a great desire to repeat a trip of this type, especially thanks to the good harmony that was created with the group. However, there were some organizational and management aspects that deserve room for improvement: Management and navigation: Claudio is a very nice person, but a more precise planning of the itinerary would have made the difference. By not booking ports in advance, last-minute searches often proved fruitless. In addition, we almost always sailed by motor instead of sailing (used only on two occasions), which is a bit of a shame for a holiday of this type. Movements on land: On the days at anchor near the ports there was little availability in the use of the tender to take us ashore; fortunately we were able to remedy this thanks to the support of a more experienced travel companion. Itinerary: Unfortunately we were unable to reach either Capraia or the Island of Giglio. The adverse weather certainly complicated things, but probably with a different management of the stops at least one of the two stages could have been reached. Boat: The boat itself was beautiful, but in my opinion not suitable for comfortably accommodating 8 people. Also worth mentioning is a small plumbing problem in one of the bathrooms (the backflow of water after draining). Overall an adventure that I would gladly do again, with the hope that these details can be taken as ideas for improvement.
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Aeolian Islands on a catamaran, professional skipper/hostess, what else?

10/1/2026

Federica P.

A fantastic week!!

Sailing in the magical Sardinia of the South

09/30/2026

Moreno B.

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IT

The skippers Gianluca and Valeria are very prepared and professional, also good sailing instructors, nice and good cooks, a detail that should not be underestimated. A good friendship was immediately established. The itinerary to south-east Sardinia made us visit unforgettable bays and sea. I intend to have the same experience next year, perhaps on the west side.

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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 (25)Liguria (7)Northern Sardinia (5)Pontine Islands (4)Sicily (3)Lake Garda (3)Aeolian Islands (3)Naples & Amalfi Coast (2)Southern Sardinia (2)Pantelleria and Lampedusa (2)

Italy: departures by month

november (7)december (3)january (1)february (1)march (1)april (3)may (7)june (6)july (7)august (4)

Other travel ideas

Sailboat (100)Whole boat with skipper (91)Cooking service onboard (43)Catamaran (35)Exotic destinations (28)All inclusive (28)Courses & regatta (12)Offshore (10)Day trips (6)Sport & wellness (5)

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