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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!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

June - September

Starting from

€700

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

July - October

Starting from

€590

Per person

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4.6

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

14 departures available

June - November

Starting from

€1,640

€1,558

Per person - min 2 pax

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

6 departures available

July - October

Starting from

€950

Per person

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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,260

€1,070

Per person

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4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€390

€351

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

9 departures available

June - September

Starting from

€600

€570

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - September

Starting from

€795

Per person

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4.6

Long weekend between Ponza and Palmarola: adventure at the Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

Per person

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4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

3 departures available

June - September

Starting from

€950

€855

Per person

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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

June - October

Starting from

€690

Per person

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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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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

13985 reviews

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Midweek relaxing in the Pontine Islands

06/25/2026

marcella c.

-

IT

Great experience. Very good skipper from all points of view, always ready to add his experience and knowledge. New and well maintained boat.
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Long weekend between Elba and Capraia, from Thursday to Sunday

06/25/2026

Nicola A.

-

IT

Really great experience. The boat is as it appears in the photos, no strange or unpleasant surprises. The places visited were lovely and the experience really great. Victor accompanied us on this trip, instead of Paolo, and he was a really great skipper, very helpful, company and very easy-going. Very very recommended

Short Week at the Egadi Islands between Nature, Relaxation and Fun

06/25/2026

RICCARDO D.

-

IT

An experience that to define excellent would be an understatement. The sailing experience was splendid, with wonderful views, crystal clear sea and the priceless feeling of freedom. But what made this experience truly unique was the human factor. The skipper proved to be an exceptional person in every respect: professional, prepared, attentive to safety, impeccable in organization and endowed with rare relational qualities. He managed to create an atmosphere of serenity, conviviality and sharing that made everyone feel at ease from the first moment, transforming a simple trip into an authentic and memorable experience. The cuisine deserves a special mention. Although meals are not a due or obvious service in this type of experience, the skipper wanted to offer much more than could be expected. And what a surprise! These were not simple meals, but real gastronomic moments. Each dish was prepared with care, passion and great attention to the quality of the ingredients. Honestly, the meals were beyond all expectations: delicious, tasty, irresistible. The kind you look forward to and that, jokingly, can be addictive. Each course was a confirmation of the talent and generosity of the skipper, who also proved to be exceptional in the kitchen, managing to constantly amaze everyone on board. In a world where we often limit ourselves to providing the expected service, here we clearly perceive the desire to offer much more: passion, attention, hospitality and a genuine care for the well-being of guests. It was not only a fantastic sailing experience, but an extraordinary human experience made up of sea, friendship, professionalism and unforgettable flavors. Five stars are not enough. An experience that I would recommend without any hesitation and that I will take with me as one of the best memories of recent years. Congratulations to the skipper: exceptional at sea, exceptional with people and exceptional also in the kitchen.⭐⭐⭐⭐⭐+∞.
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North Sardinia and South Corsica by catamaran with flybridge

06/25/2026

Federica P.

-

IT

First boat holiday... Definitely experience to be redone! The comfortable and spacious bali catspace catamaran with all the comforts. Captain Andriy was the best skipper we could wish for: kind, knowledgeable and safe :)

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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 (100)Aeolian Islands (59)Northern Sardinia (45)Pontine Islands (34)Liguria (28)Aegadian islands (27)Naples & Amalfi Coast (17)Southern Sardinia (16)Sicily (13)Lake Garda (5)

Italy: departures by month

july (234)august (217)september (151)october (41)november (5)december (2)january (1)february (1)march (1)april (1)

Other travel ideas

Sailboat (545)Whole boat with skipper (426)Cooking service onboard (119)Catamaran (95)All inclusive (52)Exotic destinations (28)Family sailing cruises (28)Courses & regatta (27)Day trips (21)Offshore (21)

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