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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!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

3 departures available

September

Starting from

€850

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!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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5.0

Super!

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

3 departures available

September

Starting from

€700

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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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

6 departures available

September - October

Starting from

€370

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

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

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4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

5 departures available

September - October

Starting from

€230

Per person

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Get onboard solo, with your family or your friends

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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

14840 reviews

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Cruise in southern Sardinia: charm and turquoise waters in schooner with hostess and full board

08/30/2026

Silvia A.

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IT

Really beautiful gulet holiday, a different experience than usual. We spent days between the sea, beautiful coves, baths, sunsets and lots of relaxation, but also laughter and group moments. The crew was always helpful and kind and contributed a lot to making the holiday enjoyable. The organization was also excellent. The beauty of the gulet is precisely this: for a week you completely disconnect from the routine and experience the sea in a different way, also meeting new people. It was a holiday that I would gladly do again. In fact, I would probably do it again tomorrow!
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Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

08/30/2026

Silvia T.

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IT

Really very nice experience. The boat was comfortable, well maintained and perfectly adequate for the week spent together. Precise and helpful organization, both before departure and during the holiday. A special thanks to our skipper Luca, professional, competent and always attentive, able to manage navigation and life on board with tranquility and discretion, helping to create a pleasant and relaxed atmosphere. A week of sea, sailing, beautiful places and sharing that I will definitely take with me. Experience that I recommend and that I would gladly do again. Fair winds!
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

08/30/2026

giulia b.

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IT

It is challenging to describe an experience, especially when only a few days have passed since its end. I left with my 11-year-old daughter, blindly trusting sailsquare because I had already spent a weekend in the Pontine with the skipper Leonardo and his wife and I was fully satisfied. The Pontine are extraordinary islands from a landscape point of view, for me it is the most interesting sea ever explored with snorkeling, both for the beauty of the marine fauna and for the majesty and variety of the seabed. The company was fundamental, we found true friends, not just travel companions and for this I am grateful. I cannot fail to point out the less pleasant things of the holiday for honesty towards those who organize and those who will use this service in the future. The skipper Antonio is a person of heart, a remarkable cook and an experienced sailor, but his boat is not up to par. It does not have comfortable areas to spend the hours of rest; it is full of details (of no small importance) to be fixed including the limping ladder, the floor that gives way under your feet in some places, the dirt penetrated deeply, the ants. We suffered from the abnormal heat of this period and for this reason we tried to sleep outside (there were 7 of us + the skipper), but alas there were not enough and adequate spaces to find a few hours of peace and rest, to face beautiful but challenging days. In fact, back in port on Friday evening we all disembarked prematurely because we were exhausted by the sleepless nights and exasperated by the discomfort of the external and internal environments. I would not change this adventure, but I would like to leave my sincere comment hoping that it will be interpreted as an incentive to improve by those who have chosen to do this complex and noble job to offer a spartan, but enjoyable stay. In this regard, I would like the boat that has its beauty to be restored, repainted and set up with plenty of cushions (maybe even some backrests where possible would not be bad) so that we can welcome guests as they deserve; the awning is too low on the sides and does not allow you to enjoy the panoramic view and rather than shelter it suffocates; blankets and pads to be used outside should be washed and disinfected every departure, because they give off an unpleasant smell; The engine of the tender should give the guarantee of working, so that the trips are not only beautiful and interesting but also safe. Antonio I know that you care, that the sea is your life and that you know it deeply, so I would like you to welcome my suggestions as an incentive to fill the gaps that penalize your undoubted experience and preparation. I have esteem for you and your wife and I hope that you always have the wind in your sails.

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

08/30/2026

Ferdinando S.

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IT

Great experience The organizational and economic part is adequate and consistent with what is indicated in the program. Boat very well maintained and tidy, Skipper available and very competent, when possible for excellent weather conditions sailing. Very helpful and cooperative travel companions. I suggest the experience to those who have never tried these weeks of vacation.

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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

Italy: departures by month

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