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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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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

9 departures available

July - November

Starting from

€500

€425

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

July

€590

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

Per person

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4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

6 departures available

July - October

Starting from

€420

€399

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

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

6 departures available

August - September

Starting from

€850

Per person

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4.8

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September - October

€242

€218

Per person

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5.0

New

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

Italy: Aegadian islands

7 days - 7 nights

6 departures available

June - September

Starting from

€650

€585

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€900

Per person

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5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

8 departures available

July - September

€1,600

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

13953 reviews

Afternoon, aperitif and sunset on Verbano - Lake Maggiore

06/22/2026

daniela m.

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IT

I gave this experience to my husband who had dreamed of steering a sailboat for years and was satisfied! Stefano was super kind and helpful in advising me in the best possible way when and how to book and the experience itself was very nice

Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola

06/22/2026

Angelica C.

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IT

A weekend on a sailing boat in Ponza that was just PERFECT from every point of view 🌊⛵️ I can only congratulate our skipper Matteo, who proved to be not only extremely professional, but also incredibly attentive to every detail. The organization was impeccable: everything was planned with precision, but at the same time with that lightness that makes you feel immediately on vacation, without worries. The boat then... wonderful! Clean, well-kept and super welcoming, you can clearly see how much love and passion are behind it. I felt pampered from start to finish, almost like being in the family and not just like a customer. And the surprises? Truly unforgettable! I had NEVER seen a barbecue on a sailboat: a special lunch, in the middle of the sea, with the scent of the grill... something magical. And as if that were not enough, waking up on Sunday with fresh croissants was the icing on the cake 🥐✨ A gesture that encompasses all the care and attention that the skipper dedicates to his guests. It was an experience that I would do a thousand times over and that I recommend to anyone who wants to experience Ponza in an authentic, relaxing and at the same time special way. Thank you very much for this unforgettable weekend! 💙

All-Inclusive Sailing: Capri, Positano, Amalfi

06/22/2026

Maria Grazia I.

-

IT

They were enchanting days. Natural landscapes and enchanting locations. We filled our eyes with so much beauty, unforgettable baths and sunshine. Alessandro, the skipper, wonderful. With organization and skill he allowed us to make the most of the various days. And finally he prepared some really delicious menus to eat on the boat. To sum up :SUPER☺️
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Weekend on the island of Elba: among dolphins, enchanting bays and relaxation

06/22/2026

Elisa M.

-

IT

Wonderful experience. Beautiful sea accompanied by the Skipper Salvatore who was able to guarantee a good atmosphere, safety in the enjoyment of the experiences. Together with Salvatore we were also accompanied by his wife Elisabetta, an empathetic and intelligent woman who increased the pleasantness of the experience! See you next time

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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 (106)Aeolian Islands (59)Northern Sardinia (45)Pontine Islands (39)Liguria (28)Aegadian islands (27)Naples & Amalfi Coast (17)Southern Sardinia (15)Sicily (11)Tremiti Islands (6)

Italy: departures by month

july (238)august (217)september (153)october (41)november (5)december (2)january (1)february (1)march (1)april (1)

Other travel ideas

Sailboat (563)Whole boat with skipper (434)Cooking service onboard (123)Catamaran (92)All inclusive (53)Family sailing cruises (29)Courses & regatta (27)Exotic destinations (27)Day trips (21)Offshore (21)

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