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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

Super!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

Starting from

€453

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

One departure available

September

€490

€440

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

One departure available

September

Starting from

€441

€419

Per person

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4.8

Super!

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

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€700

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€200

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

4 departures available

September - October

Starting from

€230

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

4 days - 4 nights

2 departures available

September

Starting from

€490

€440

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

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

One departure available

September

€950

Per person

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5.0

Super!

Midweek Tuscan archipelago

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€500

Per person

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5.0

Super!

Weekend on Elba on a 16-meter sports boat

Italy: Tuscany

2 days - 2 nights

One departure available

September

€400

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

15000 reviews

Midweek getaway between Elba and Capraia

09/11/2026

Samanta B.

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IT

Fantastic experience on board! Edoardo is a competent skipper, a real sea dog who knows how to create a cozy atmosphere on the boat and patiently explained to us how to sail. He also recommended excellent trekking routes in Elba, an extra touch that made the cruise even more special, and the boat was very clean and well cared for
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The magic of the Egadi Islands aboard a brand new catamaran

09/11/2026

Emiliano C.

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IT

Beautiful places, the overwhelming contact of nature, with a pleasant crew and a Giuseppe, an experienced skipper, proactive and decisive.
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Midweek relaxing in the Pontine Islands

09/11/2026

dario r.

-

IT

A simply wonderful experience, one of those that are difficult to forget. We had a wonderful experience in the Pontine Islands aboard a sailboat and we can say with absolute sincerity that every single minute lived on that boat was special. Sea, landscapes, sunsets, relaxation and lots of fun: everything was just perfect. A special thanks goes to Mirko, our skipper, a truly fantastic person: very prepared, professional, attentive and always available. He was able to make the journey even more enjoyable, conveying safety and, at the same time, creating an atmosphere of great conviviality and fun. You can immediately perceive his experience, his passion for the sea and the great seriousness with which he carries out his work. With him we always felt in excellent hands and we were able to fully enjoy every moment, without worries. We absolutely recommend this experience, without any hesitation, to anyone who wants to experience the sea in an authentic and special way. Seriousness, professionalism, competence, fun and a beautiful atmosphere: we really couldn't ask for anything better. Thank you Mirko for making this trip to the Pontine Islands an unforgettable experience. We will definitely be back!
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South Sardinia - A Marine Paradise to Explore!

09/11/2026

Mariantonietta D.

-

IT

Francesco pampered us throughout the trip with his attention to detail, with his cuisine and above all with his great experience at sea. Thank you Francesco

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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 (35)Pontine Islands (17)Aeolian Islands (16)Liguria (14)Aegadian islands (9)Northern Sardinia (8)Sicily (4)Naples & Amalfi Coast (4)Lake Garda (3)Southern Sardinia (3)

Italy: departures by month

october (59)november (5)december (1)january (1)february (1)march (1)april (3)may (4)june (5)july (6)

Other travel ideas

Sailboat (165)Whole boat with skipper (143)Cooking service onboard (68)Catamaran (52)All inclusive (38)Exotic destinations (21)Courses & regatta (16)Sport & wellness (12)Offshore (9)Day trips (8)

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