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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!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€410

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August

Starting from

€849

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

5 departures available

September - November

€250

Per person

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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

10 departures available

July - November

Starting from

€500

€425

Per person

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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

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5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August

€650

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

9 departures available

June - October

€650

Per person

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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

2 departures available

July - September

Starting from

€200

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

15 departures available

June - November

Starting from

€600

€540

Per person

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5.0

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

Italy: Aegadian islands

7 days - 7 nights

10 departures available

June - September

Starting from

€700

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

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

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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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

13929 reviews

Midweek relaxing in the Pontine Islands

06/19/2026

roberta r.

-

IT

Beautiful ride. Mirko was great at 360 degrees, the best skipper I have ever had to deal with! Experienced, kind, nice and very proactive. He made us see very beautiful things and stop in beautiful bays. He is also a good cook. Bravo Mirko super skipper!
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Midweek in the Pontine Islands. Between Ponza, Palmarola and Zannone

06/19/2026

Silvia C.

-

IT

Really enjoyable experience. Marco and Giada accompanied us on a beautiful tour of the Pontine Islands making us discover beautiful bays also preparing excellent dishes. Marco is a very attentive and experienced skipper. Comfortable boat, a plus definitely the two sups at our disposal.
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Northern Sardinia and Corsica in a large and comfortable Catamaran

06/19/2026

Lorenzo L.

-

IT

Fantastic holiday from every point of view. The charter unfolds in one of the most evocative locations in the Mediterranean within marine and terrestrial parks. The Lagoon 50 offers comfort on board not comparable to any monohull and nothing is missing among the equipment: tender, SUP, sofas and sundecks, a crazy kitchen and really beautiful cabins.... + comfortable than at home. The transfers were both motor and sailing and in the latter case the experience is truly memorable, 10 knots of effortless speed. The logistics in the port, embarkation and disembarkation were impeccable. The week is perfectly balanced between moments at sea and visits and leisure on land. Maurizio - the skipper and owner - is a host who always makes you feel at ease, very helpful, nice and prepared; I have always had excellent communication. Charter highly recommended! LL

Long weekend of June 2 in the archipelago of La Maddalena and south of Corsica

06/19/2026

Marco R.

-

IT

It was a wonderful experience, from all points of view. The boat is kept in perfect condition and is very comfortable (availability of space, a bathroom for each cabin, for example). The care and attention of skipper Fabrizio in making guests feel at home are of a high level (towel and sheet kit, beautiful and quality, just to give an example). The destinations are beautiful, also thanks to the skipper's advice in finding the most beautiful, less crowded bays. An experience to be recommended and redone. Thank you Fabrizio.! Versione Italiana It was a truly wonderful experience in every respect. The boat, kept in perfect condition, is very comfortable (for example, thanks to the availability of space and a private bathroom for each cabin). The care and attention of the skipper, Fabrizio, in making guests feel at home are of a very high standard (just to give one example, the towel and linen kit provided is beautiful and of excellent quality). The destinations are stunning, also thanks to the skipper's advice in finding the most beautiful and less crowded bays. An experience highly recommended and definitely worth repeating. Thank you, Fabrizio!

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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 (108)Aeolian Islands (60)Northern Sardinia (46)Pontine Islands (45)Aegadian islands (30)Liguria (29)Naples & Amalfi Coast (16)Southern Sardinia (16)Sicily (13)Tremiti Islands (6)

Italy: departures by month

july (241)august (216)september (152)october (41)november (5)december (2)january (1)february (1)march (1)april (1)

Other travel ideas

Sailboat (581)Whole boat with skipper (445)Cooking service onboard (125)Catamaran (92)All inclusive (53)Family sailing cruises (32)Courses & regatta (27)Exotic destinations (26)Day trips (22)Offshore (21)

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