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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!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

6 departures available

September - October

Starting from

€370

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

€466

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

3 departures available

September - October

€650

Per person

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4.8

Super!

From Tavolara to Ogliastra, the great emotions of Eastern Sardinia

Italy: Southern Sardinia

5 days - 4 nights

One departure available

September

€1,200

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

One departure available

September

€250

Per person

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4.9

Egadi Islands by catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€1,100

Per person

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5.0

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€350

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

€453

€430

Per person

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5.0

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€295

Per person

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4.8

COUS COUS FEST: Un Week End di Mare, Vela, Cous Cous e Musica!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

7 departures available

September - October

€320

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

30 departures available

January - December

Starting from

€300

€270

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.

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

14874 reviews

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A sailing holiday: discovering the Pontine Islands

08/31/2026

Matilde C.

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IT

Fantastic experience! Fabio is a competent and attentive skipper, both to the weather conditions and to the needs of the group. He guided us between Palmarola, Ponza and Ventotene to discover beautiful bays and caves, also involving us in the maneuvers and handling of the boat and making us live the sailing experience to the fullest! The only flaw is the space: the boat is small and has only one bathroom, so in 6 plus the skipper it is a bit cramped.
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Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

08/31/2026

Antonio C.

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IT

To be clear: excellent experience, do it. Pros: - convenient departure, parking in Punta Ala, boarding and disembarking luggage directly in front of the boat; - A great skipper, nice, we sailed whenever we could, that is a lot of hours; - if you are sick of the sea, traveling by sail, only with the sound of the sea and the wind, is an experience; - the roadsteads visited are more than enchanting, so the dozens of baths taken are one better than the other; - the skipper guides the shopping and cooks VERY WELL. Fish couscous, hummus with octopus... So it optimized all the times and at the same time satisfied every palate. In addition, he went out of his way for every need. Cons: - serious voice: you sleep in extremely small spaces, several days it was hot and humid and the ventilation in the stern is entrusted to a small porthole. Fortunately, he has installed a fan in each room, but the noise is remarkable. In short, sleeping is a bit of a problem; - Not very relevant article: there is a lack of communication. Better to clarify, perhaps from Maps, which parking lot can be used. That on Mondays we need a car for shopping, what if we were all on the train? Extremely positive experience, I thank the skipper Riccardo. Don't deny it.
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Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

08/31/2026

Giovanna B.

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IT

Super positive sailing experience! Alberto took us to beautiful places... postcard sea and beaches.... exciting and numerous sails.... fairness and infinite availability in providing us with information and clarifications on the fabulous world of sailing !!! Top cleanliness .... !! Boat very well maintained !! The only flaw...... Time literally flew !!

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

08/31/2026

Luigi M.

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IT

Magnificent experience, perfect Joshua, beautiful places, wonderful travel companions... And I would definitely do it a thousand times over

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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 (37)Aeolian Islands (20)Pontine Islands (18)Liguria (15)Aegadian islands (12)Naples & Amalfi Coast (10)Northern Sardinia (10)Southern Sardinia (5)Sicily (4)Lake Garda (3)

Italy: departures by month

september (126)october (47)november (4)december (1)january (1)february (1)march (1)april (3)may (4)june (4)

Other travel ideas

Sailboat (194)Whole boat with skipper (168)Cooking service onboard (73)Catamaran (55)All inclusive (39)Exotic destinations (23)Courses & regatta (15)Offshore (12)Sport & wellness (9)Day trips (6)

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