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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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4.9

Weekend of relaxation and fun from Genoa

Italy: Liguria

2 days - 2 nights

3 departures available

October

€300

€285

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

One departure available

October

€275

€248

Per person

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3.0

7 islands in comfort and convenience

Italy: Aeolian Islands

6 days - 6 nights

7 departures available

September - November

Starting from

€600

Per person

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4.6

Weekend at the Marine Protected Area of the Tremiti Islands

Italy: Tremiti Islands

2 days - 2 nights

One departure available

September

€159

Per person

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4.3

Magnificent weekend of sailing on the island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€225

Per person

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4.2

Stuffed anchovies: magical weekend from Genoa

Italy: Liguria

2 days - 2 nights

2 departures available

October

€265

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

September - October

Starting from

€625

Per person

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4.9

Catamaran cruise to discover Amalfi, Capri, Positano, Ischia

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

October

€1,480

€1,332

Per person

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4.8

Trekking & Sailing Experience-Weekend lungo a Capraia, 2 barche

Italy: Tuscany

4 days - 3 nights

One departure available

September

€450

Per person

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4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

One departure available

September - October

€240

Per person

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4.9

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

3 departures available

September - October

€590

Per person

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4.9

Four days exclusively on Elba between aperitifs and sailing

Italy: Tuscany

4 days - 3 nights

One departure available

September

€283

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

13613 reviews

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A week in the Aeolian Islands - 6 islands in seven days

09/15/2025

Ilaria I.

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Italy

Top experience! Nicola, the skipper, is nice and super reliable, he took us to magnificent places, he was understanding to put up with us all, always available even with the kitchen, but never intrusive, and proposed an itinerary based on the weather that allowed us to see 6 islands, and allowing those who wanted to disembark on land and take turns in the village, or stay on the boat for those who, like me, prefer to enjoy the beauty of the roadstead. Very beautiful and spacious boat, as much as a sailboat can be, equipped with many small modernity and comforts. Even the group that was created with the other participants was beautiful and cohesive, leaving everyone their own freedoms. The journey to reach the Aeolian Islands and to return, starting from Livorno, was not the easiest and most direct, but it was really worth it, so don't be discouraged but leave and choose Nicola, a man of the sea and experience, and you will feel "safe". What to add if not one I hope "see you soon!" Thank you Nicola and your [hidden]!
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A week sailing in the most beautiful places in the world

09/15/2025

Federica P.

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Italy

Nice experience with Giusy and Piero, exceptional skippers and exquisite cooks. Following the wind and currents of the period, Giusy and Piero managed to make us feel at home in their boat and make us enjoy the landscapes and the spectacular sea of Sardinia and Corsica. Two exquisite people with whom we spent a delicious week that I think we will repeat soon.
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Magnificent week on catamaran between Corsica and Capraia with Hostess

09/15/2025

Gaia T.

-

Italy

I give two stars respectively to hostess Manuela and travel companions. For the rest, the nervousness and unjustified anxiety of the commander led to a very unpleasant situation. A lot.
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Sardinia and Corsica on comfortable 15-metre boat with private bathroom in cabin

09/15/2025

Nadezda O.

-

Switzerland

Andrea and Calogero made our boat trip incredible and unforgettable. We met very kind Italians during this journey and, in the end, we became like a family. We celebrated my daughter's 18th birthday all together, and she was very happy to celebrate it with such a wonderful team! Each member of our team stayed until midnight so that we could open the bottle of champagne and celebrate my daughter's birthday. I really appreciate all the attention, friendship, and positive emotions we shared together. We visited many beautiful places and also tried Sardinian and Corsican restaurants. Andrea showed us and introduced us to a wild pink island, which was just a wonderland! We swam a lot :), which was marvelous. It was an extraordinary experience to see the boat flying :) with the wind and its sail open! Andrea and Calogero are great skippers! We also appreciate Sara's care and hope that we can meet her next time. Thank you for this trip! Andrea and Calogero made our boat trip incredible and unforgettable. We met very kind Italians during this trip and, in the end, we became like family. We celebrated my daughter's eighteenth birthday together, and she was very happy to celebrate it with such a wonderful team! Each member of our team stayed until midnight so we could open the bottle of champagne and celebrate my daughter's birthday. I really appreciate all the attention, friendship and positive emotions we shared together. We visited many beautiful places and also tried Sardinian restaurants and Corsicans. Andrea showed us around and introduced us to a wild pink island, which was simply a wonderland! We swam very :) which was fabulous. It was an amazing experience to see the boat fly :) with the wind and the sails open! Andrea and Calogero are great skippers! We also appreciate Sara's care and hope to meet her next time. Thank you for this trip!

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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 (25)Aeolian Islands (16)Liguria (14)Naples & Amalfi Coast (10)Aegadian islands (9)Pontine Islands (9)Southern Sardinia (5)Lake Garda (5)Sicily (4)Tremiti Islands (3)

Italy: departures by month

october (56)november (11)december (4)march (1)april (2)may (5)june (2)july (2)august (2)september (2)

Other travel ideas

Sailboat (167)Whole boat with skipper (127)Cooking service onboard (45)All inclusive (40)Catamaran (38)Exotic destinations (36)Courses & regatta (14)Sport & wellness (13)Day trips (12)Family sailing cruises (10)

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