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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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4.8

Super!

Introductory sailing course

Italy: Liguria

2 days - 1 night

One departure available

September

€260

Per person

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4.8

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

October - November

€299

Per person

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4.9

Super!

EGADI AND COUSCOUS FEST of San Vito Lo Capo

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€600

Per person

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

One departure available

September

€280

Per person

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4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

October

Starting from

€294

Per person

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5.0

Super!

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

3 departures available

September - October

€99

Per person

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5.0

Super!

Weekend of fun and relaxation on a sailing boat on the island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€250

Per person

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4.9

Super!

Traveling and Dreaming in the Gulf of Poets - All inclusive

Italy: Liguria

2 days - 2 nights

One departure available

May

€360

Per person

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5.0

Super!

Weekend Garda Lake 

Italy: Lake Garda

2 days - 2 nights

One departure available

October

€179

Per person

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4.8

Super!

Weekend sailing in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€290

Per person

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5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

One departure available

October

€69

Per person

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5.0

Super!

Transfer to the Island of Elba

Italy: Tuscany

1 day - 0 nights

One departure available

September

€60

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

13612 reviews

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A week sailing in the most beautiful places in the world

09/15/2025

Federica P.

-

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.

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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.

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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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Magnificent week on catamaran between Corsica and Capraia with Hostess

09/15/2025

Larisa N.

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Italy

Really pleasant holiday in Corsica, with lovely places, and great company and delicious food, however the experience was ruined by the very rude captain who on one occasion left part of the passengers on an island and picked them up after 30 minutes. He was evidently very stressed about the seasonal workload he should have avoided taking this group

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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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