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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.

490

experiences

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5.0

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

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+86 travellers

have booked

Starting from

€99

Per person

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4.8

Little sailors grow up: 5 days sailing on the island of Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

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+5 travellers

have booked

€490

Per person

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The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

Starting from

€700

Per person

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4.8

All in the Family: 5 days sailing on Elba on a comfortable 17m boat

Duration:

4 days - 4 nights

Italy:

Tuscany

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+12 travellers

have booked

€490

Per person

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4.4

Sailing Excursion Alghero ( Skipper + Hostess )

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€90

Per person

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5.0

A fantastic day on a boat in the blue sea of Tuscany

Duration:

1 day - 0 nights

Italy:

Tuscany

Give this experience a try!

€130

Per person

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5.0

3 DAYS 2 NIGHTS Sailing the Ligurian Coast from GENOVA

Duration:

3 days - 2 nights

Italy:

Liguria

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+7 travellers

have booked

Starting from

€324

€360

Per person

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5.0

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

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+10 travellers

have booked

Starting from

€69

Per person

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5.0

First dives in the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

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+17 travellers

have booked

Starting from

€400

Per person

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4.6

Ponza and its wonders

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€400

Per person

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4.9

Long weekend sailing between Elba and Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

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+29 travellers

have booked

€320

Per person

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5.0

Weekend sailing among the Pontine Islands

Duration:

3 days - 3 nights

Italy:

Pontine Islands

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+3 travellers

have booked

Starting from

€360

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

10929 reviews

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Let's discover the Aeolian Islands together by sailing

05/18/2024

Eros Giorgio M.

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Italy

Bellissime le Eolie, bella la combinazione vela ed escursioni, piacevole il gruppo e Mario un esperto ed affidabile velista.
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Weekend at the Pontine Islands: Ponza and Palmarola

05/18/2024

Giulio S.

-

Italy

Una tre giorni davvero bella. Tempo splendido, Ponza ancora con pochi turisti. Marco, oltre che uno skipper esperto, è una persona incredibile, generosa, amichevole e a Ponza conosce tanti luoghi e persone. Ci ha fatto passare momenti di relax, tra buon cibo, buona musica, belle foto scattate e tanti aneddoti. Pur essendo una persona che non fa amicizia velocemente mi sono trovato subito bene con lui e gli altri viaggiatori. Mi piacerebbe vedere le Eolie con lui. Lo consiglio!
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In the blue of Capri and the infinity of the Amalfi Coast

05/15/2024

simona b.

Esperienza stupenda! Grazie per la disponibilità e la simpatia ! A presto!
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An unforgettable sail to discover the Egadi Islands

05/14/2024

Marco B.

-

Switzerland

Bel giro, bella compagnia e ottimo equipaggio

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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

Other travel ideas

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