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Yacht sailing holidays & skippered tours in Italy

Discover more than 247 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

247

experiences

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4.2

Easter in Portofino - sailing between the Gulf of Poets and the Tiguillio

Duration:

3 days - 3 nights

Italy:

Liguria

Give this experience a try!

€332

€390

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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56 travellers

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Starting from

€675

€750

Per person

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5.0

Island of Capraia sailing and wild nature

Duration:

4 days - 4 nights

Italy:

Tuscany

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4 travellers

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€405

€450

Per person

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4.9

Super!

Easter sailing between the islands: Elba and Capraia

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€356

€395

Per person

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4.9

Super!

Midweek on Elba, from Monday to Thursday

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€324

€360

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€630

€700

Per person

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4.9

Super!

Long weekend between Elba and Capraia, from Thursday to Sunday

Duration:

3 days - 3 nights

Italy:

Tuscany

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2 travellers

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Starting from

€369

€410

Per person

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Spring in the Cinque Terre

Duration:

2 days - 2 nights

Italy:

Liguria

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4 travellers

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€189

€210

Per person

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5.0

Easter Sailing: Explore the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€495

€550

Per person

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5.0

April 25th and May 1st: sailing to the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€504

€560

Per person

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5.0

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

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5.0

Super!

Easter and Easter Monday with whoever you WANT! to the Pontine Comfortable max 4 pers

Duration:

5 days - 4 nights

Italy:

Pontine Islands

Give this experience a try!

€590

€656

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

12192 reviews

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New Year's Eve 2024 on the Amalfi Coast - All inclusive

01/3/2025

Ilaria C.

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Italy

Straordinario skipper , grande capacità di unire persone interessanti esperienza che intendo rifare proprio con questa barca questo skipper e la qualità delle sue scelte
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New Year's Eve in the Gulf of Naples

01/2/2025

susanna s.

-

Italy

un esperienza bellissima con un comandante e uno skippper meravigliosi . Giorni indimenticabili
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New Year's Eve 2024 on the Amalfi Coast - All inclusive

01/2/2025

Gabriella M.

-

Italy

È stata una piacevole vacanza in ottima compagnia. Lo skipper Fabrizio è una persona competente, simpatica e molto disponibile, oltre ad essere un ottimo cuoco
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The sea and sailing in autumn and winter: 2 days on Elba

01/1/2025

Alessio B.

-

Germany

Ivo, il capitano, è un appassionato velista che ha saputo rendere molto dinamica la veleggiata. L‘ uscita è stata anche molto istruttiva grazie volontà di Ivo di trasmettere la sua conoscenza. Esperienza assolutamente da rifare.

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