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Yacht sailing holidays & skippered tours in Italy

Discover more than 45 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

October

Starting from

€200

Per person

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4.9

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October - November

Starting from

€530

€477

Per person

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4.8

Super!

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

2 departures available

October

Starting from

€850

€808

Per person

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4.9

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€751

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

Starting from

€260

€247

Per person

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4.8

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

Italy: Aeolian Islands

5 days - 4 nights

2 departures available

October

€590

Per person

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4.7

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

October - November

Starting from

€1,455

€1,382

Per person

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5.0

Super!

Experience in the Egadi Islands: A Dream on a Sailing Boat

Italy: Aegadian islands

7 days - 7 nights

3 departures available

October

Starting from

€400

€360

Per person

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4.2

Stuffed anchovies: magical weekend from Genoa

Italy: Liguria

2 days - 2 nights

2 departures available

October

Starting from

€265

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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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

October

Starting from

€615

Per person

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5.0

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

4 departures available

October

Starting from

€337

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

12502 reviews

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

07/7/2025

Claudia D.

-

Italy

Tutto super!
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Traveling and dreaming in the Gulf of Poets - All Inclusive

07/7/2025

Michele T.

-

Italy

Weekend fantastico, all’insegna del relax, mare, ottima compagnia e divertimento. Francesca e Giorgio sono stati accoglienti, professionale e ci hanno coccolati preparandoci prelibatezze e aperitivi super. Da rifare sicuramente!!
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On board with the chef at the Egadi Islands

07/7/2025

Gianmarco G.

-

Italy

Una prima esperienza di vacanza in barca a vela bellissima e rilassante! Il giro alle Egadi è stupendo, abbiamo avuto un assaggio anche della parte più autentica di queste isole, grazie a Max che è uno skipper esperto e uno chef eccezionale, ci ha coccolato con i suoi piatti per tutta la vacanza e ha saputo organizzare il giro ideale non solo rispetto alle nostre aspettative, ma anche in base alle condizioni del vento e del mare. Abbiamo passato 7 giorni tra bagni meravigliosi, deliziosi manicaretti, tante chiacchiere e risate. Esperienza assolutamente consigliata, che sicuramente ripeteremo!
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Long weekend among the wonders of Elba and Capraia

07/7/2025

Marco M.

-

Italy

… Marco skipper… professionale,… ospitale …. simpatico. La barca … una signora… che… porta bene i suoi anni 😊

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