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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

12509 reviews

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Weekend on Elba Island

07/8/2025

Giovanna B.

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Italy

Weekend in barca a vela splendido! Tempo ottimo, vele spiegate e piacevoli compagnie . Anthony è skipper molto capace e sempre attivo oltre ad avere un sense of humour vincente!!! Ha cercato sempre di soddisfare ogni richiesta , ha dato indicazioni sui luoghi visti e sulla vita di barca, E' simpaticissimo e .... non ultimo.... un ottimo chef! Ha sempre cucinato piatti gustosi e vari, curandone anche la presentazione !!! E pensare che si i è trovato a bordo vegani , intolleranti al pesce e altro!
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Three-Day Sailing Tour to the Pontine Islands

07/8/2025

Serena R.

-

Italy

Mini vacanza bellissima! Antonio si è dimostrato un grande capitano e un grande uomo. Non solo ha una evidente competenza nautica ma ha anche grandi doti relazionali e ti fa sentire a proprio agio sulla sua confortevole barca. Si è dedicato a tutti noi con passione e gentilezza, portandoci con il suo gommone in tutte le calette e grotte possibili. Ci ha cucinato ottimi piatti e ci ha deliziato con tante storie che riguardavano le isole pontine. La sua barca è estremamente pulita e la cabina di prua una vera reggia! Inoltre la ciliegina sulla torta è il suo mitico tendalino, spazioso e in grado di offrire ampi spazi di ombra! Grazie Antonio, sceglieremmo sicuramente ancora te per una nuova avventura!
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Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess

07/8/2025

sonia s.

-

Italy

-ho trascorso con Paolo e Bianca una vacanza stupenda . Loro sono gentilissimi simpaticissimi Bianca è una cuoca bravissima. Sono molto disponibili . La mia prima esperienza in barca a vela è stata piacevolissima. Ho visto posti stupendi, calette che altrimenti non avrei potuto vedere se non in barca . Consiglio vivamente una vacanza con Paolo e Bianca
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Weekend of sailing and relaxation on Elba

07/8/2025

Andrea P.

-

Italy

Complimenti a Jo …. preparato, disponibile e cordiale. Solo due giorni ma sufficienti per staccare la spina! Consigliato !

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