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Yacht sailing holidays & skippered tours in Italy

Discover more than 215 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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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,190

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€900

Per person

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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€719

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August - September

Starting from

€650

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

August

Starting from

€200

Per person

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4.7

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August - September

Starting from

€650

Per person

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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

One departure available

August

Starting from

€583

€525

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

August - September

Starting from

€751

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

2 departures available

August - September

Starting from

€1,041

€989

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August - September

Starting from

€615

Per person

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4.8

Super!

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€820

Per person

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4.8

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€530

€504

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

12607 reviews

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Four days of sea, nature and fun in the Pontine Islands!

07/19/2025

CLAUDIO G.

-

Italy

On the non-holiday I can only make two observations: the extreme professionalism and elegance of the Skipper Fabrizio and the exact opposite of Sailsquare in the relationship with customers who have only had inconveniences
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Tour of Elba and Capraia on a Catamaran

07/19/2025

Rosario C.

-

Italy

Absolutely above expectations, Fabio's catamaran is equipped with every comfort and the skipper pampered us throughout the trip: he knows the beaches, the best restaurants and the places for the best aperitifs and what is not obvious and available to disembark you with the tender on every occasion. He also prepares excellent meals on board as well as being a person of great generosity. In short, highly recommended
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Pontine Islands aboard a splendid 16-meter sailboat

07/19/2025

Paola G.

-

Italy

Four unforgettable days in the Pontine Islands, a simply fantastic holiday! An experience for me definitely to be repeated, and, above all, to recommend to those who love the sea to live at least once in their life to savor a type of journey made mainly of sharing with others and connection with nature! A round of applause to Leonardo, our skipper/captain, and to his wife Elena, second in command, the icing on the cake, who with great competence, professionalism and availability made us explore a small corner of paradise at sea! Together, with the rest of the hilarious crew, to whom my thanks also go to them, we shared everything, endless laughter, dinners on board and on land, in short, indelible memories! See you soon, fair winds, Paola 🥰🤩😍
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Aeolian Islands: blue seen from a sailboat

07/19/2025

nicole b.

-

Italy

A group of 10+2 crew is too much for a boat of that size, which involved logistical difficulties for lunches/dinners, showers and shared bathrooms. Itineraries not always shared, but to the preferences of a group. Moorings in the distant roadstead to make the islands by night (except Salina and Lipari). Questionable navigation plan, as the islands could have been built in reverse due to the weather / wind conditions.

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