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Family sailing cruises yacht sailing holidays & tours in Italy

Discover more than 26 opportunities to get on board a Family sailing cruises adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

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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

5 departures available

July - September

Starting from

€650

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

August - October

Starting from

€200

Per person

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5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€935

€748

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

4 departures available

July - September

Starting from

€1,041

€989

Per person

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5.0

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - November

Starting from

€650

€585

Per person

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4.7

Dolphins & Whales cruise with WWF guide – Ligurian Sea

Italy: Liguria

5 days - 6 nights

4 departures available

July - September

Starting from

€830

€789

Per person

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4.7

Whale watching cruise with WWF guide between Tuscany and Northern Corse

Italy: Tuscany

6 days - 7 nights

7 departures available

July - September

Starting from

€1,041

€989

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€550

€523

Per person

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4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

4 departures available

September - October

Starting from

€294

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€420

€399

Per person

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4.7

Whale watching cruise with researcher between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

2 departures available

July - August

Starting from

€925

€879

Per person

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4.6

Week between the Tuscan Islands and North Corsica

Italy: Tuscany

7 days - 6 nights

6 departures available

July - September

Starting from

€600

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 - Family sailing cruises yacht sailing holidays & tours in Italy

182 reviews

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Capri LightBlue and Positano BluSKy

07/8/2025

Kaled E.

-

Italy

Mi familia y yo hemos vivido una experiencia de ensueño en un velero fantástico. Capri, Positano, Bagni della Regina, Li Galli, sitios estupendos, aguas de un azul indescriptible. Gennaro como skiper demuestra una competencia más allá de cualquier duda, metódico, lógico, didáctico (siempre ofrece una explicación del porqué y de como hacerlo), siempre gentil, sereno y atento de cualquiera de nuestras dudas o de lo que necesitáramos. Una navegación impecable y segura. Nuestros compañeros de viaje, como si nos conocieramos de una vida. Altamente recomendada, por supuesto que repetiremos.
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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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Capri LightBlue and Positano BluSKy

07/7/2025

Francesco L.

-

Italy

Esperienza meravigliosa, skipper impeccabile nella sua disponibilità, compagnia super. Assolutamente da ripetere
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Aeolian Islands: between sea and authentic flavours

07/7/2025

Achille V.

-

Italy

Abbiamo vissuto un' esperienza indimenticabile in luoghi incantevoli. Anche grazie alla competenza e simpatia di Emiliano e Nila.

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