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Family sailing cruises yacht sailing holidays & tours in Italy

Discover more than 22 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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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

22 departures available

May - November

Starting from

€600

€540

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€400

Per person

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4.9

Super!

On holiday with Dad to discover Elba and Capraia

Italy: Tuscany

4 days - 4 nights

3 departures available

June

€400

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

5 departures available

June - August

Starting from

€800

€720

Per person

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4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

April

€275

Per person

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4.7

2 June: Whale watching expedition with WWF guide on an 18-meter schooner

Italy: Pontine Islands

5 days - 4 nights

One departure available

May - June

€567

Per person

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4.7

Easter: Whale Watching Expedition in Pelagos Sanctuary with WWF Guide

Italy: Liguria

3 days - 3 nights

One departure available

April

€452

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

10 departures available

April - September

Starting from

€310

€279

Per person

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4.8

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

15 departures available

May - September

Starting from

€400

Per person

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4.7

April 25th: cetacean watching expedition in the Pelagos Sanctuary with WWF guide

Italy: Liguria

3 days - 3 nights

One departure available

April

€452

€429

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

5 departures available

August - September

Starting from

€1,041

€989

Per person

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4.7

Whale watching cruise with WWF guide between Northern Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

July - September

Starting from

€999

€949

Per person

Why book a holiday with Sailsquare?

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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

371 reviews

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We have known the Aeolian Islands for 20 years. - Live them with us.

10/20/2025

Marco F.

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Italy

Pasquale is a profound lover and connoisseur of the Aeolian Islands. Beyond the experience at sea, it also suggests excursions and places to visit on land
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Poetic Gulf of Poets

10/9/2025

Massimo G.

-

Italy

Giovanni is a professional at his job,.. Expert, and collaborative with his customers... ADVICE....
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Poetic Gulf of Poets

10/6/2025

Fabiola R.

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Italy

Beautiful experience!! Giovanni is a wonderful person and d a prepared skipper, the itinerary is lovely .... definitely try
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Poetic Gulf of Poets

10/6/2025

Domenico C.

-

Italy

Giovanni is an attentive skipper, very competent and extremely helpful. I recommend it!

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