header cover
sailsquare logo

Family sailing cruises yacht sailing holidays & tours in Italy

Discover more than 18 opportunities to get on board a Family sailing cruises adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

cover image
avatar image

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

€441

€419

Per person

cover image
avatar image

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August - September

€750

Per person

cover image
avatar image

4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

4 departures available

September - October

Starting from

€220

Per person

cover image
avatar image

4.8

Super!

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

One departure available

September

€360

€342

Per person

cover image
avatar image

5.0

Super!

Weekend on a sailing boat between Capraia and Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€350

Per person

cover image
avatar image

4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

5 departures available

September - October

Starting from

€363

€290

Per person

cover image
avatar image

4.7

Week between the Tuscan Islands and North Corsica

Italy: Tuscany

7 days - 6 nights

3 departures available

September

Starting from

€600

Per person

cover image
avatar image

4.7

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

Italy: Tuscany

6 days - 6 nights

One departure available

August - September

€1,041

€989

Per person

cover image
avatar image

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

August - September

Starting from

€550

Per person

cover image
avatar image

5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - November

€583

Per person

cover image
avatar image

4.7

Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

Italy: Naples & Amalfi Coast

3 days - 3 nights

2 departures available

September

Starting from

€452

€429

Per person

cover image
avatar image

4.6

Relaxing cruise on the island of Elba

Italy: Tuscany

7 days - 7 nights

One departure available

August

€896

€806

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

298 reviews

avatar placeholder

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

08/20/2025

Rosamaria S.

-

Italy

Our week aboard the [hidden] was an unforgettable experience among the beauties of the Aeolian Islands. Luigi, an experienced skipper and talented engineer, guided us with safety and flexibility, ensuring suggestive stops and safe anchorages at all times. The boat, a vintage-style 13-meter boat with fine wood finishes, is comfortable and well organized: optimized spaces, four versatile cabins and a welcoming dinette allow you to live life on board with the right balance between sportiness and comfort. An added value is represented by Enrico, Luigi's son and architect of naval interiors: in addition to being a skilled navigator, he has proved to be an authentic "director of on-board hotel services", capable of combining logistics, hospitality and cuisine of the highest level. Breakfasts, lunches and aperitifs prepared with the freshest local raw materials – often fish of the day – made every convivial moment special. The familiar and informal atmosphere was the common thread of the cruise, although disembarkations can sometimes be uncomfortable due to the small rowing tender, as the engine supplied is inadequate for shallow waters. The absence of adequate safety accessories (lights, dedicated life jackets) generated significant critical issues in the evening, in a context of autonomous management of the tender by us guests and with not completely calm seas. Despite this not small problem, the rule of always dining on land and independently (necessary to guarantee the team a well-deserved break) has always proved to be a winning choice, allowing you to fully appreciate the picturesque seaside villages and above all the tasty Aeolian cuisine. In summary, despite some small technical limitations, the cruise with Luigi and Enrico remains a unique experience that combines sailing, nature, gastronomy and authentic hospitality. An adventure that we recommend to those who love the sea, the wind and the authentic charm of sailing.
avatar image

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

08/20/2025

Giulia D.

-

Italy

A wonderful holiday. Luca and Tommaso two young but very capable, skilled and super nice skippers! The boat is spacious and allows you to experience the sea in full comfort You eat like God. better than at the restaurant !! Everything was wonderful, thank you guys!!!
avatar placeholder

Weekend on a sailing boat between Capraia and Elba

08/19/2025

Carlotta Giulia S.

-

Italy

A boat from a thousand and one nights, a 10/10 skipper and a lot of good company. Checco, infallible compass of our journey in the blue waters of Elba. Thank you!!!
avatar placeholder

Weekend on a sailing boat between Capraia and Elba

08/19/2025

Michela D.

-

Italy

I had a lot of fun, a group at the top 🤩what can I say.. a wonderful experience with places that look like postcards 🐟 🐠 🏝️ and a tireless 💪🏻 skipper always charged and ready to make us live every moment to the fullest 🐬 🌊 To live and relive absolutely!!

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Italy: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964