header cover
logo

Log in

Sailing and Catamaran Holidays for Families

Exploring the turquoise waters of the Mediterranean's most beautiful archipelagos by sailboat is a magical experience for the whole family. Each day becomes an unforgettable chapter of a sea adventure immersed in nature: children have fun exploring pristine bays, swimming with fish, learning to sail, while parents relax in complete serenity.

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

€920

Per person

cover image
avatar image

4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

9 departures available

August - October

Starting from

€1,300

€1,040

Per person

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

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

Per person

cover image
avatar image

4.8

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€750

€675

Per person

cover image
avatar image

4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

Starting from

€700

Per person

cover image
avatar image

4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

September

€400

Per person

cover image
avatar image

4.8

Super!

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

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

€466

Per person

cover image
avatar image

4.7

Mini-cruise with WWF guide in the heart of the Tuscan Archipelago

Italy: Tuscany

4 days - 4 nights

One departure available

September

€567

Per person

cover image
avatar image

4.9

Weekend di relax alle isole Eolie: Lipari, Vulcano e Salina

Italy: Aeolian Islands

3 days - 2 nights

7 departures available

September - October

€320

Per person

cover image
avatar image

4.6

Enjoy: in the blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 6 nights

One departure available

August - September

€750

Per person

cover image
avatar image

4.7

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

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September

€999

€949

Per person

Why book a holiday with Sailsquare?

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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 - Sailing and Catamaran Holidays for Families

496 reviews

avatar image

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

08/9/2026

Martina M.

-

IT

It was a wonderful experience. A very professional crew but above all a very nice family, the guide was the greatest cetacean expert so a fantastic experience.
avatar image

Aeolian Islands: between sea and authentic flavours

08/8/2026

Irene S.

-

IT

Carlo was a fantastic skipper: attentive, professional and passionate. He guided us between the islands with confidence and passion, making us experience for the first time the beautiful feeling of turning off the engine and sailing! Always ready to answer our thousand questions about boating with infinite patience, and then how can we not mention that delicious calamarata, prepared with fish caught right among the boats? One of the best memories of this experience. Life on a boat is all about shared spaces, collaboration and small compromises, but waking up to the sound of the waves and falling asleep under a sky full of stars is worth it all. It is an experience that we recommend to everyone. Unfortunately, due to the weather and strong winds, we were unable to see two of the planned islands. It will definitely be a good excuse to come back!
avatar image

Sailing cruise to the Pontine: wonders a stone's throw from Rome

08/7/2026

Manuel C.

-

IT

The Pontine on an Old Style sailboat are pure magic. The skipper was impeccable: professional, attentive and able to make us experience the sea to the fullest, including delicious dishes, postcard anchorages and tender rides in the most evocative caves of Palmarola, the weather conditions did not allow sailing, but the skipper managed the navigation with professionalism, making every move safe and pleasant. Too bad that the travel company described this fantastic week with unfounded claims and criticisms. But the experience, thanks to the skipper and the places, remains truly special.

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

08/5/2026

Andrea B.

-

IT

Beautiful experience. Initial fears of seasickness or the absence of a proper shower turned out to be excessive. Giovanni is a really competent and caring skipper, plus his passion for cooking also makes him an excellent chef! The Aeolian Islands are one more than the other and the coves where we stopped were amazing! The boat is super comfortable and the spaces more or less adequate to expectations.

Customer Support

customer support

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!

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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