header cover
sailsquare logo

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

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

cover image
avatar image

4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

August - October

Starting from

€200

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

4 departures available

August - September

Starting from

€650

Per person

cover image
avatar image

5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€935

€748

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

3 departures available

August - September

Starting from

€1,041

€989

Per person

cover image
avatar image

5.0

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - November

Starting from

€650

€585

Per person

cover image
avatar image

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

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

7 departures available

July - September

Starting from

€550

Per person

cover image
avatar image

4.7

Ibiza All Inclusive on an 18m ketch with skipper and skipper

Spain: The Balearic Islands

6 days - 7 nights

3 departures available

July - August

Starting from

€1,200

Per person

cover image
avatar image

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

cover image
avatar image

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

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

3 departures available

September

Starting from

€420

€399

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 - Sailing and Catamaran Holidays for Families

210 reviews

avatar placeholder

Whale watching mini-cruise with WWF guide between Liguria and the French Riviera

07/15/2025

Tecla V.

-

Italy

Very nice and competent WWF skipper and popularizer. Pleasant trip. travel companions too I don't give 5 stars for the simple fact that on the poster presenting the trip it was written return at 4 pm on Sunday, while in reality the trip ended in the morning at 9., and having known it I would have organized myself better with the means of transport.
avatar placeholder

Whale watching mini-cruise with WWF guide between Liguria and the French Riviera

07/14/2025

Valentina D.

-

Italy

A super empathetic, prepared and helpful WWF guide, a person who loves his job and transmits enthusiasm to others as well; we learned a lot of interesting things, Skipper also super recommended for sympathy, availability and professionalism in dealing with any unforeseen events. Small note not addressed to the guide who had to comply with the directives, Unfortunately the last of the 3 days we had to go, for research needs, to an area with little probability of sighting, where in fact we did not see anything; Personally, since it was a holiday of only 3 days, I would have avoided losing one. Anyway super recommended.
avatar image

Week between the Tuscan Islands and North Corsica

07/14/2025

Flavia G.

-

Italy

Francesco is an experienced skipper, skilled in managing the unexpected and meeting the needs of the whole crew. The boat is comfortable and equipped with everything you need to spend a pleasant holiday.
avatar image

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

07/14/2025

Francesca N.

-

Italy

Excellent experience, the [hidden] is a spacious and very well maintained boat, updated with many small features that make it very comfortable. Captain Luca immediately showed that he knows his boat and the area in which he sails like the back of his hand and has earned everyone's trust from the beginning, even when the weather was not favorable, always making us part of his decisions. Tommaso, despite being very young, was a constant support, always very kind and attentive to everyone's needs, but also very nice and always ready for a joke. Above all, he is an excellent cook and together with Luca he spoiled us all week with excellent aperitifs, lunches and dinners. As for the area, I think it needs no introduction, the sea is crazy and the islands one more beautiful than the other. Ultimately a holiday to be repeated!

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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