experiences

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

3 departures available

October

€1,300

Per person

4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€750

€675

Per person

4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

4 departures available

October

€320

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

564 reviews

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

09/21/2026

Gioia S.

Amazing experience ! I recommend this alternative method of holidays to everyone to have a little more awareness of the world in which we live and to continue to discover the sea.... I will definitely do it again!

Aeolian Islands: between sea and authentic flavours

09/20/2026

Manuela M.

Beautiful experience!! The skipper immediately put us at ease! Too bad it's over!!!!

Whale watching mini-cruise in the Pelagos Sanctuary with WWF guide

09/17/2026

Cecilia A.

Beautiful, I absolutely recommend! Flavia and Gianni were top! Beautiful experience and we spotted Bottlenose Dolphins :)

Week between the Tuscan Islands and Northern Corsica

09/16/2026

Rosanna B.

Fantastic experience!! Splendid and very comfortable boat, wonderful itinerary!! Francesco is a very prepared, kind skipper, always present and attentive to any problem that may arise. He also knows the places on the itinerary very well and also provides very useful information on how to get around on land... I can only thank him!!

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!

Call us at

+44 20 3514 4220

Read our

Contact & Support

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!