experiences

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

June - September

Starting from

€700

Per person

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

12 departures available

June - October

Starting from

€1,150

Per person

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

June - September

Starting from

€600

€570

Per person

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

Per person

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

8 departures available

June - September

Starting from

€490

€466

Per person

4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

4 departures available

July - August

Starting from

€1,052

Per person

5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

3 departures available

July - August

Starting from

€850

€765

Per person

4.7

Whale watching cruise with WWF guide in the Corfu archipelago

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,052

Per person

4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

17 departures available

June - November

Starting from

€600

€540

Per person

4.7

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

Italy: Liguria

4 days - 4 nights

One departure available

September

€609

€579

Per person

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

€441

Per person

4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

6 departures available

July - September

Starting from

€400

€360

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

415 reviews

June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide

06/10/2026

Guido F.

Beautiful experience. The enthusiasm and ability to involve biologists is remarkable. The only pity we never sailed.

Long weekend of June 2 with WWF guide in the heart of the Tuscan Archipelago

06/10/2026

Enrica Caterina B.

Great company! Interesting information about cetaceans and very prepared and patient WWF guide. We spotted dolphins and manta rays. Very nice skipper. A somewhat old boat. We didn't find much wind, so we couldn't do much sailing, because otherwise we wouldn't get to the sighting areas in time

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

06/8/2026

Ewout (Eduardo) G.

Excellent week of sailing & chilling in beautiful bays & ports!

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

06/8/2026

Giovanna G.

A fantastic experience for anyone who loves the sea and wants to discover more about its marine life.

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!