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

2 departures available

October

€1,300

Per person

4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October - November

€585

Per person

4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October

€750

Per person

4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

Starting from

€453

Per person

5.0

Super!

Barcolana Weekend: experience the largest regatta in the world

Italy: Venice and the Gulf of Trieste

3 days - 2 nights

One departure available

October

€420

Per person

5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

€570

Per person

5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

2 departures available

October

€370

Per person

5.0

Super!

Daily sailing trips to Ortigia and Plemmirio

Italy: Sicily

1 day - 0 nights

30 departures available

October - November

€150

Per person

5.0

Super!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

5 departures available

October - November

€300

Per person

4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

3 departures available

October

€230

Per person

4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

4 departures available

October - November

€350

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 - Sailboat holidays & skippered tours

19252 reviews

We have known the Aeolian Islands for 20 years, live them with us!

10/4/2026

Livia R.

Everything perfect.. Very well organized. Very nice and engaging experience.

Corfu between bays, taverns and myths.

10/4/2026

Clara M.

A very pleasant and peaceful experience. Despite being the last outing and carrying the exhaustion of the season, they did everything possible to make us comfortable and the alternatives they gave us when there was bad weather were very good ideas. The treatment is very nice, the kitchen too. The beautiful sailboat, very cozy, you feel at home. The only thing is that we thought we were going to make more stops and sailing trips and discover more hidden places and we were left wanting more, but it was mainly because of two days of bad weather. We will repeat the experience for sure

Aeolian Islands: between sea and authentic flavours

10/4/2026

Lorenzo F.

Fantastic experience discovering the Aeolian Islands. The holiday followed very natural rhythms in the name of relaxation. Our skipper Carlo was super! Always available and easy-going, with his great passion and professionalism he guided us to discover wonderful coves and islands. The group got along right away. Between the sea, laughter, aperitifs and crazy sunsets, it is a holiday that I would do again without thinking about it. Recommended!

Sailing, swimming and aperitif at sunset ... What else?

10/3/2026

Victoire D.

Perfect afternoon with Emanuele! Wonderful host, generous food and drink and the boat is beautiful and welcoming Many thanks!!

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!