612

experiences

4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€650

€585

Per person

4.4

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

13 departures available

June - September

Starting from

€730

€657

Per person

5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

2 departures available

July - September

Starting from

€750

Per person

5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - August

Starting from

€850

€765

Per person

4.7

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

€999

Per person

4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

5 departures available

June - September

Starting from

€312

Per person

5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

6 departures available

June - August

Starting from

€900

Per person

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

8 departures available

June - September

Starting from

€650

€585

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

4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

17 departures available

July - November

Starting from

€540

€513

Per person

4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

July

Starting from

€390

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

17741 reviews

Weekend of the Pontine Islands to discover Ponza and Palmarola

06/8/2026

Ilaria A.

Unforgettable experience! Marco and Giada are fantastic, attentive to everyone's needs, flexible and ready for any experience. The boat is home to it's nice to share every space. I wish you a journey like this, a journey of the soul between the waves of the sea and the waves of the wind.

Weekend of approach to sailing in the setting of the Gulf of Poets

06/8/2026

Chiara B.

Fantastic weekend and experience absolutely to be repeated. Thanks to Commander Sandro! See you next time!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

06/8/2026

Laura S.

Everything perfect - a particularly beautiful week

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!

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!