383

experiences

4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

12 departures available

August - November

Starting from

€700

€665

Per person

4.8

Super!

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

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August - September

Starting from

€600

€540

Per person

4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

Per person

4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August - September

Starting from

€850

Per person

5.0

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

6 departures available

August - September

Starting from

€790

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

5 departures available

September - November

€585

€527

Per person

5.0

Super!

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

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September

€950

Per person

4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€750

€675

Per person

5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€600

Per person

4.8

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

September

€400

Per person

4.7

Super!

Cruise for Singles from Sanremo to Saint-Tropez

France: French Riviera and Porquerolles

8 days - 7 nights

One departure available

August

€750

Per person

5.0

Super!

Sailing & Trekking to discover the Island of Elba

Italy: Tuscany

4 days - 3 nights

One departure available

September

€530

€477

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

18250 reviews

Wind & Wine: the Croatia you don't expect on the Kvarner islands

07/30/2026

Bruna C.

The holiday met our expectations: We sailed, shared moments of conviviality with new people.

Discover the Egadi Paradise by sailboat from San Vito Lo Capo

07/29/2026

Marta P.

The skippers were very good, professional, fun and company. Egadi is a paradise on earth, an ideal destination to make peace with the world. Super comfortable and spotless boat... If the wind decides to participate, it sails which is a fairy tale. thanks Jo! thanks Andre!

Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/29/2026

Maria Z.

Very nice experience, skipper super helpful to make us appreciate wonderful bays and beaches of the Pontine islands,

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

07/29/2026

Claudio A.

A sailing holiday simply fantastic! An unforgettable experience, between sea, relaxation and adventure. The skippers were very good: professional, prepared, helpful and always attentive to everyone's needs. (Very comfortable boat). They gave us beautiful moments, showing great attention to us, creating a very special atmosphere on board. Highly recommended, I can't wait to leave!

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!