109

experiences

4.6

The Saronic jewels with Hydra and Spetses exclusively for four

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

May

€1,250

€1,125

Per person

4.4

The unspoiled paradise of the BVI

Caribbean: BVI - British Virgin Islands

10 days - 10 nights

One departure available

March

€1,350

€1,147

Per person

5.0

Weekend of Sailing and Relaxation

Italy: Liguria

2 days - 1 night

20 departures available

March - August

Starting from

€290

Per person

4.2

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

4.8

Thailand: a dream to discover sailing with a hostess

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

4 departures available

January - December

€1,050

Per person

4.8

New Year's Eve wandering among the islands of Thailand with hostesses

Thailand: Phuket, Krabi and Phi Phi Islands

11 days - 11 nights

One departure available

December - January

€1,646

Per person

5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

20 departures available

June - October

Starting from

€1,100

Per person

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

21 departures available

May - October

Starting from

€590

Per person

4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

11 departures available

June - September

Starting from

€736

Per person

5.0

Raja Ampat: a Christmas at the end of the world

Indian Ocean: Indonesia

8 days - 8 nights

One departure available

December

€1,428

Per person

4.4

Guadalupe to St. Martin via Antigua, Barbuda, St. Barth, and Anguilla

Caribbean: Saint Martin

14 days - 14 nights

One departure available

February

€1,490

€1,341

Per person

4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

31 departures available

April - November

Starting from

€650

€618

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

19290 reviews

Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

11/3/2026

Paolo P.

Excellent experience, boat up to expectations, skipper attentive to the safety of the crew and always available to evaluate every request of the people on board. To repeat the adventure for other destinations.

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

11/3/2026

Alvise V.

Great!

Squid Festival 2026! - Capraia Isola

11/3/2026

Andrea C.

Good experience, too bad for the weather conditions not ideal.

The fantastic Saronic Islands and the surroundings of Athens

10/20/2026

Francesca A.

We spent a beautiful week together with Alessandro.Even if the weather was not the most clement, we were able to visit beautiful and characteristic places that we could never have discovered in any other way. In addition to the fantastic experience itself, it was Alessandro who made the difference: an experienced captain, a true master of life, with a wealth of stories to write a book about. We spent days between the sea, the wind and its stories, eating and drinking together as old friends. Thank you Ale, we will always carry you in our hearts with the hope of meeting again soon. Francesca and Davide

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!