111

experiences

4.8

Super!

From Kalamata to Milos: the fantastic and wild South Peloponnese

Greece: Cyclades

7 days - 7 nights

One departure available

July

€850

€765

Per person

4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

€903

Per person

4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

22 departures available

May - October

Starting from

€600

Per person

4.6

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

Italy: Northern Sardinia

6 days - 7 nights

19 departures available

May - October

Starting from

€600

€540

Per person

4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,400

Per person

4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

3 departures available

June

€360

Per person

4.9

Super!

Traveling and Dreaming in the Gulf of Poets - All inclusive

Italy: Liguria

2 days - 2 nights

One departure available

May

€360

Per person

4.9

Super!

"Nel blu dipinto di blu" - Sailing cruise in Northern Corsica

Italy: Tuscany

7 days - 7 nights

10 departures available

June - September

Starting from

€680

Per person

5.0

Super!

Thailand and the Andaman Sea

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

3 departures available

December

€1,450

€1,378

Per person

4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

8 departures available

May - September

Starting from

€220

Per person

5.0

Super!

Dreamy Maldives by sailboat - From Malé to Kulhudhuffushi

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February

€2,650

Per person

5.0

Super!

Seyschelles Islands... Welcome to paradise!

Indian Ocean: Seychelles

11 days - 11 nights

3 departures available

April - June

€2,400

€2,040

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

17617 reviews

A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

Italy

Everything worked out great, Paolo was super helpful!!!! Advice 100%

Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/10/2025

giulia f.

Italy

I participated in the weekend on a sailing boat organized for the Squid Festival and I couldn't ask for anything better! It was a wonderful experience, between sea, wind and excellent company. The crew was great: nice people and with a great desire to have fun. The skipper is super professional, but also helpful and attentive to let us experience sailing in a relaxed and fun way. I can't wait to get back on board for the next adventure! ⚓️🐙✨ Giulia, Eva and Martina

Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/5/2025

Marco F.

Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.

LET'S GO TO TOTANI - Festival in Capria

11/5/2025

Marco D.

Italy

Unforgettable and fun experience, very prepared skipper who tamed a sea that was not exactly docile. The fishing competition is beautiful and suggestive.

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 2035144220

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!