experiences

4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

3 departures available

October

€320

Per person

5.0

Raja Ampat: New Year's Eve in the last paradise

Indian Ocean: Indonesia

12 days - 12 nights

One departure available

December - January

€2,070

Per person

4.8

Offshore and night navigation course on cabin cruisers

Italy: Tuscany

3 days - 2 nights

One departure available

October

€332

€299

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

5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

4 departures available

October - November

€723

Per person

4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

October - November

€700

€665

Per person

4.7

Tenerife and La Gomera aboard an 18 m ketch

Atlantic islands: Canary Islands

6 days - 7 nights

10 departures available

January - December

Starting from

€900

Per person

5.0

New

Basic and advanced sailing courses

Italy: Liguria

2 days - 1 night

3 departures available

October - November

Starting from

€220

€198

Per person

New

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

May

€450

Per person

4.7

From Funchal to Lanzarote: adventure and unforgettable emotions

Atlantic islands: Canary Islands

6 days - 7 nights

One departure available

December

Starting from

€900

Per person

4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

2 departures available

October

€690

Per person

4.7

Tuscany and Liguria, we sail between the Apuan Alps and the Gulf of Poets

Italy: Liguria

2 days - 2 nights

One departure available

April - May

€300

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

19253 reviews

Egadi paradise for sailing and snorkeling

10/4/2026

Luzia K.

Unfortunately, a wonderful week has come to an end. Mario is a great skipper and host. I can't even list all the bays where we swam in the crystal clear water. Gaia took very good care of us. Nice people, sun, absolutely relaxed.

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!

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!