605

experiences

4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

19 departures available

June - November

Starting from

€420

€399

Per person

4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

5.0

Super!

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

Croatia: Split Archipelago

7 days - 7 nights

11 departures available

June - October

Starting from

€1,200

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

5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August

€650

Per person

4.9

Super!

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

Italy: Tuscany

2 days - 2 nights

3 departures available

June - September

€280

Per person

4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

3 departures available

July

Starting from

€390

Per person

4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

2 departures available

August

€510

€459

Per person

5.0

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

3 departures available

June - July

Starting from

€285

Per person

4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

3 departures available

July - August

€800

Per person

4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - October

Starting from

€600

€540

Per person

5.0

Super!

Four days in Ponza and Palmarola

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

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

17724 reviews

2 June long weekend - discovering the Gulf of Poets and Portofino

06/5/2026

Annalisa P.

Skipper very kind and responsive even pre departure, boat a bit spartan. Destination with very beautiful landscapes, but necessarily a bit "uncomfortable", as there are not many shelters/ports for stops

2 June long weekend on a sailing boat in the beautiful Ligurian setting

06/5/2026

Franco P.

We spent four fun and pleasant days even with wind and sea conditions that were not optimal for sailing

2 June long weekend - Capraia and Cap Corse

06/5/2026

claudio p.

First experience on a sailing boat decidedly positive! Enrico has great experience and is an excellent captain (and cook!), helpful and pleasant company. Thanks to the wonderful weather and the right crew found on board, the long weekend to Corsica was perfect. The boat has all the necessary amenities, with bathrooms in each cabin and spaces suitable for relaxing in the waves. Till the next one!

Long weekend of June 2nd on the Costa Smeralda

06/5/2026

Anna O.

All top :) Francesco serious and reliable, an excellent cook. 4 days of relaxation in Costa Smeralda, to be done again, beautiful experience.

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!