612

experiences

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

4.8

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

One departure available

June

€750

€675

Per person

4.9

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

4 departures available

July - August

Starting from

€410

€369

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

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!

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!

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!

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

4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€800

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

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?

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

17743 reviews

It's time for sun and sea!

06/8/2026

Benedetta D.

Climbing [hidden] is like entering Carlo's house. A hospitable, caring and attentive friend. His boat is beautiful, comfortable but above all maintained with care and with the dedication of a passionate person. Carlo managed to convey his love for the sea and gave us a wonderful weekend of relaxation and approach to the magical world of sailing. I can only recommend this experience and I hope to get back on board as soon as possible!!

Long weekend in Sardinia

06/8/2026

Davide I.

Wonderful group, magnificent places and sea, super skipper!

Weekend of the Pontine Islands to discover Ponza and Palmarola

06/8/2026

Ilaria A.

Unforgettable experience! Marco and Giada are fantastic, attentive to everyone's needs, flexible and ready for any experience. The boat is home to it's nice to share every space. I wish you a journey like this, a journey of the soul between the waves of the sea and the waves of the wind.

Weekend of approach to sailing in the setting of the Gulf of Poets

06/8/2026

Chiara B.

Fantastic weekend and experience absolutely to be repeated. Thanks to Commander Sandro! See you next time!

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