613

experiences

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

21 departures available

April - October

Starting from

€460

Per person

5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

17 departures available

May - October

Starting from

€689

Per person

4.6

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

Italy: Northern Sardinia

6 days - 7 nights

16 departures available

May - October

Starting from

€650

€585

Per person

4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

28 departures available

April - November

Starting from

€650

€618

Per person

4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

9 departures available

May - July

Starting from

€650

€585

Per person

4.8

Super!

Ios, Sikinos, Folegandros and Anafi: the fantastic Cyclades of the South

Greece: Cyclades

7 days - 7 nights

2 departures available

August

€990

Per person

5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

5 departures available

July - September

Starting from

€650

Per person

4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

13 departures available

May - September

Starting from

€1,300

€1,170

Per person

4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

22 departures available

May - November

Starting from

€600

€540

Per person

4.6

Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola

Italy: Pontine Islands

3 days - 2 nights

7 departures available

May - June

Starting from

€230

€207

Per person

4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

21 departures available

May - October

Starting from

€600

Per person

5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

9 departures available

May - July

Starting from

€370

Per person

Why book a holiday with Sailsquare?

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Reviews - Sailboat holidays & skippered tours

17620 reviews

Sailing weekend to the Columbretes Islands

04/1/2026

Alicia W.

United States

Had such a fun time!!

Weekend a Capraia, trekking e natura

03/24/2026

Francesco V.

Francesco and Marco are two great professionals, but above all two great travel companions! Highly recommended experience

Weekend a Capraia, trekking e natura

03/23/2026

Niccolò S.

Italy

Francesco and Marco are two very prepared skippers and the perfect people with whom to embark on this type of adventure. Highly recommended.

Four days in the paradise of the San Blas Islands - All inclusive

02/26/2026

Gianluca A.

United States

Luigina and Alessandro made us feel at home since the very first moment. They cooked incredible meals, were always attentive to our needs, and we truly enjoyed spending time with them. It was probably one of our best family sailing adventures. On top of that they made us discover the San Blas islands: crystal clear water, white sand beaches, snorkeling, paddle boarding and of course sailing between the islands. So much to do and a joy doing it with them especially thanks to their deep knowledge of the are. Definitely highly recommended!!

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