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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

15 departures available

June - October

Starting from

€689

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

16 departures available

May - October

Starting from

€540

Per person

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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

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

12 departures available

June - September

Starting from

€600

€540

Per person

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4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

23 departures available

May - November

Starting from

€650

€618

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

7 departures available

May - July

Starting from

€370

Per person

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4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

7 departures available

May - July

Starting from

€650

€585

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

21 departures available

May - October

Starting from

€590

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€680

Per person

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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

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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

12 departures available

May - September

Starting from

€1,000

€890

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

6 departures available

July - September

Starting from

€650

Per person

Why book a holiday with Sailsquare?

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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

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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

17638 reviews

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May Day between Elba and Capraia

05/3/2026

Jennifer G.

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Italy

Enrico is just fabulous. An expert in this particular region. I listened and learned a great deal. It's so comforting to spend time with such a flexible Skipper and a personable gentleman. The bonus was our extended group..... a fun, genuine and loving bunch. I look forward to another sailing experience. Thanks Enrico..

Weekend sailing course from Bandol

05/2/2026

Nathalie R.

-

France

A beautiful sailing discovery stay, in a friendly atmosphere and perfect weather. Thank you
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4 Days Exploring the Chausey Islands from Saint-Malo

04/30/2026

Claire M.

-

France

Four days of pure happiness from Saint-Malo to the Chausey Islands! Skipper at the top: professional, reassuring and hyper attentive to safety. Comfortable, impeccable boat, you immediately feel good. And the icing on the cake: home-made, balanced and delicious meals, prepared by the skipper himself. Total disconnection, a real holiday!

Sailing cruise in the Greek islands - The Saronic Islands

04/29/2026

Marc G.

-

Canada

A week on a roller coaster too windy, no more wind. Mother Nature is in charge! However our skipper was really up to the situation, Alexandre is a good captain and a good GO (nice organizer) his knowledge of the islands and the people who live there adds a lot to the fun and experience. Regarding the boat, although old, it is a very good boat but unfortunately there were several small problems that did not affect our trip, we believe that preventive maintenance could be in order. Thank you again Alexandre for your Carbonaras and the typical Greek evening. Good winds from Quebec Hélène and Marc

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