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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!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€713

Per person

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4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

2 departures available

August - September

Starting from

€1,010

Per person

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5.0

Super!

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

4 departures available

August - October

€650

Per person

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5.0

Super!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August

€990

Per person

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5.0

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

6 departures available

August - September

Starting from

€790

Per person

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4.9

Super!

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€990

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

4 departures available

August - September

Starting from

€716

Per person

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5.0

New

Corsica Sailing Experience for only 4 people

France: Corsica

7 days - 6 nights

One departure available

August

€900

Per person

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5.0

Super!

One Way from Rio Marina to Porto Vecchio

France: Corsica

3 days - 3 nights

One departure available

August

€290

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

18347 reviews

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La Maddalena Archipelago and South Corsica

08/4/2026

Laura D.

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IT

My friends and I spent a week on a really beautiful sailing boat. Everything was super organized with a beautiful team spirit and a relaxed atmosphere. Between sailing, stops in wonderful coves to swim and discover the marine fauna and flora, everything went well. Definitely to be redone, thanks Gianroberto!

Sailing in Tigullio: Half-Day Experience from Rapallo

08/4/2026

Barbara P.

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IT

Pleasant outing

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

08/4/2026

Lucia S.

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IT

Riccardo combines professionalism with sympathy. He is very patient and helpful and cooks really well.

Gulf of Poets and Cinque Terre

08/4/2026

Veronica B.

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IT

Really nice weekend! Giorgio and Francesca were excellent hosts: nice, helpful and always attentive to the needs of the crew. The boat is spacious, very well maintained and comfortable. We visited beautiful places and spent two days in great company. An experience that we gladly recommend. Thank you Giorgio and Francesca!

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