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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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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

3 departures available

July - August

Starting from

€800

Per person

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4.9

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

2 departures available

August

Starting from

€1,060

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

10 departures available

June - October

Starting from

€800

€720

Per person

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5.0

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

2 departures available

July - September

Starting from

€350

Per person

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5.0

Super!

Weekend between Ponza and Palmarola Comfortable - max 4 people

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€495

€446

Per person

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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

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

9 departures available

June - October

€650

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

6 departures available

July - October

€260

Per person

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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

9 departures available

June - August

Starting from

€250

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

5 departures available

July - August

Starting from

€900

Per person

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4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

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

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

17727 reviews

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4-day cruise course

06/6/2026

Alexis D.

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GB

Superb first experience on a sailboat for my father and I. Fabienne was very pedagogical with us, which allowed us to progress quickly. The boat is very well equipped and sailing around the islands was a very nice experience.

SHARE & SAIL - 5 days Exploring & Relaxing at the heart of Cyclades

06/6/2026

Annina P.

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CH

We had an unforgettable time in the Cyclades! Our skipper Dimitris introduced us to sailing, which was totally new for us but totally exciting and a very nice experience on the sea. It was a great mix of sailing and time on land to explore new places. We enjoyed it very much & highly recommend it:)
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June 2nd long weekend between Procida, Ischia and Ventotene

06/6/2026

Valentina G.

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IT

Really nice long weekend of the second of June, well-kept and comfortable boat and group with which we immediately created harmony, also thanks to Umberto, a nice, prepared skipper and a great connoisseur of the places, who organized everything with care, always making us feel at home
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2 June long weekend - discovering the Gulf of Poets and Portofino

06/5/2026

Annalisa P.

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IT

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

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