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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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4.5

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,070

Per person

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4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,180

€1,080

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,290

€1,190

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

4 departures available

August

Starting from

€920

Per person

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4.7

Marmaglia mini-flotilla: discovering the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,140

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - September

Starting from

€795

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

10 departures available

August - October

Starting from

€1,400

€1,120

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

10 departures available

August - October

Starting from

€590

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August - September

Starting from

€600

€570

Per person

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4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

4 departures available

August - September

Starting from

€900

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

8 departures available

August - October

Starting from

€570

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

18122 reviews

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Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

07/20/2026

gregoire K.

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FR

A very nice cruise, magical places. Carlo is a beautiful person with a lot of experience and depth. The team we had with us was great. The language barrier (Italian-English) was not a problem, on the contrary it was a richness, and I was able to learn a lot of navigation elements while enjoying a superb walk between porquerolles and blackcurrants. Carlo sets up an atmosphere chaleureuse.et his young and wise side sets the tone for a superb experience.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/20/2026

Andrea C.

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IT

Andrea is very organized and precise. Perfect I would say for a holiday with friends

Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/20/2026

Katia M.

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FR

Thank you to Alessandro and Carlo for a wonderful week. Tutto benissimo. It was also very pleasant to sail not far from his brother Andrea. Very good atmosphere. To be done again.

Whale watching cruise with WWF guide between Northern Sardinia and South Corsica

07/20/2026

Elisa D.

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CH

For me and my son it was a fantastic experience! Thank you!

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