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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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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

June - September

Starting from

€750

€675

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

2 departures available

August

€1,290

€1,190

Per person

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4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

Starting from

€1,180

€1,080

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

13 departures available

July - October

Starting from

€590

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

11 departures available

July - October

Starting from

€1,300

€1,170

Per person

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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,134

Per person

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4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€390

€351

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

9 departures available

June - September

Starting from

€600

€570

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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4.7

Marmaglia mini-flotilla: discovering the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,140

€1,040

Per person

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4.6

Different flotilla in Ionian Greece: nature, new friends and fun

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,110

€999

Per person

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4.6

Long weekend between Ponza and Palmarola: adventure at the Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

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.

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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

17821 reviews

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Three-Day Sailing Tour to the Pontine Islands

06/21/2026

NICOLA A.

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IT

Excellent experience with a very prepared skipper, no frills, excellent cook and maximum welcome and attention. We have just allowed the weather even sailed a little without an engine. We took the tender several times to better enjoy the islands. He tries to do everything possible to meet the scheduled times and succeeds. Recommended.

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

06/20/2026

Valentina P.

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IT

Our very first sailing experience with Luca, the skipper, was unforgettable. A week of pure relaxation, 24 hours a day at sea, nights at anchor in front of the coves and beautiful cliffs of the Island of Elba, fantastic sunsets sipping our aperitifs, the sunrise with the scent of coffee coming out of the mocha ... moments in which time stops and you finally find the true meaning of life. And what about our skipper Luca... A very kind person, helpful, affable and also discreet, always ready to fulfill any of our requests. I hope it will be the first of a long series! Fair winds to all!! Valentina and Federico
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A week sailing in the most beautiful places in the world

06/20/2026

Daniele M.

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IT

It was a great holiday! We immediately felt like family. Giusy is a magician in the kitchen and Piero was an exceptional master skipper. The games in Burraco and Farkle have reached unattainable levels of competitiveness. It is difficult to describe in a few lines the whole week spent together, but we can say that they are 2 special people.

"Nel Blu dipinto di Blu" - midweek in Ponza, Palmarola and Ventotene

06/20/2026

Fabio F.

-

IT

Everything above expectations, beautiful islands, beautiful boat, exceptional captain. to be repeated absolutely.

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