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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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4.7

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

2 departures 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

6 departures available

July - August

Starting from

€870

Per person

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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

€1,134

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

5 departures available

July - September

Starting from

€600

€570

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

€950

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

€1,200

€1,080

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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4.7

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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4.6

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,110

€999

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

5 departures available

July - September

Starting from

€900

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

18027 reviews

Midweek sailing trip in the Gulf of Naples

07/12/2026

Ahmed Y.

-

ES

A fantastic experience, good company and a captain of captains! I would definitely repeat
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Midweek relaxing in the Pontine Islands

07/12/2026

Riccardo G.

-

IT

Mirko is an excellent skipper with a lot of experience, very nice and helpful. The tour was beautiful. The only note to be made was the management of the galley: the skipper did not give clear instructions either for the initial expense or for the responsibility of preparing lunches and dinners, we did not know each other, the result was somewhat anarchic and improvised meals; In the end we did very well anyway.
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/12/2026

valentina t.

-

IT

First (but I hope it won't be the last!) boat holiday experience. It lasted a week, but time seemed to dilate and flow slowly, in pleasant company. Seeing the islands from the sea offers another dimension, breathtaking places, views and colors. Too bad that the variety of species on the seabed appears "impoverished". We sailed little, almost always by motor, but certainly more easily.
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Mini whale watching cruise with WWF guide between Ponza and Palmarola

07/11/2026

beatrice c.

-

IT

The trip exceeded my expectations thanks to Luca and Andrea. Andrea, our naturalist guide was always available at any time for any curiosity of the group, competent in the subject, generous, with remarkable soft skills, a serious young man, intelligent educated a reliable professional with great psychological balance. Luca, our skipper was a firm point, skilled, safe always attentive to our personal safety and to the boat, wise, polite, direct and directive the right: truly a great leader! Luca and Andrea are a couple that works very well, they know how to work in a synergistic, harmonious way, this makes them highly reliable, moreover excellent listeners and also funny!! With them I would go anywhere, relying on myself completely. I found the boat a bit too old and uncomfortable for 10 people, in my opinion Luca and Andrea and another person had to adapt a lot, even if I never heard a complaint from them. I thank you for all the welcome I received and for the joy I experienced.

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