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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

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

Starting from

€1,180

€980

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

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€795

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!

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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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

August - October

Starting from

€590

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

3 departures available

August - September

Starting from

€900

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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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

One departure available

August - September

€1,041

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

18187 reviews

Let's sail together in Southern Sardinia

07/26/2026

Marina V.

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CH

The boat is small (there were 4 of us + skipper and already very tight, they sell the experience for 6 people + skipper) and the cabin is not very well maintained (in one cabin a piece of wall kept falling), also quite messy (half of the lockers were already occupied with personal belongings or advertising). The destination is quite disappointing, too long distances for a few stopovers we saw 3 bays (saffron, teulada and Pula) and the pretty town of Carloforte in 6 days. The marina of Cagliari where we spent 2 nights is located next to a club with loud music until very late. Showers are paid and outside in front of a parking lot (little privacy). The Marina di Carloforte was better. Very nice and experienced skipper. I would not recommend this for more than 4 people, it is not suitable.

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

07/26/2026

Claudia G.

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IT

My niece and I spent a week full of emotions, new experiences and unforgettable moments. The boat is large, spacious, comfortable, spotless and cared for with great attention by the skippers. The company was fantastic and, during the week, a beautiful friendship was created between all the participants. To make this experience even more special were Luca and Tommaso: two prepared, professional and always available skippers. Thanks to their experience we have sailed in total safety, living emotions that only a sailing holiday can give. In addition to their human and professional qualities, they also deserve praise for the cuisine: every day they prepared fresh, varied dishes, with attention to the smallest details and above all delicious. A real 10 and praise! The places visited are simply stunning, almost paradisiacal, and leave memories that we will carry with us forever. We would leave tomorrow too, but with the same crew! A holiday that we recommend without any doubt.
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Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

07/26/2026

Marina S.

-

IT

Beautiful week, Favorable weather, fabulous travel companions, beautiful places and skipper Sandro kind, competent and always attentive. Thank you for this lovely holiday 👌👌👌
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Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

07/26/2026

Paola M.

-

IT

Beautiful experience. The guide was very knowledgeable and created a great atmosphere on the boat. I have recommended this type of holiday to all friends. I will certainly repeat... Maybe to get to know other corners of the Mediterranean sea... Thank you

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