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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

€700

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - October

Starting from

€590

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

€1,180

€1,080

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

€1,260

€1,134

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

4 departures available

July - September

Starting from

€795

€716

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

10 departures available

June - 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

€1,040

Per person

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4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

2 departures available

June - July

Starting from

€390

€351

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

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4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

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

17779 reviews

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Midweek relaxing in the Pontine Islands

06/15/2026

Andrea G.

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IT

Experience to frame! Mirko is a very prepared and helpful skipper, as well as a wonderful person and an excellent cook. The boat is large and equipped with every comfort and convenience. The scenery of the Pontine made everything superlative and unforgettable. SUPER RECOMMENDED!!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/15/2026

Kamil J.

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GB

Our yacht trip with Alessandro was absolutely incredible. The weekly itinerary was perfectly planned, and every place we stayed was beautiful, with just the right amount of time spent at each destination. Carlo, our host, is the sweetest person on earth. He looked after us the entire time and made us feel truly welcome. The boat was very comfortable, and we never felt like there wasn’t enough space. Alessandro is extremely patient and such a genuinely nice person—it’s impossible not to like him. This has been one of the best experiences we’ve ever had, and we would highly recommend it to anyone considering this trip.

Midweek relaxing in the Pontine Islands

06/15/2026

Emanuele S.

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IT

I would say everything perfect! Starting with the boat which is almost new, clean and efficient! Then special mention for the skipper Mirko who, in addition to being an excellent captain, is at the same time a cook, tour guide, entertainer, barman ... etc etc . super recommended holiday ! Fair winds to all !!

Dream weekend in the Pontine Islands

06/15/2026

Federico F.

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IT

Beautiful experience! Breathtaking landscapes and crystal clear sea. Stefano, an expert commander, cheered us up during the day allowing us to sail and collaborate in maneuvers, and in the evening with guitar and songs in the moonlight; Francesca, the perfect hostess, pampered us by cooking delicacies and never letting us miss anything. When we spoke to her for the first time, she immediately made us feel welcomed, and so it was. The boat is comfortable and well maintained. In addition, the luck of having met sociable and expansive people on board made everything perfect. Highly recommended

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