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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

12 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

17 departures available

June - October

Starting from

€590

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

2 departures available

August

€1,290

€1,190

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

12 departures available

June - October

Starting from

€1,150

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

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

5 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

11 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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4.7

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

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

5 departures available

June - September

Starting from

€950

€855

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

17736 reviews

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Midweek special between Capraia and Northern Corsica

06/7/2026

DANIELA C.

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IT

Thank you very much, Marco! You are an attentive, kind and always available skipper. From the first moment you manage to make everyone feel welcomed and at ease, sharing your beautiful boat with great generosity. Your experience and expertise convey safety and serenity, allowing everyone to fully enjoy every moment of navigation. The boat is perfect, spotless and equipped with every comfort. You know how to choose the best routes and spectacular destinations. Thanks also to my travel companions for the pleasant company.

Midweek special between Capraia and Northern Corsica

06/7/2026

Silvia G.

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IT

Thank you Marco, you were an excellent skipper, you told us so many interesting things, you led us safely to beautiful places.,Waking up in the morning and swimming in an emerald bay, all for us, is an unforgettable experience! Thanks also to all the travel companions who helped make this trip magical.....and thanks especially to [hidden]!

Midweek special between Capraia and Northern Corsica

06/7/2026

Samantha G.

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IT

Four unforgettable days between Capraia and North Corsica with fantastic travel companions! Marco is a perfect skipper: kind, professional, prudent, always available and caring with everyone! I hope to be able to travel with him again in the future
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Midweek special between Capraia and Northern Corsica

06/7/2026

Maurizio Z.

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IT

Beautiful experience, the skipper Marco, prepared, helpful and caring. The boat is very beautiful and well cared for and above all very clean. The tour was very nice and Marco introduced us to places and legends of the Island of Capraia and Corsica. We felt pampered and above all safe throughout the trip. Definitely to be repeated in another itinerary!

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