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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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4.5

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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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

July - August

Starting from

€900

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

€950

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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4.8

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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4.8

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

4 departures available

August - September

Starting from

€900

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

18090 reviews

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

07/16/2026

Carlotta P.

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IT

Wonderful experience! Joshua is an attentive, cautious, discreet and very kind skipper. We visited the north of Corsica and loved it. Joshua took us to different beaches and all really beautiful. Good winds!!
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The North Dodecanese from Samos on a magnificent 15-meter boat

07/16/2026

Francesca T.

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IT

What a great experience! Fabio and Irene welcome you in their beautiful boat, making you feel immediately at ease. Expert guides of the Greek islands, take you to the most fascinating bays and places. Fabio, a captain with long experience, always makes you feel safe; Irene is an ideal travel companion. A holiday suitable for everyone, even those less used to sailing.
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Magnificent weekend of approach to sailing on the island of Elba

07/16/2026

Alfredo M.

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IT

Nice experience, too bad the little wind for navigation but the important thing is to have been well in excellent company. Thank you Sandro for always indulging us and making us safe! Fair winds!
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2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

07/16/2026

Vincenzo T.

-

IT

Weekend spent relaxing and having fun, we found a beautiful sea and thanks to Fabrizio's advice we fully enjoyed the boat and discovered beautiful places to swim safely with my family. It was definitely a wonderful experience.

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