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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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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

September - November

Starting from

€550

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

6 departures available

September - October

Starting from

€337

Per person

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4.8

Super!

Let's discover the Aeolian Islands together in Vela

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€690

Per person

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5.0

Super!

Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece: Dodecanese

8 days - 8 nights

One departure available

September

€650

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years. - Live them with us.

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October - November

€583

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€689

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

6 departures available

September - October

Starting from

€337

Per person

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4.8

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

€750

Per person

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4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.8

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€790

€711

Per person

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4.8

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

5 departures available

September - October

Starting from

€1,100

€880

Per person

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4.7

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

3 departures available

October

€200

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17454 reviews

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Stuffed anchovies: magical weekend from Genoa

09/16/2025

Paolo R.

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Italy

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Trekking and sailing weekend on the island of Elba

09/16/2025

Fabio B.

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Italy

Ok
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Midweek relaxing in the Pontine Islands

09/15/2025

Francesco M.

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Italy

The real value of this short cruise was the skipper Mirko, a seafarer of great experience, calm and pleasant company, who accompanied us with safety and fun to the most beautiful and characteristic corners of the Pontine Islands, always beautiful and that he knows deeply.
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The Wild Flotilla: dive into the wild nature of Tuscany and Corsica

09/15/2025

Giulia P.

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Italy

Four boats, two islands, a family: a few points to sum up one of the most beautiful holidays ever. Dinners at anchor under the stars, aperitifs at sunset, naps under the sun. But also coves and wild beaches, sperm whales and unexpected "wild". On board, a lot of sharing that, from the beginning, led us to bond with each other and to make us feel, right from the start, friends since always. A unique experience to experience the sea in a memorable way.

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