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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

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€795

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

8 departures available

August - October

Starting from

€1,300

€1,040

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

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - October

Starting from

€700

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

One departure available

August

€1,100

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

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

5 departures available

September - October

Starting from

€570

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

Per person

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5.0

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

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - October

€690

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

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4.8

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

August - September

Starting from

€360

€300

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

18512 reviews

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

08/16/2026

Ilaria G.

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IT

Wonderful experience both on a human level (the WWF guide and travel companions) and on the level of knowledge transmitted. Seeing the cetaceans was a great emotion!

Vento di Sicilia: from the Aeolian Islands to Trapani

08/16/2026

Federica S.

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IT

Beautiful journey between the Aeolian Islands and Trapani, panoramic between lit and extinct volcanoes and between Tyrrhenian and Southern Sicily. Variety and well-being together 🌺
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Enjoy the Aeolian Islands with skipper and hostess

08/16/2026

Elio V.

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IT

Thanks to Mauro and Betty, their competence, professionalism, availability and sympathy we spent a wonderful holiday. Very comfortable boat and spectacular places. Top experience highly recommended!
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

08/16/2026

Alberto F.

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IT

We spent a fantastic week on board with Antonio discovering the Pontine Islands. Antonio is a very experienced seafarer, he knows every secret of this stretch of the Tyrrhenian Sea and guided us in total safety between the docks and the most spectacular and evocative coasts. We even experienced the magic of spotting a pod of dolphins up close during a boat lunch in Zannone! His real plus, however, is the management of the group. Despite being a crew of strangers, Antonio was super patient and sensitive to everyone's needs: he conveyed tranquility to those who were afraid of the sea, responded with extreme kindness to the curiosity of the youngest and was able to mediate with intelligence and irony even in the face of the most bizarre requests, preventing any possible tension. In addition to being an exceptional skipper, he is a very good cook, a man of great humanity and a born entertainer. He made us laugh and dream with his endless stories of life lived on the sea. Highly recommended!

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