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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!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

7 departures available

July - September

Starting from

€1,450

Per person

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4.9

Super!

Life Changing Experiences - Week in the Pontine Islands with photographer on board

Italy: Pontine Islands

6 days - 6 nights

2 departures available

August - September

€1,100

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

One departure available

August

€949

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€950

Per person

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4.7

Amazing Pontine Islands in 4 days

Italy: Pontine Islands

4 days - 3 nights

2 departures available

July - August

Starting from

€437

Per person

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4.7

Whale watching cruise with WWF guide between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

2 departures available

July - August

Starting from

€946

Per person

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4.7

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - September

Starting from

€600

€540

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

4 departures available

July - September

Starting from

€490

€466

Per person

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4.8

Super!

Sea, scents and colors on Elba

Italy: Tuscany

3 days - 3 nights

One departure available

September

€300

Per person

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4.5

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August

Starting from

€850

Per person

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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

6 departures available

July - August

Starting from

€250

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

18046 reviews

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Unforgettable adventure in the Aeolian Islands

07/13/2026

luca t.

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IT

The destination is an excellent choice to spend a week at sea with unusual scenery. The journey to and from Palermo is not short (8h at least) but above all the return, after getting used to the boat, flows well. It is also the route where there is more chance of meeting dolphins and we have this luck with two young specimens that delighted us with couple jumps. On the boat everything worked and sometimes we enjoyed driving the boat ourselves. the skipper has all the necessary technical skills, it sins a bit "in the field of entertainment" but it is my personal opinion.

The most spectacular islands of the Cyclades: from Athens to Milos

07/13/2026

Marcella F.

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IT

It was a beautiful holiday! The places visited and the sea were simply stunning. The boat was beautiful, comfortable and equipped with everything you need to spend a week relaxing. A special thanks to Alessio, our skipper: an attentive, kind person and always available to meet our requests, helping to make the experience even more enjoyable. An experience I highly recommend!
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Experience the sea, feel the wind

07/13/2026

Rosangela L.

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IT

just returned from a holiday in the Egadi Islands. I am pleasantly satisfied! the experienced and kind skipper. I really appreciated that he spent time organizing everything in the best possible way and making the holiday that right mix of fun, relaxation and cultural experiences! thank you very much Matthew
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Sailing cruise between the Maddalena archipelago and Corsica

07/13/2026

Ilaria B.

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IT

Always beautiful places, a prepared, serious and very helpful skipper, I would even say a perfect cook! Definitely a positive and quality experience to be repeated as soon as possible. Spacious, welcoming boat, very well cared for in detail. Excellent cleanliness

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