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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!

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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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

7 departures available

August - November

Starting from

€500

€348

Per person

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5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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4.8

Super!

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

6 departures available

July - September

Starting from

€900

€855

Per person

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4.8

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

August - October

Starting from

€750

€675

Per person

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5.0

Super!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

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4.9

Super!

Sail to the edge of the world among the wonders of the North (cottage + sailboat)

North Sea: Norway

7 days - 7 nights

One departure available

October

€1,200

Per person

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4.8

Super!

Week in the north of Corsica, via Capraia - in company

Italy: Tuscany

7 days - 6 nights

One departure available

August

€890

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - September

Starting from

€716

Per person

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5.0

Super!

ONE WAY Marina River - Porto Vecchio

France: Corsica

3 days - 3 nights

One departure available

August

€290

Per person

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4.4

L'Île de Beauté: sailing in Corsica with night return

France: Corsica

6 days - 7 nights

One departure available

August

€749

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

18132 reviews

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Maddalena Archipelago, southern Corsica: wonderful Sardinia

07/20/2026

Andrea L.

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IT

Everything perfect. Great professionalism of skipper and sailor/chef.

Long weekend among the wonders of Elba and Capraia

07/20/2026

Barbara a.

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IT

It was a good experience. Marco, our skipper, was extremely helpful and patient. Although some of us were at our first experience on a boat, he tried to make everyone feel calm and at ease. I highly recommend it.
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Weekend on the island of Elba: among dolphins, enchanting bays and relaxation

07/20/2026

Federica P.

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IT

The skipper is undoubtedly experienced and knowledgeable and the boat was clean, well maintained and spacious. Unfortunately, however, the overall experience was not positive. At the time of booking we were told that we would be nine customers, but the skipper's wife was also on board, without us being notified. His presence led to the occupation of a guest cabin, forcing three people to sleep in the dinette despite having paid the same fee as the others. In addition, during the three days we were not given information on the Island of Elba, the itinerary or the places visited. On Saturday we were practically stationary in the same spot for the whole day, despite the fact that several participants had asked to visit other bays. Greater involvement of the group in decisions on the itinerary would have been appreciated. Finally, at mealtimes and for most of the day, the skipper and his wife occupied most of the common areas, forcing some customers to eat standing up or in uncomfortable conditions. Overall, their presence was rather invasive, both in space and in life on board. I recognize the professionalism of the skipper in the management of the boat, but as far as the organization and management of the experience are concerned, I do not feel like recommending him and I would not book a holiday with him again.
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Sailing weekend with skipper cook

07/20/2026

anna O.

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IT

Beautiful holiday, comfortable boat and the skipper took care of everything with great care and professionalism. Very nice villages in Istria. There are no colors of Sardinia but it is a different way of experiencing the sea.

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