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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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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

3 departures available

September

€200

Per person

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4.9

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

Italy: Tuscany

7 days - 6 nights

7 departures available

August - September

Starting from

€650

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

One departure available

July - August

€946

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

One departure available

July - August

€890

€680

Per person

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5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

4 departures available

August - September

€649

Per person

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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

4 departures available

July - August

Starting from

€250

Per person

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4.8

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

July - August

€900

Per person

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5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

7 departures available

July - September

Starting from

€550

€495

Per person

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4.7

Kornati: the pearl of Croatia

Croatia: Kornati Islands

6 days - 7 nights

3 departures available

August

Starting from

€800

€760

Per person

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5.0

Super!

Sailing Holiday with a Hostess Among the Wonders of Northern Sardinia

Italy: Northern Sardinia

6 days - 6 nights

6 departures available

July - September

Starting from

€1,450

Per person

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5.0

Super!

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€690

€613

Per person

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5.0

Super!

Vento di Sicilia: from the Aeolian Islands to Trapani

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€920

Per person

Why book a holiday with Sailsquare?

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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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