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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!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

7 departures available

September - October

Starting from

€230

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

€954

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

4 departures available

August - October

€650

Per person

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5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

Per person

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4.4

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

10 departures available

August - November

Starting from

€540

€513

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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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€280

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

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4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

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5.0

Super!

Pula and the enchanting Kvarner islands: special price private cruise

Croatia: Kornati Islands

6 days - 6 nights

One departure available

August

€950

Per person

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4.3

La Dolce Vita on a sailboat: discovering the Côte d'Azur

France: French Riviera and Porquerolles

7 days - 6 nights

One departure available

August

€649

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

September

€400

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

18452 reviews

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

08/11/2026

Nycla N.

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IT

Sabrina, our marine biologist, is a highly trained professional: thanks to her special empathy and ability to involve the group (adults and children) she made us live a truly unique and exciting experience by taking us by the hand into the world of cetaceans with a surprising passion. Captain Cesare, very experienced and always attentive to all of us, with his sympathy has added moments of lightness and joy that we will carry with us forever. Margot boat: beyond the mattresses (which have seen better times), I would point out an aspect that could be useful for future outings: one of the three cabins was undersized compared to the others and, being above the diesel tank, released fumes that made it unsuitable for accommodating people. For this reason, my cabin mate and I chose to sleep on deck for the duration of the trip (fortunately with favorable weather). Personally I would allocate that cabin more to storage (e.g. luggage) you would lose a cabin, but it would guarantee greater safety and comfort to the participants.
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A week sailing in the most beautiful places in the world

08/11/2026

Chiara M.

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IT

Piero and Giuseppina were unique! - Very clean boat, very well maintained; They do everything to make the whole crew feel good. - Giuse's cuisine is superb (for my birthday we even made a cake together 🤍) - Piero, too nice, a real silhouette. He was an excellent captain who shared his knowledge, making us "steer" his own boat and teaching us the world about the world of sailing. Thanks again and see you next time. EH WELL!!

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/11/2026

Ivan V.

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IT

beautiful experience and beautiful Aeolian islands, which I recommend everyone to try!! thanks to all the staff, but especially to our skipper Andrea who was impeccable. Also nice the group that formed on board the boat, we immediately entered on the same wave, lots of laughter and guaranteed fun!! what can I say.. I would do it again immediately!!

Week of sea and colors: crossing from Milos to Ios

08/11/2026

Maria Cristina T.

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IT

The boat is a gem, its skipper Alessio keeps it in perfect condition and steers it with great competence. Alessio is really nice, passionate about his work and involves the whole crew in the maneuvers. The choice of places and activities was impeccable. I would recommend everyone to sail with Alessio

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