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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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3.0

Magical Pontine: full sail to discover the archipelago

Italy: Pontine Islands

3 days - 3 nights

3 departures available

August - September

Starting from

€499

€449

Per person

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5.0

Super!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

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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4.9

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

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4.8

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

€750

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

18483 reviews

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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

08/14/2026

Gian Luca P.

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IT

Week under the sign of the sun together with a dynamic and efficient group, authoritative skipper, of extreme experience and awareness in sailing safely. Sometimes not very malleable in the decisions, and in comparison with the crew, but a good dose of empathy, persuasion, on the part of all, every goal, desire, need was achieved, thus crowning a wonderful week of magnificent places and healthy fun. Recommended. Gian Luca .
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Midweek sailing trip: two days at sea in Alassio

08/13/2026

Alvaro B.

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IT

skipper Daniele with hospitable sailing experience Very nice and comfortable boat, great decision to sleep in the air-conditioned harbor A tip: for lunch on the boat I recommend agreeing on the menu beforehand otherwise you run the risk of having two identical lunches For the rest it was a really good experience

From Milos to Mykonos by sail, with skipper and on-board kitchen

08/13/2026

Aurora G.

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IT

It was the first experience on a boat... unique and spectacular! Annalisa and Emanuel were able to make us feel immediately at ease. Both, experienced and close-knit sailors, emanate an immense passion for what they do, able to transmit it to all their companions. Two sunny, kind, helpful and knowledgeable people who take you to discover fantastic and exclusive places; deserted beaches and islands, far from the chaos, where it is possible to admire all the beauty of the Greek islands both during the day and during the night with breathtaking starry skies. The boat is well organized, allowing you to move freely and safely even in small spaces. Moreover, Annalisa and Emanuel are also fantastic cooks, capable of preparing exquisite delicacies with local flavors and in great abundance! Also thanks to our travel companions, we can say that we embarked as perfect strangers and then disembarked feeling part of a group of friends. Thank you very much Emanuel and Annalisa for this unforgettable experience... See you soon!
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Two days at the Tremiti Marine Protected Area

08/13/2026

Anna M.

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IT

The boat and the service could be improved.... The tremors are much more than what we have seen, the sail is something else. High cost to experience. Skipper too apprehensive and not very empathetic puts you a little anxious puts you in awe and you don't enjoy your holiday Despite some very welcome gestures of courtesy, the feeling of unease prevailed. Would not recommend

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