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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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4.0

New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

2 departures available

October - November

€500

€348

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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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

Per person

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4.6

The Island of Elba, to make you live a special experience!

Italy: Tuscany

6 days - 5 nights

2 departures available

August

Starting from

€700

€650

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

4 departures available

August - September

Starting from

€490

Per person

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4.9

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

One departure available

September

€250

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

€1,000

Per person

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5.0

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

5 departures available

August - September

Starting from

€790

Per person

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5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,075

Per person

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4.9

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,080

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

18447 reviews

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Sailing in the magical Sardinia of the South

08/11/2026

Giulia D.

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IT

If you are looking for a sailing holiday where the sea decides, [hidden] is the right boat! Mine has been a week of splendid sailing, sometimes we literally slipped on the water, other times we went upwind, leaning over the sea feeling all the force of the wind! Waking up in the roadstead with the calm sea, greeting the day with postcard sunsets and looking at the stars lulled by the waves is the best for me! Thanks to Gianluca and Filippo for their expertise, for making us experience the sea to the fullest and for using the engine as little as possible. A warm greeting to my travel companions!

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

08/11/2026

Claudia D.

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IT

Beautiful experience! Our skipper Manuel was really kind, professional and very nice and gave us a lot of ideas to make the most of our holiday! The travel companions were perfect and we sailed in harmony and lightness as old friends. Beautiful sea and fabulous places... What more could you ask for? Thank you very much!

One Way from Rio Marina to Porto Vecchio

08/11/2026

Antonio S.

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IT

Very experienced, knowledgeable and welcoming skipper. He knows how to keep everyone's needs and desires together.

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

08/11/2026

Silvia Maria D.

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IT

Comfortable boat, very prepared skipper and assistant, super company. Too bad there wasn't so much wind

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