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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

10 departures available

July - October

Starting from

€230

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

5 departures available

June - August

Starting from

€900

€765

Per person

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5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August

€650

Per person

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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

3 departures available

July - August

Starting from

€850

€765

Per person

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4.8

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

5 departures available

July - August

Starting from

€410

€369

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€800

Per person

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4.7

Whale watching cruise with WWF guide in the Corfu archipelago

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,052

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

14 departures available

July - November

Starting from

€540

€513

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

9 departures available

July - October

Starting from

€230

Per person

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4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

2 departures available

July - August

€800

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - October

Starting from

€600

€540

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

17820 reviews

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

06/20/2026

Valentina P.

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IT

Our very first sailing experience with Luca, the skipper, was unforgettable. A week of pure relaxation, 24 hours a day at sea, nights at anchor in front of the coves and beautiful cliffs of the Island of Elba, fantastic sunsets sipping our aperitifs, the sunrise with the scent of coffee coming out of the mocha ... moments in which time stops and you finally find the true meaning of life. And what about our skipper Luca... A very kind person, helpful, affable and also discreet, always ready to fulfill any of our requests. I hope it will be the first of a long series! Fair winds to all!! Valentina and Federico
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A week sailing in the most beautiful places in the world

06/20/2026

Daniele M.

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IT

It was a great holiday! We immediately felt like family. Giusy is a magician in the kitchen and Piero was an exceptional master skipper. The games in Burraco and Farkle have reached unattainable levels of competitiveness. It is difficult to describe in a few lines the whole week spent together, but we can say that they are 2 special people.

"Nel Blu dipinto di Blu" - midweek in Ponza, Palmarola and Ventotene

06/20/2026

Fabio F.

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IT

Everything above expectations, beautiful islands, beautiful boat, exceptional captain. to be repeated absolutely.

Long weekend on a sailing boat between Capraia and Corsica

06/20/2026

Mattia V.

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IT

We were speechless, congratulations, we couldn't have ended up in better hands, great skipper, perfect welcome!' Thank you Massimo top !!!!

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