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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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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

3 departures available

August - September

Starting from

€950

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

10 departures available

August - October

Starting from

€570

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

2 departures available

August - October

€220

Per person

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5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - October

€690

Per person

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5.0

Super!

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

6 departures available

August - November

Starting from

€500

€348

Per person

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4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€800

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

2 departures available

August - September

€1,150

€1,035

Per person

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4.4

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

France: French Riviera and Porquerolles

6 days - 7 nights

7 departures available

August - September

Starting from

€730

€657

Per person

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4.8

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€583

Per person

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4.7

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

3 departures available

July - September

Starting from

€360

€324

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

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

18249 reviews

Discover the Egadi Paradise by sailboat from San Vito Lo Capo

07/29/2026

Marta P.

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IT

The skippers were very good, professional, fun and company. Egadi is a paradise on earth, an ideal destination to make peace with the world. Super comfortable and spotless boat... If the wind decides to participate, it sails which is a fairy tale. thanks Jo! thanks Andre!

Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/29/2026

Maria Z.

Very nice experience, skipper super helpful to make us appreciate wonderful bays and beaches of the Pontine islands,
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Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

07/29/2026

Claudio A.

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IT

A sailing holiday simply fantastic! An unforgettable experience, between sea, relaxation and adventure. The skippers were very good: professional, prepared, helpful and always attentive to everyone's needs. (Very comfortable boat). They gave us beautiful moments, showing great attention to us, creating a very special atmosphere on board. Highly recommended, I can't wait to leave!
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Island of Elba and South Corsica fantastic week

07/29/2026

Alessandra G.

-

IT

Francesco was an excellent "host"! We had to revise the itinerary due to the weather conditions (little wind) but he was able to identify beautiful places without making us absolutely regret the tour that was planned! It was a fantastic experience to repeat

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