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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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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

One departure available

August - September

€1,041

Per person

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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!

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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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

30 departures available

January - December

€300

€270

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

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

18257 reviews

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

07/30/2026

Valeria M.

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IT

Antonio is a great cook! He cooked great dishes! Very nice! During meals it is nice to listen to his stories. He knows the sea very well, he is attentive and scrupulous. Recommended holiday to experience a week of relaxation in a fabulous sea!

Egadi mon amour: seven days to fall in love, be amazed and relax.

07/30/2026

raffaella s.

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IT

Giuseppe captain of excellence! He taps his experience and knowledge of the seas he sails, attentive and helpful. He conveys confidence and also a lot of love for his work, his family and for the crew. Listen carefully to all the information and advice he offers you, they are always very useful!! We spent a fantastic week, lulled by crystal clear waters, paradisiacal landscapes and lots of fun. Embark as strangers and disembark as friends!! Don't be surprised if once you get on the ground you are ready to start again: it is the [hidden] effect! Raffaella: if today I dive fearlessly it is thanks to Giuseppe!! Marco: Giuseppe? One of us! Not the Skipper but one of the group Chiara: I brought more seasickness pills than swimsuits, but with Giuseppe at the helm and his tips I didn't use a single one. Great navigation and zero drama! Federico: Giuseppe? A super captain who made me live and appreciate my first boat experience to the fullest. Federica: a huge thank you to Giuseppe for making us live this experience from A to Z... complete with a sailor's shower included in the package. Davide: Giuseppe super Skipper available and always present, he made us spend a wonderful week on a sailing boat. Tiziana: Giuseppe, with his boat [hidden], just like the moon guides you, cradles you, takes you to the stars and the three sister islands

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

07/30/2026

Giovanna F.

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IT

Beautiful first experience on a sailing boat, with a skipper attentive to the needs of his guests and scrupulous. Livio, known (for me) as "Lucio", in addition to sailing, with his infinite stories makes you fly to spaces and places of other times ... But be careful not to take away the cookies for breakfast, he could get very angry!! Joke: peaceful and very discreet person. See you soon!
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Three days wandering among the Ionian islands

07/30/2026

Nicolas G.

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CH

Wonderful stay aboard Dario and his wife's sailboat! They showed us some great anchorages in the Ionian Islands, as well as some very good authentic Greek restaurants, away from the tourist crowds. Dario and his wife are lovely and really laid back, a real pleasure to sail with. I recommend without hesitation!

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