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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

13 departures available

June - October

Starting from

€570

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August

€890

Per person

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4.6

Long weekend between Ponza and Palmarola: adventure at the Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

Per person

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4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

39 departures available

January - December

Starting from

€300

€270

Per person

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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

5 departures available

June - September

Starting from

€999

€949

Per person

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4.6

Different flotilla in Ionian Greece: nature, new friends and fun

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

Starting from

€874

€699

Per person

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4.6

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

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - October

Starting from

€650

€585

Per person

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5.0

Super!

Weekend at the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

3 departures available

June - July

Starting from

€290

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

6 departures available

June - September

Starting from

€650

€585

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

9 departures available

June - September

Starting from

€490

€466

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

Per person

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5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

12 departures available

June - September

Starting from

€790

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

17697 reviews

Cast off for a week at sea, a thousand ways to experience it!

06/2/2026

Fabienne H.

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BE

An unforgettable week on a sailboat! It was my very first sailing experience and I couldn't have asked for anything better. From the beginning, Alex, our skipper, has listened to our desires, expectations and needs, while adapting to our pace. Her enthusiasm, sense of adventure and good humour made this week particularly enjoyable. He knows how to share his passion with simplicity: we even had the opportunity to learn some navigation techniques and participate in the maneuvers, which made the experience even more fun. Sailing with the wind provides an incredible feeling of freedom, far from everyday life. Between the beautiful landscapes, the moments of relaxation and the small adventures at sea, each day was unique. I leave with a head full of memories and the desire to do it again. I recommend this experience 100% to anyone who dreams of discovering sailing, whether for the first time or for sailing enthusiasts. Roxane

Weekend among the most beautiful coves of Elba

06/2/2026

Annalisa D.

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IT

It was a beautiful experience. Marco and Carmen guided us and accompanied us on a wonderful journey. The luck of meeting a group of beautiful people made everything much easier and even the small difficulties were overcome with ease. This time I think I can really say...... FAIR WINDS TO ALL!!!!
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Gulf of Poets

06/2/2026

Flavia B.

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IT

Giovanni is the most beautiful discovery of this trip. After so many bad experiences, finally a person attentive to the needs of the crew, reserved but at the same time open and welcoming. Thanks to him we discovered magnificent coves, stories and magical places. We will definitely be back!
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Weekend among the most beautiful coves of Elba

06/2/2026

Gianmario B.

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IT

We spent the weekend with two professional, attentive and caring people towards guests. Carmen and Marco are people who enter into symbiosis right away, giving full availability to make you feel at ease and as if you have always known them. Boat in excellent condition, nothing is missing, you obviously need a spirit of adaptation not being in your bathroom at home. The relationship that is created during the experience with all the guests is also beautiful, in this experience we met wonderful people. We recommend everyone and Fair Winds

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