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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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4.9

An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

6 departures available

June - September

Starting from

€750

Per person

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4.7

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€999

€949

Per person

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4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

3 departures available

July

Starting from

€390

Per person

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4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

2 departures available

August

€510

€459

Per person

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5.0

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

3 departures available

June - July

Starting from

€285

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

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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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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

June - September

€280

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

4 departures available

June - August

Starting from

€700

Per person

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4.9

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

2 departures available

August

Starting from

€1,060

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

10 departures available

June - October

Starting from

€800

€720

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.

-

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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