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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!

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

Italy: Aeolian Islands

6 days - 7 nights

7 departures available

June - September

Starting from

€583

€525

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

4 departures available

July - September

Starting from

€650

Per person

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4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

5 departures available

July - August

Starting from

€1,052

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

5 departures available

July - August

Starting from

€850

€765

Per person

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4.9

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

4 departures available

July - August

Starting from

€410

€369

Per person

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New

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

Italy: Aegadian islands

7 days - 7 nights

11 departures available

June - September

Starting from

€650

€585

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

3 departures available

July - August

€800

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

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5.0

Super!

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

10 departures available

July - October

€1,250

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

6 departures available

June - August

Starting from

€900

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

June - July

Starting from

€350

Per person

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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

Why book a holiday with Sailsquare?

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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

17695 reviews

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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

Weekend among the most beautiful coves of Elba

06/1/2026

Francesca C.

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IT

I had never had a multi-day experience on a boat, let alone on a sailboat, but I couldn't imagine a better experience than the one Marco and Carmen offered me. The [hidden] is comfortable and equipped and Marco and Carmen make it a home for the time of the experience, managing to create cohesion and participation in the group. On the [hidden] you are a crew, you learn, you collaborate and you get to know each other. The itinerary is beautiful, with crystal clear water and incredible views. I saw dolphins for the first time up close, very close. I saw fish and birds whose names I knew and for the first time I slept lulled by the waves. I really spent three beautiful days, with a nice crew that immediately, thanks above all to the energy transmitted by Carmen and Marco, cohesive and collaborated for the success of the trip. So what can I say, fair winds! I really think I will make it again and I will certainly recommend it to everyone!
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Traveling and Dreaming in the Gulf of Poets - All inclusive

06/1/2026

Maria Giovanna D.

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IT

We spent a weekend on a sailing boat with the skipper Giorgio and Francesca, two really wonderful, welcoming and professional people. Unfortunately, our holiday was abruptly interrupted by a domestic emergency that forced us to return early. In a moment of great stress for us, the skipper and his wife showed a rare empathy and flexibility: they immediately took action to reorganize and concentrate the itinerary, allowing us to still enjoy a taste of the holiday before the forced return. In addition to the beauty of the sea, we will take with us the memory of their great kindness and humanity. Highly recommended, we hope to be back soon to finish the trip!

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