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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!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

5 departures available

September - October

Starting from

€230

Per person

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4.9

Super!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

One departure available

September

€400

Per person

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4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

Per person

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4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, e Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

September

€1,150

Per person

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5.0

Super!

Pula and the enchanting Kvarner islands: special price private cruise

Croatia: Kornati Islands

6 days - 6 nights

One departure available

August

€780

Per person

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4.8

Super!

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

Italy: Tuscany

6 days - 6 nights

2 departures available

August - September

€980

Per person

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4.8

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

One departure available

September

€380

€361

Per person

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5.0

Super!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

Starting from

€312

Per person

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4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

4 departures available

August - September

€600

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

7 departures available

September - October

Starting from

€370

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

18727 reviews

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Ibiza & Formentera: an exclusive journey between sky and sea

08/23/2026

Carmen P.

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ES

Very favorable
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/23/2026

Donatella D.

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IT

Super holiday! It was my first flotilla and I didn't really know what to expect and it was one of the most beautiful holidays I have ever had. The skipper was impeccable in his job despite his young age and was also an integral part of our enjoyment. The co-skipper was able to involve us in every activity and her advice was always valuable. I met wonderful people with whom we formed a group immediately and in such an intense and spontaneous way that it seemed like years that we had known each other. The Aeolian Islands are beautiful and have a particular energy and magic, partying in these waters was amazing and liberating. Grateful for everything!
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Maddalena Archipelago, southern Corsica: wonderful Sardinia

08/23/2026

Paola C.

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GB

One of the most authentic experiences I have had on a sailboat, thanks to my travel companions, Valentina and Massimo. Relaxation, beautiful sea, wind that allowed us fun sailing, excellent food, great laughter. Massimo is a competent and reassuring captain who, thanks to his knowledge of the sea and the territory, has always found the best solutions to make us fully enjoy the beautiful Sardinian and Corsican islands. Valentina is energetic, smiling, very kind, and happy to share her knowledge as a marine biologist. Both made us feel comfortable from the first moment. Always attentive to the needs of the guests, their presence was not limited to the management of the boat and the organization of life on board: they helped to create an atmosphere of great harmony and complicity among all the participants. A perfect week that I will remember with great pleasure and that I highly recommend!
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/23/2026

Luca L.

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IT

The initiative in itself to undertake a group trip related to sailing, nature, discovering new places is positive. Too bad that from my point of view it takes only one problematic person in the group who can compromise the balance of the trip. On the other hand, fortunately, I met a unique person, the skipper Mr. Karim who was a super professional, kind and admirable person; During this experience he was always instructive and diligent towards the team. Ready to answer any questions about sailing and technicality, All this has had a very positive impact and I have excellent memories of it.

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