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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

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€795

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

9 departures available

August - October

Starting from

€1,300

€1,040

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - October

Starting from

€700

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

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

One departure available

August

€1,100

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

5 departures available

September - 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

One departure available

October

€220

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

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

8 departures available

August - October

Starting from

€570

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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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€750

€675

Per person

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5.0

Super!

Corsica Sailing Experience for only 4 people

France: Corsica

7 days - 6 nights

One departure available

August

€900

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

18462 reviews

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Weekend Elba or Capraia

08/11/2026

Ilaria Maria Z.

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IT

I spent two really beautiful days. Wonderful places and great company! Sebastiano the skipper was great, in everything. Really congratulations to him.
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South Sardinia - A Marine Paradise to Explore!

08/11/2026

Giulia L.

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IT

Francesco is an experienced skipper and we really appreciated that he took care of both cooking and washing the dishes after each meal. However, as far as the itinerary of the South of Sardinia and in particular the bays where we stopped is concerned, we were disappointed compared to other boat holidays. We expected more coves and bays that could only be reached by sea, while we were often moored offshore in front of beaches that were nothing special. Although we had immediately pointed out to Francesco that we expected something different, the week went all like this. Sorry to say that it doesn't seem to have been worth it, especially because of the long navigation times necessary for this itinerary.

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

08/11/2026

Anna M.

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IT

First experience on a sailing boat, it far exceeded my expectations! Emanuel & Annalisa are fantastic: they steer the boat with great safety, even when the weather conditions are not always easy due to the Meltemi and they know how to find sheltered bays where they can enjoy the wonderful Greek sea and breathtaking landscapes, far from the typical crowds of August. They cooked delicious dishes for us, making us discover and taste many local ingredients and flavors. The boat is well organized and equipped with everything you need to spend a pleasant and relaxing week. It is definitely not a holiday for everyone: it requires flexibility, a spirit of adaptation and the desire to share spaces and experiences. But once you try it, it is a type of holiday that remains in the heart. Hop on as a guest and come down as a friend! Thank you very much Annalisa & Emanuel, and fair winds!

Aeolian Islands: sun, sport, music, good food... The rest is magic!

08/11/2026

Mirella T.

It was a wonderful week. Dario is an excellent skipper, he knows how to sail, knows the sea well and respects it. You feel you can trust it with your eyes closed. What can I say about the Aeolian Islands.. Wonderful. Thank you from all of us😊

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