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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

3 departures available

September - October

Starting from

€550

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

8 departures available

September - October

Starting from

€337

Per person

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4.8

Super!

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

Starting from

€690

€529

Per person

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5.0

Super!

The enchantment of the sea: the Dodecanese islands

Greece: Dodecanese

7 days - 7 nights

One departure available

September

€750

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

September - October

Starting from

€337

Per person

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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

September - November

Starting from

€650

€618

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August - September

€750

Per person

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4.9

Super!

Let's discover the Aeolian Islands together in Vela

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

€690

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

August - September

€689

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

2 departures available

September

Starting from

€750

Per person

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5.0

Super!

Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece: Dodecanese

8 days - 8 nights

One departure available

September

€650

Per person

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4.8

Super!

Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€870

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17178 reviews

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Elba, all the colors of the big blue - Stewardess on board - 3 Cab/ 3 Bathrooms

08/30/2025

Samantha P.

-

Italy

I felt like an unwanted guest; advertised boat with three bathrooms and three cabins while instead the cabins available for guests are 2 and the actual bathrooms only 1 because the other two are former closets in which a toilet and a sink to be extracted like a drawer have been installed; moreover, both 'toilets' not working from day one; We then used the only bathroom in 6, except for the last day when it too no longer worked. For the galley, made by the skipper and his partner, the indications received were not taken into account (I do not eat meat and they did not provide any alternative, if not remedied at the last moment), despite the amount paid, the food was poor both in quality and quantity as well as lacking preparation (boiling potatoes or pasta is not cooking, much less season it by opening 2 cans of tuna and a tablespoon of capers). Fabio and Angela are also good people but they are not suitable to host on their boat.
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Wild Sardinia, a cruise shared with nature

08/30/2025

Valeria I.

-

Italy

First time on a sailing boat. For me it was an authentic and exciting life experience, in contact with nature and in harmony with people, respecting the rhythms of the wind and the sea. Sardinia needs no introduction. The boat, Moana, although not wide, is welcoming, has stories to tell and inspires you to trust it. Federico is a friendly, patient and prepared skipper, who behaved cautiously when the weather was against us. A good harmony was created with the group on board. All this made my first time on a sailing boat an unforgettable experience and definitely not the last. Thank you!
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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

08/30/2025

Angela M.

-

Italy

The captain, Luca, and his second, Tommaso, accompanied us with competence, enthusiasm and professionalism to discover the bays of these beautiful places. We enjoyed the sailing (the real one!), the organization, the excellent cuisine and the atmosphere that was created with the group (top)! It was truly a pleasure to sail with you! Fair winds!
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/30/2025

Roberta C.

-

Italy

Great potential but we need a coordinator for the ashore outings and more logistical assistance for the galley

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