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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!

Vento di Sicilia: from the Aeolian Islands to Trapani

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€920

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

One departure available

August

€949

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

7 departures available

August - November

Starting from

€500

€348

Per person

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4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

3 departures available

August - September

Starting from

€1,010

Per person

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5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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4.8

Super!

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

6 departures available

July - September

Starting from

€900

€855

Per person

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5.0

Super!

Relaxing holiday on the Côte d'Azur

France: French Riviera and Porquerolles

7 days - 7 nights

One departure available

August

€790

Per person

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5.0

Super!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - September

Starting from

€716

Per person

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5.0

Super!

ONE WAY Marina River - Porto Vecchio

France: Corsica

3 days - 3 nights

One departure available

August

€290

Per person

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4.4

L'Île de Beauté: sailing in Corsica with night return

France: Corsica

6 days - 7 nights

One departure available

August

€749

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

18162 reviews

Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea

07/22/2026

chiara a.

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IT

I had contacted the skipper beforehand to warn him that I did not eat fish and he had told me that there were no problems. It was not made WhatApp group before and no one was asked for preferences on breakfast, food, alcohol etc etc. We found ourselves with a galley made without sharing with a charge of 320 of wine, spirits well hidden in the shopping at the supermarket and about 500 euros of fish. I have never been offered any alternative but an egg omelette (with 50 euros spent on eggs) and twice a participant friend of the skipper made me a sauce with great controversy because the skipper imposed himself as a cook denying us to be able to cook. When I represented my need, I was literally pilloried and forced to eat salad that others ate as a side dish after succulent fish dishes. Now I'm wondering if I could get a refund??!! I had already used your platform and I had found it well, this is the reason why I used it again. I represent that we did not have the skipper indicated but there was a switch with his father Andrea who imposed the presence of his partner for two days (I do not know if he contributed to the galley). criticized me continuously because I did not eat fish and in general everyone for everything and in particular those who did not drink as much as he did. The whole group had difficulty communicating with the latter and in the last few days the situation has worsened. If you want further details write to me

Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/22/2026

Francesca C.

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IT

It was an unforgettable experience, perfect from every point of view. The skipper is impeccable, an excellent cook and knows the sea and the Pontine islands perfectly. He is very nice and a person of heart. It is a trip that I recommend to anyone, even those who are at their first experience on a boat, like me. In addition, the places are magnificent and you will love them. Super recommended 😻

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

07/22/2026

Giulio A.

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GB

Dario made us live a unique experience and an unforgettable holiday. The Aeolian Islands are a wonderful place, but surely sailing with a person with so much experience made the holiday even more unforgettable. Dario is a very prepared captain, very professional but also welcoming and helpful. His boat is spotless and is maintained with a very high standard of cleanliness throughout the holiday. Dario was able to adapt the navigation and choices according to our needs and characteristics, and this was greatly appreciated. In addition, among Dario's many qualities I would certainly include his culinary skills: his prawns and pasta are difficult to forget! Dario's big heart can also be seen in the way he takes children to heart and gives them unforgettable experiences. We will never forget this holiday. Thank you again for everything you have allowed us to experience!

Ponza and Palmarola: three days of pure relaxation

07/22/2026

Marco Q.

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IT

I think with Alessio you could only have the best as a skipper and as a connoisseur of the destination, a reliable, professional person and makes a group of people feel good by putting them at ease. Graxie of everything

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