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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!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€350

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€410

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

€849

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

5 departures available

July - October

Starting from

€600

€540

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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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

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5.0

Super!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

2 departures available

July - September

€740

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

5 departures available

August - October

€650

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€441

Per person

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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

Per person

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5.0

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€700

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

17893 reviews

Sailing in the turquoise waters between northern Sardinia and southern Corsica

06/28/2026

Fabio B.

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IT

A true skipper!! Very professional. On a boat with Alessandro you feel very safe and calm. He has the sensitivity to understand what your interests are. Always look for the best route to the best destination which is the one that will never disappoint your expectations, in fact exceeds them. The beauty of the sea always depends on the weather and crowding conditions, Alessandro helps you to fully enjoy what you expect. And it surprises you with what you can't even imagine because it knows all the coves and beaches of the trip. Let's not forget Matteo, her second, a very kind guy who was always ready and caring, an athlete and biologist nutritionist, great competence, with whom we spent evenings chatting very pleasantly. and collecting very useful and interesting suggestions. A spectacular holiday. To be repeated. Word of a traveler!!!
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Egadi mon amour: seven days to fall in love, be amazed and relax.

06/28/2026

Marco N.

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IT

An unforgettable week in the wonderful Egadi Islands! The boat, [hidden], was comfortable and well organized, but the real added value was our skipper Giuseppe. Professional, knowledgeable and always attentive to safety, he managed to create a relaxed and fun atmosphere, making us feel comfortable from day one. He was able to take us to spectacular bays, away from the crowds whenever possible, sharing curiosities and tips that made the trip even more special. Always available, patient and with a smile, he was able to find the right balance between organization and freedom, allowing us to experience the sea in total serenity. It was an authentic experience, full of emotions, breathtaking views and moments that we will carry with us for a long time. We recommend this holiday to anyone who loves the sea and wants to experience the Egadi Islands in the most beautiful way possible. A heartfelt thank you to our skipper Giuseppe, for making this week truly perfect! Thanks also to Sara and Piero for the pleasant company. Lorena and Marco
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Sporades Experience: Freedom, Turquoise Sea and Greek Magic

06/28/2026

Raffaele S.

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IT

I have taken several sailing holidays, some of them with Sailsquare. Gianfranco is certainly a man of the sea. Unfortunately, my experience was not positive. The atmosphere on board has always been very tense, linked to the fact that it makes you feel like you are an (unwanted) guest in his home. On several occasions he addressed other members of the group in a rude and rude way, if not to me. In a week he has never used the tender nor allowed anyone to use it. Finally, I did not find the economic requests transparent: on the site a sum of 50 euros is specified as a starter pack (in addition to the common fund) while the day before leaving he sent a sort of personal vademecum in which he requested a total of 500 euros from the 8 participants, as well as requesting, before returning to port, an additional 50 euros. Ultimately, beyond the economic aspect which is not very relevant to me, I did not spend a relaxing week off work but in a very heavy and negative climate. I am very respectful of others and it would be correct to receive the same... especially if they pay you.
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Trip with photographer to the Pontine - Life changing experiences

06/28/2026

Christine S.

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US

So much fun!!! We had a lovely time sailing with Francisco. Great company with absolutely beautiful views. Would highly recommend!!

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