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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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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

8 departures available

July - November

Starting from

€500

€425

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

3 departures available

August - September

Starting from

€750

€675

Per person

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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€600

Per person

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5.0

Holiday in the Aeolian Islands: comfort, adventure and music! - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August

€1,050

Per person

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5.0

Super!

Cruise for Singles from Sanremo to Saint-Tropez

France: French Riviera and Porquerolles

8 days - 7 nights

One departure available

August

€650

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

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

5 departures available

September - October

Starting from

€275

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€1,020

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

9 departures available

July - September

Starting from

€980

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€370

Per person

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5.0

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

5 departures available

July - August

Starting from

€425

€383

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

18007 reviews

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Egadi Sail & Relax: the archipelago to experience

07/9/2026

Marica R.

For those who are looking for more than just a sailing holiday and not just a skipper-driver. Knowing how to convey one's passion for sailing, for the sea, for his land and revealing it to you slowly with respect and always with a big smile is not for everyone, and perhaps it is not for everyone. Paolo welcomed us in his boat (which he takes care of and knows in every part, even the impeller), in his lands, among friendships and acquaintances ... He shared with us more than I could have imagined and hoped for. I will return safe to continue the discovery of the Egadi and beyond. Fair winds! Ps. Not for those on a diet

Corfu between bays, taverns and myths.

07/9/2026

Loredana L.

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IT

Beautiful experience! Hansel, in addition to being a great captain, is also hospitable and attentive to every detail to make you experience a real holiday! She treated us like princesses, making us spend wonderful days in beautiful places and in total relaxation! Then I cannot fail to mention his skills as a great Chef! A truly special touch to everything was then given by our captain Leonor!!! super super super good, sweet and nice!
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Egadi Sail & Relax: the archipelago to experience

07/9/2026

Simone G.

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IT

There are trips that leave a mark that goes far beyond the beauty of the places visited. For my first experience alone, Paolo's presence was fundamental. In addition to an indisputable professionalism and an extraordinary boat, Paolo was able to convey a warmth and empathy that allowed me to experience this adventure in an authentic and profound way. It will undoubtedly be my point of reference for the future, I am happy to be able to say that this experience has given me a new and sincere Sicilian friend. This trip would not have been the same without Leonardo, Marica, Patrizia and Andrea: wonderful people who enriched every moment with their uniqueness, leaving me with a beautiful memory. It was a perfect experience in its harmony.
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Egadi Sail & Relax: the archipelago to experience

07/9/2026

Leo L.

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IT

One can only speak well of this holiday. Starting with Paolo who was very kind and super helpful since before the booking, when we asked if it was possible to change the departure and return dates. Paolo an exceptional skipper, a very capable cook, a travel companion who always makes you feel safe and at ease. It was wonderful to sail with him, he involved us all in the experience of steering his [hidden] very well kept. He made us visit beautiful corners of the archipelago, his knowledge of the places and people also allowed us to be welcomed in every place with great courtesy and also with some pluses that you only grant to friends. He was able to reassure even a travel companion at the first experience who rightly had some fears facing the sea, but in less than a day he was able to transform that fear into passion and serenity. I wouldn't change anything about the experience, apart from the duration that I didn't wish it would end so soon. I could talk about a thousand things but obviously the Egadi Islands must be discovered, not told, so if you are undecided about which skipper and boat to choose, choose Paolo and his [hidden].

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