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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

8 departures available

August - October

Starting from

€1,300

€1,040

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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4.7

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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4.8

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!

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!

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!

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!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

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4.8

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

August - September

Starting from

€360

€300

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

18525 reviews

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/16/2026

Marta N.

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IT

Absolutely recommended, I would say fun with a little relaxation. I met several great people. TOP organization. A special thanks to the skippers who were part of the group from the first moment, Tiago and Paolo.

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

08/16/2026

ANDREA A.

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IT

An unforgettable life experience!! For my wife and I it was the first time ever on board a sailboat together with unknown people, a completely new experience that we approached with curiosity. To say that it went well would be an understatement: it was a real life experience, one of those that remain inside you. Much of the credit goes to Davide, a skipper who is simply unsurpassed. His professionalism and passion for the sea can be seen at all times: he took care of every single detail down to the smallest detail, making us feel safe and guiding us to discover emotions and sensations that are completely new to us. To make the trip even more special was the company on board. We shared spaces and days with wonderful people, with whom a unique harmony was immediately created and who I am sure will become friends for life. We will certainly return to sailing, but this first time with Davide will always remain an indelible memory. Highly recommended for anyone who wants to experience the sea in an authentic and profound way!
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Different flotilla in Ionian Greece: nature, new friends and fun

08/16/2026

Paolo N.

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IT

A wonderful experience, but with several critical issues to improve Overall it was certainly a wonderful experience, which allowed us to experience the sea, meet new people and share really pleasant moments. Precisely for this reason, however, I believe it is important to underline some major organizational shortcomings that have negatively affected a part of the trip and which, in my opinion, should absolutely be improved. The first concerns the complete disorganization of the evenings on land. We expected that, since it was a real flotilla made up of 5 boats, reservations would be planned and organized in advance in the clubs, so that we could all be together and experience the evenings as a single group. Instead, we often found ourselves having to organize ourselves, losing precisely that group and flotilla dimension that we expected from the trip. The excursions were also unclear and not always well organized. We would have liked to have had more opportunities to reach particularly beautiful sea areas and, above all, to live some organized experiences to enjoy the sunset from the sea, which on a sailing trip should represent one of the most beautiful moments. Another critical issue was the lack of music on the individual boats, despite the fact that we had been told that the system was working. Considering the type of trip and the spirit of the holiday, having the possibility to put music on board was an element that we expected and that would contribute a lot to the atmosphere. We also had the problem of the rowing tender, due to the engine not working. It is understandable that technical problems may occur, but it would have been important to find an alternative solution quickly, especially considering the need to move smoothly from the boat to land. Finally, and perhaps this is the thing I regretted the most, the final evening was completely unorganized. On a group trip and especially in a flotilla of 5 boats, I would have expected a final moment organized to be all together, celebrate the end of the trip and say goodbye. The lack of a real final goodbye was, in my opinion, a serious lack: after a week shared together, it would have been the least to expect a moment dedicated to closing the experience all together. In conclusion, there is certainly the memory of a beautiful experience and a holiday that could have been really fantastic, but precisely for this reason I believe that these aspects must be taken seriously into consideration. With more organization of activities, evenings and group moments, the trip could have reached a much higher level.
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Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

08/16/2026

federica c.

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CH

A unique experience, with professionals capable of transmitting knowledge, passion and actively involving. Wonderful places, perfect organization, pleasant group. Ready for more experiences 🫠

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