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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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4.8

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

7 departures available

August - October

Starting from

€1,300

€780

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

3 departures available

September - October

Starting from

€700

Per person

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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

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!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

4 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

4 departures available

October

€570

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

3 departures available

September

Starting from

€441

€419

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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5.0

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

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€690

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€750

€675

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

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.

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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

18856 reviews

Sardinia and Corsica on comfortable 15-metre boat with private bathroom in cabin

08/26/2026

David P.

-

FR

An exceptional experience on Andrea and Sarah's boat! A very well equipped boat; skippers who know the region like the back of their hand and who take us to the best places at the best times. In addition, they create a relaxed, serene and friendly atmosphere on their boat. We spent a week of happiness with our family with our 2 children (4 and 8 years old) and recommend with our eyes closed!
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Aeolian Islands: between sea and authentic flavours

08/26/2026

Emanuele O.

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IT

Fantastic experience, first time sailing for a week and it was very enjoyable. The charm and landscapes of the Aeolian Islands certainly make the difference. We sailed with the skipper Carlo, experienced and competent. Unfortunately, due to the low wind, we only sailed once. But this does not depend on anyone. Definitely recommended experience and that I would do again.

The Mediterranean Flotilla: Capri, Ischia, Procida and the Pontine Islands - ONLY MEN SEATS

08/26/2026

Anna M.

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IT

The experience overall was positive as a good atmosphere was created on board among the participants. However, there were several aspects that did not satisfy me and for which I do not think I will book another trip with Sailsquare, much less with the organizer LAFLOTTIGLIA.IT. First of all, I was looking for a flotilla experience, which for what was my knowledge of the term, meant a sailing cruise with a significant number of boats. My expectation was 5-6 boats, not 3. I had chosen this package because I had already had an experience with 3 boats and I was looking for something more aggregating, with greater participation. This aspect unfortunately combined with the fact that, despite some offer from the skipper to join another boat, most of the time they spent their time alone. We have also heard rumors from other participants of a misalignment between skippers that may have influenced the aggregation. Another negative aspect concerns the fact that the organizer LAFLOTTIGLIA.IT created the Whatsapp group, then disappeared. I tried to contact him by phone and via whatsapp and, despite the constant views of group chats, he did not consider it necessary to respond to one of his customers. The first night on the boat was traumatic for all the participants as it was impossible to fall asleep due to the very high presence of mosquitoes, due to the lack of disinfestation of a river near the Marina of Castellammare di Stabia. For weather reasons, we spent the first night in this marina and, since the last night in the marina (Friday evening) was scheduled in the program, we decided (all the participants of the 3 boats without exception) to find an alternative accommodation for that last night which, I repeat, was scheduled to be spent on the boat. I personally asked the organizer LAFLOTTIGLIA.IT and Sailsquare to recognize us a contribution for the night in the hotel that we paid for as we believed that the conditions offered by the organization, well aware of the situation in the marina, were not acceptable and that it was not correct to postpone the matter to a "simple presence of mosquitoes foreseeable on a sailing trip", This response, received by Sailsquare and not by the organizer as it was not reachable, was not considered acceptable as the incident was anything but ordinary. It also seemed to us a very unsmart choice, commercially speaking, reputationally, not to meet us as the conditions of the marina were certainly known to the organizer, therefore, if the organizer consciously chooses to have his passengers/travelers face this discomfort (I'm not talking about the first night but the last one that was scheduled in the program), something makes me think that he had a convenience starting from that marina. As for our skipper, I have no particular comments to make, he was a helpful and friendly person even if there were some communication problems during the holiday, specifically when we were talking about the itinerary to follow or the options available for the day / evening, which were always resolved peacefully although with tones sometimes a little too "heated" for my standards.
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Different flotilla in Ionian Greece: nature, new friends and fun

08/26/2026

Isabella C.

-

IT

The experience among the Ionian Islands was very nice, although personally I would revise the itinerary a bit, perhaps giving more space to some stops and to the discovery of different bays and places. The real difference, however, was made by them: Roberto, our skipper, and Michele, our co-skipper. Two fantastic people, competent, helpful and able to create a pleasant, spontaneous and fun atmosphere right from the start. They made us feel safe at all times and, at the same time, completely free to enjoy our holiday. Beyond their professionalism, what I take home is above all the human side and I think this already says a lot about the wonderful experience lived together. Thank you for the laughs, the moments shared and for making this holiday so special. ❤️ A holiday that I will carry in my heart especially for the people with whom I was lucky enough to share it.

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