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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

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

3 departures available

August - September

Starting from

€350

Per person

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5.0

Super!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

Per person

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5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

Per person

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€280

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€700

Per person

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4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€980

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

September

€400

Per person

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4.8

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

€750

Per person

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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

Per person

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4.7

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

11 departures available

August - November

Starting from

€700

€665

Per person

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4.6

The Island of Elba, to make you live a special experience!

Italy: Tuscany

6 days - 5 nights

One departure available

August

€700

Per person

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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

18570 reviews

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

08/17/2026

Luisa B.

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IT

Unforgettable experience, which went far beyond all expectations! Tiago and Paolo are exceptional, prepared, professional and passionate skippers. Good humor and lightness have always reigned on board, and in a very short time an atmosphere of deep and authentic friendship was created. A simply perfect holiday, to be repeated as soon as possible!

Different flotilla in Ionian Greece: nature, new friends and fun

08/17/2026

Angelo S.

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IT

Boat in poor condition. Never sailed due to the low wind, but not even a simulation was tried. Too much time lost in moving and mooring. Absence of a well-defined program and knowledge of the places in advance. Poor management of the organization towards the suppliers of the galley (no estimate but final account unavoidable). Deposit collection method not shared in advance with the organization, confusing chartering deposit collection. Extended check-in times.

Different flotilla in Ionian Greece: nature, new friends and fun

08/17/2026

Carla C.

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IT

Hello, I am writing to you about the week in flotilla in Ionian Greece from 8 to 15 August. Unfortunately, the experience we are living is quite different from what I expected reading the program and the information received before departure. One of the things that left me most perplexed is to discover only once we arrive that this is the first experience of Different Sailing in Greece and to have the feeling that different aspects of the trip, such as stops, restaurants and local organization, are verified and defined gradually with us. Before leaving, however, I had received a rather detailed program and therefore expected an experience already organized and tested in the destination. If I had known before that this was my first experience in Greece and that several aspects were still to be experienced on site, I probably would have evaluated the reservation differently. There were also several problems from the point of view of the boats. We left late due to problems related to the preparation and / or operation of the boats and during the week the malfunctions continued. On our boat, for example, the generator does not work even the refrigerator not closing well caused the food to deteriorate earlier than expected, also there were no cutlery, bowls and coffee machine and there were other technical problems; Problems also occurred on the other boats. There is also a lack of some on-board equipment and for some things we have to rely on the other boats. Another aspect that disappointed me is time management. We spent very long periods waiting in the ports and, in the last part of the holiday, we returned before 5 pm for fear of adverse weather conditions, despite the fact that we were already in the vicinity of the port. Overall, I found the time management not very efficient compared to the experience that had been proposed. Even some flotilla activities indicated before departure, such as the fluo party and the Hawaiian party, were not organized/planned as I expected from the program received. I was also struck to find in the pre-boarding documentation references to a "scheduled stop in Lipari" and the difficulties of refueling water "in the Aeolian Islands", when our trip is to the Ionian Islands. This also gave me the impression of an organization of the new destination that was not yet fully defined. Finally, the management of the galley also left me perplexed: for 10 people an expense of more than € 1,700 was incurred and I believe that this aspect is also part of the organizational criticalities encountered during the week. On the whole, I do not believe that the experience received fully corresponds to the one that was presented to me. I am well aware that part of the service has been used anyway and I am therefore not asking for a full refund. However, considering all the critical issues encountered, I consider it reasonable to ask for a refund. I would therefore ask you to consider my request and let me know how you intend to proceed. I look forward to your feedback. Sincerely, Carla Corso
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Sailing Holiday with a Hostess Among the Wonders of Northern Sardinia

08/17/2026

Ernesto T.

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IT

Mirko is a professional skipper who has always sailed. The safety, kindness, serenity and simplicity of make him an ideal skipper because he is never intrusive and always ready and available. Northern Sardinia and Corsica are magnificent but the week of August is the worst time to go for the quantity and quality of the people who move. Excellent boat.

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