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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!

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Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

5 departures available

September - October

Starting from

€1,300

€1,040

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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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

September - October

Starting from

€700

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

€550

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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4.8

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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4.7

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

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

€419

Per person

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5.0

Super!

Weekend of the Pontine Islands to discover Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€490

€441

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

3 departures available

September

Starting from

€490

€440

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

6 departures available

September - October

Starting from

€370

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€750

€675

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

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

19037 reviews

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

09/6/2026

Andrea C.

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IT

Wonderful sailing holiday! Livio is a great skipper, he always made us feel safe, sharing his knowledge and experience and allowing us to understand what was happening to the boat at every moment of navigation. The boat has its respectable age, and if it is probably less comfortable than other more recent models, it has however arrived 7 times in the Caribbean: and what latest model can boast so many Atlantic crossings? Let Livio tell us about them, who also gave us the gift of his jovial company, not to mention his pasta with sauce with olives, capers and chilli, which ignites the conversation as well as the palate! I conclude with a greeting to my travel and goliardy companions, a nice lively and cohesive group, please, see you on the mainland!!
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A week in the Aeolian Islands - 6 islands in seven days

09/6/2026

Giorgia Z.

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IT

Unforgettable experience and wonderful places, definitely worth coming back to. A group that soon found its balance. Extremely competent and passionate skipper who involved the group in decisions, offering valuable advice based on his experience of the sea and the islands. From day one he took care that the group was balanced and that everyone participated in the daily management of the activities, an approach based on respect for the rules and common sense that is fundamental in a sailing holiday. I appreciated honesty, clarity and passion, direct communication and without formalism, which brings out authenticity and maintain a collaborative atmosphere. Qualities that on a boat are worth much more than words of circumstance. See you soon [hidden], see you soon Nik!!

Sailing among the Islands of Ulysses. Stewardess on board

09/6/2026

Fabrizio D.

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IT

Overall good experience, with room for improvement Positive aspects: the places visited are very beautiful, turquoise water, suggestive bays and pretty villages. Hansel and Léonore are very kind, they go out of their way to try to offer guests a nice holiday, their motto is: "you don't have to think about anything, just relax and have fun, we will take care of the rest". The meals are prepared directly by Hansel, which is unusual on a sailing boat, and we didn't have to think about that either. Léonore at the helm has great control of the boat. Hansel allowed me to sleep outside on the deck as I had requested, and even arranged a mattress and sheet for me to be more comfortable. Negative aspects: the boat is big, but it was designed to do round-the-world regattas, it is not a boat designed to take a vacation. It has been a bit readapted to accommodate people, but it does not have the classic sofa seating in the cockpit, the kitchen is really tiny, it does not have an awning designed to protect from the sun. And when you are in the middle of the sea in the middle of the day with the sun at its peak, you can feel it. Hansel did his best to set up sheets and sheets that certainly helped, but obviously they do not have the same effectiveness and in fact one of these was torn by the wind and we had to replace it, or in any case every time they must be removed and put back on. In the description of the boat it is written that there are 3 bathrooms and 3 cabins and that the boat accommodates up to 6 guests. It is true, but a cabin and a bathroom are reserved for Hansel and Léonore, so for the 6 guests there are in fact 2 bathrooms and only 2 cabins available, so 2 guests do not have a cabin, they have to stay in the dinette. In addition, the boat needs objective maintenance. In addition to a repainting of the deck, the bathrooms both have problems. When using the stern bath, every time the flush pump is activated it is necessary to turn around and pivot with the foot, otherwise the entire toilet bowl is lifted with the pump itself; If you want to open the window, the Plexiglas detaches from the frame. In the forward bathroom the door does not close, so you are forced to use it holding the door closed from the inside with one hand; moreover, the valve does not work well and even when you set it on the outlet it takes in waste water. The SUP has various patches and is always a bit deflated, perhaps it would be appropriate to change it. The tender would also need a leak check: one evening we had used it to go ashore all together but, seeing it deflated, on the way back we preferred to split into two groups and make two turns to avoid risks. In conclusion, the experience was overall positive, Hansel and Léonore are very nice, the places are very nice, but in light of the characteristics of the boat and its state of maintenance I don't know if I would repeat it.
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North Corsica & Tuscan Archipelago: we love to travel a lot

09/6/2026

Mirjam A.

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IT

Marco has a very well maintained boat and is a fantastic scipper: kind, very social, a lot of experience, he has a lot to tell, funny, determined, he leaves room for the needs of the group, very ready when you need special help as in my case of the accident I had during the trip. Traveling with him was wonderful for the whole group!

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