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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!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

June - September

Starting from

€700

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

2 departures available

August

€1,290

€1,190

Per person

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4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,180

€1,080

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

July - October

Starting from

€590

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

11 departures available

July - October

Starting from

€1,300

€1,170

Per person

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4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€390

€351

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

9 departures available

June - September

Starting from

€600

€570

Per person

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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,134

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - September

Starting from

€795

Per person

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4.7

Marmaglia mini-flotilla: discovering the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,140

€1,040

Per person

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4.6

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

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,110

€999

Per person

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4.6

Long weekend between Ponza and Palmarola: adventure at the Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

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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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

17844 reviews

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Weekend at the Pontine Islands between Ponza and Palmarola

06/22/2026

Veronica C.

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IT

Unforgettable experience. 6 out of 5 to Commander Marco, a guarantee. A skipper of great professionalism, very reliable, attentive to everyone's needs. Marco was a point of reference for the crew as well as a true travel companion. It allowed us to see the most beautiful places in Ponza at the best times of the day, giving us an immemorial sunset, breathtaking views, truly unique experiences. You feel real seasickness when you disembark.

Weekend at the Pontine Islands between Ponza and Palmarola

06/22/2026

Claudia C.

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IT

Beautiful experience, Captain Marco is an extremely prepared, fun and welcoming person. The experience was wonderful. I hope to do it again in the future!
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Weekend Elba or Capraia

06/22/2026

Massimiliano Z.

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IT

⭐ 1 star A very disappointing experience and far from the expectations created by the advertised offer. We booked a weekend on a sailing boat from Friday evening to Sunday afternoon. The website indicated the possibility of agreeing with the skipper on a departure that would allow you to see the sunrise on the Island of Elba. Many of us had therefore organized our weekend and taken holidays as early as Friday just to take advantage of the whole experience. The first surprise came on Friday evening. Arriving at the port at 20:00, during a phone call with the contact person of the agency while we were still shopping for the galley, we were told in a sarcastic tone that we could have checked in as early as 17:00. Too bad that this information had not been communicated clearly nor was it apparent from the instructions received. Once we arrived on board we found out that we would not be leaving that evening. The skipper told us that he would have dinner and go to sleep because he doesn't sail at night. When we pointed out what was advertised on the site, we were told that at most we could leave at 6:30 the next morning. At that point we wondered what was the point of arriving on Friday evening and losing a night in port when we could have shown up directly on Saturday morning. The situation worsened during the phone call with the agency's contact person, who instead of listening to the legitimate comments of customers took an arrogant and provocative attitude, going so far as to answer: "With what you paid you can take it and leave". A phrase that I consider unacceptable towards people who had invested time, money and days off to participate in this experience. We later found out that the originally planned skipper was ill and that he had been replaced at the last moment by another captain. We understand perfectly well that the unexpected can happen, but this does not justify either the disorganization or the way we have been treated. On Saturday we left only around 7:15 in the morning. After a few stops in coves near Capraia we returned to the port for the night. During the evening we talked about the Sunday program and several participants expressed the desire to reach Elba, as implied by the initial proposal. Also on this occasion the skipper's response was particularly abrupt: he declared that he would sleep until 8 in the morning because he had not rested well the previous night and that we would not go to Elba. Further discussions followed, during which the skipper addressed the customers in a disrespectful manner, going so far as to complain that some asked to leave early and then go back to sleep. Frankly, an incomprehensible observation: we were there as paying customers on vacation, he was there to do his job. Another negative note concerns the SUPs advertised on the site. I asked in the WhatsApp group where they were and the contact person of the agency replied that they were bulky and that we should have requested them earlier. Even in this case, however, nowhere did it appear that a prior request was necessary. To sum up: unclear information, expectations created by the site that are not reflected in reality, services advertised but not available, approximate organization and above all an arrogant and unprofessional attitude on the part of the agency's contact person and the replacement skipper. Unforeseen events can happen to anyone. What really makes a difference is the way they are managed. In this experience there was a complete lack of attention to the customer, and this is the reason why I do not feel like recommending it.

Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/22/2026

Elisabetta M.

Breathtaking experience, fantastic landscapes and I had the pleasure of sharing all this with special people! A special thanks to Alessandro and Carlo for their availability and professionalism! A must do.

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