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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

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

6 departures available

September - October

Starting from

€370

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

€430

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

€466

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

3 departures available

September - October

€650

Per person

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4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,300

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

Starting from

€1,000

€750

Per person

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4.9

Super!

Sail to the edge of the world among the wonders of the North (cottage + sailboat)

North Sea: Norway

7 days - 7 nights

One departure available

October

€1,200

Per person

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4.9

Super!

Sailing holiday among the wonders of the Cyclades from Athens

Greece: Cyclades

6 days - 7 nights

One departure available

September - October

€835

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€980

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

One departure available

September

€250

€225

Per person

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5.0

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

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€350

Per person

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4.7

Palma de Mallorca All Inclusive on 18m Ketch

Spain: The Balearic Islands

6 days - 7 nights

2 departures available

September

€1,290

Per person

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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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

19005 reviews

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

09/3/2026

Francesca L.

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IT

Overall, I liked the experience, but I would have preferred more attention and care in the organization of travel, group moments and, above all, moments dedicated to the sea. Unfortunately, due to some organizational shortcomings on the part of the Different Sailing staff, I feel that it was not possible to fully enjoy the experience. The boat was also delivered to us late and in less than optimal condition: it was not particularly clean and in the following days we had to take care of the cleaning ourselves. As for the holiday itself, however, it was a lot of fun, especially thanks to our crew, made up of wonderful people who helped make the experience much better. However, it should also be noted that, initially, a maximum of 10 people per boat was expected, while in the end we found ourselves in 13, without having been adequately informed of the change. In my opinion, 13 people were a bit too many for the available space and this inevitably affected the comfort on board. Ultimately, I can't say that the experience was totally negative, because the group and the people I met made the holiday enjoyable. However, considering the organizational aspects and the condition of the boat, we will probably choose another company rather than Different Sailing in the future.
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Gulf of Poets

09/2/2026

Caterina G.

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IT

The itinerary is quite limited (thanks in our case also to the rough sea), so it can certainly be a good first experience on a sailing boat to experience life on board, but you should not expect to sail too much or see many different places. Price in my opinion a bit high for the proposed tour. Giovanni is however very nice, kind and helpful. Very nice and comfortable boat. Overall pleasant experience, but I don't think I would do it again.
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The perfect holiday on Europe's hottest and most glamorous island

09/2/2026

Giorgia S.

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IT

We had a wonderful week aboard [hidden], Paolo's sailboat, during our trip to Malta in August. Paolo was a fantastic skipper: professional, helpful, nice and always attentive to our needs. He made us discover beautiful corners of Malta, choosing special places every day to stop, swim and enjoy the sea. But what made this week really special was the atmosphere that Paolo managed to create on board: we immediately felt at home, we laughed a lot and we took home beautiful memories and a week that we will hardly forget. [hidden] became our home by the sea for a week and Paolo an important part of this beautiful experience. Thank you Paolo for this incredible week! We will definitely see you again aboard [hidden]! ⛵️❤️
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Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

09/2/2026

Rafaela C.

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IT

First experience on a sailing boat: a nice adventure with some ideas for improvement Since this is my first time on a sailing boat, the final balance is certainly positive. It was an enriching experience and the group turned out to be very pleasant, although there are some aspects that could make the trip even more comfortable and inclusive for the participants. Value of experience and galley management: The overall cost was a bit high compared to the services included. ( at the time of booking it must be specified that in addition to the initial expense there are other expenses, this has not been specified. For example.. fuel, water supply galley starter pack..... this is specified only once you have booked) Being at the first experience, we would have liked to have had extra support from the skipper or in any case from the organizational group at the time of the initial expense: a little advice to optimize the galley and avoid the superfluous (perhaps buying the rest gradually in the ports) would have been really useful. ( example once the excel has been filled in, the organizers with more experience than us can remove what seems extra to them ... instead of "scolding" each other because we did our own thing. Involvement in maneuvers: It is good to warn and know that it is an active holiday: even without any previous experience, you get involved and there is an absolute need to help the skipper during maneuvers and navigation, which makes you feel part of the crew but you need to be educated just in case. Group and fleet dynamics: Over half of the group already knew each other, and for those who struggle a little more to integrate or leave alone, this can create a small initial obstacle. To facilitate friendships, it would be great if the organization included more moments of sharing between the three boats, perhaps supporting them during the afternoon stops and not just the two evenings of sharing to really make the experience live as one big group. A trip that leaves a good memory and that I would do again, with the hope that these suggestions can help the organization to make the experience even more welcoming for future participants.

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