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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!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September - October

€600

€540

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!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

7 departures available

September - October

Starting from

€230

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

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

€490

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

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4.8

Super!

COUS COUS FEST: Un Week End di Mare, Vela, Cous Cous e Musica!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

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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4.3

New

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

September - October

Starting from

€890

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

One departure available

September

€280

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

September

€790

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

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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Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

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

19004 reviews

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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.

Sardinia and Strait of Bonifacio on a 50-foot sailboat

09/2/2026

Huseyin G.

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TR

I joined the trip as a solo traveler and it was a lovely week on boat with our captain Gianluca and Italian company. The bays and coves we visited were just fantastic. This was my third time in Northern Sardinia and I just can’t get enough of it. For the first time I have seen the Corsica side (only the south, around Bonifacio) and the beaches there were equally amazing. I especially loved the lagoon between Piantarella beach and Ile Piana. You can literally walk from the beach to the nearby island in one of the most crystal clear turquoise water you can find. The planning in advance was great. The experience of our captain was clear, we did the shopping the first evening we all came together and we were ready the sail first thing in the morning. I was also lucky enough to have great Italian company who helped significantly with cooking. Thanks again, il capitano, Gianluca, and everyone else. I already look forward to my next Sardinia trip.

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