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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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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

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!

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

Starting from

€490

€440

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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4.8

Super!

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

Italy: Tuscany

2 days - 2 nights

6 departures available

September - October

Starting from

€230

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?

The world's largest marketplace for sailing holidays

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.

Find out before you book who's waiting for you on board

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

19013 reviews

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Sailing week in the Tuscan Archipelago

09/4/2026

Beatrice M.

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CH

How many laughs, when well-being! We spent a week sailing around Elba in the company of Paolo. The boat is a gem and Paolo is an experienced skipper; He took care of everything leaving us the freedom to enjoy the experience. In addition to his professional skill he is also an interesting and nice person. We left in 4, and on the boat we met a third couple with whom we immediately integrated. And with 7 total people on the boat we found our harmony without ever feeling cramped. There are very precise rules that must be followed, ask Paolo as soon as you embark and if you follow them everything will be fine haha We spent a very special week made up of many baths in a beautiful sea, many peaceful roadsteads, many chats, lots of laughter and a record amount of beers! If you want to live a real experience and not just a holiday, it is the right boat for you :) p.s Paolo we will see you again soon!

Pontine and Flegree on a comfortable 15 meters: an adventure in the Mediterranean

09/3/2026

Martina P.

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IT

A truly unforgettable experience! Not only for the location. The skipper was just amazing: always attentive and helpful with all of us. Thanks to his great expertise, he was able to manage wind and sea perfectly, giving us breathtaking stops and coves in total safety and relaxation.
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Egadi Sail & Relax: the archipelago to experience

09/3/2026

Leandro D.

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IT

A truly unforgettable sailing holiday! A beautiful experience, made even more special by Paolo's professionalism and sympathy. A prepared, competent person who is always attentive to everyone's needs, capable of transmitting confidence and at the same time creating a relaxed and pleasant atmosphere. A special mention also to his qualities as a cook, he prepared typical dishes of Sicilian cuisine in a truly impeccable way. Between sea, sunsets, good food and lots of tranquility, it was a holiday that I would absolutely do again. Highly recommended for those who want to experience the sea in an authentic way, with a skipper who really makes the difference.

7 days of sailing between beautiful Croatian islands and crystal clear waters

09/3/2026

Domenico F.

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IT

A very special holiday! Emilio is a skipper with a great deal of experience, but above all a calm, patient person with a huge passion for sailing. It was nice to see him involved in trying to make us experience the sea to the fullest. He gave me valuable advice to steer the boat leaving me the helm to practice and he was very happy to let me do it, correcting me and patiently explaining everything he could help me improve. Something that I really appreciated. In addition, Emilio is an open, nice and helpful person. During the holiday he was much more than a skipper: it was like having another friend on board with whom to share days, laughter, swimming and beautiful bays of Croatia. He faced every situation with tranquility, always finding the right solution and trying to satisfy us in our requests, especially when we wanted to discover new bays or simply stop for a swim. It is rare to find a skipper who can convey so much experience and passion without ever making it a burden on the crew. A great experience, which I would definitely do again. Emilio super recommended! ⛵️

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