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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!

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

Italy: Sicily

4 days - 3 nights

One departure available

September

€345

Per person

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4.8

Super!

Squid Festival on the Island of Capraia - 2 boats in company (22 seats)!

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

Per person

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5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

October

Starting from

€950

€570

Per person

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5.0

Super!

Weekend on Elba on a 16-meter sports boat

Italy: Tuscany

2 days - 2 nights

One departure available

September

€400

Per person

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4.8

Super!

Experience the sea in October!

Italy: Tuscany

2 days - 2 nights

4 departures available

October

€200

Per person

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4.9

Super!

Two days in Elba without worries with a professional skipper

Italy: Tuscany

2 days - 2 nights

One departure available

October

€315

Per person

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€570

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

3 departures available

September - October

€370

Per person

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5.0

Super!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

6 departures available

September - November

€300

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

4 departures available

September - October

Starting from

€230

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

5 departures available

October - November

€350

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

19200 reviews

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Relaxing weekend and sailing school

09/24/2026

Giacomo G.

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IT

I can't give more than 5 stars. The Sailsquare platform responded quickly to my requests by hitting the target. Contact with Edoardo was very precise, right information at the right time. At the beginning of the course, the short theoretical briefing loaded us with notions in a couple of hours... This made us understand further techniques of life on a boat. For us it was the first time. Navigation? Wow !! Let's fly Super Edoardo!! Super recommended cruise/course! The boat has all the spaces to live comfortably, probably the weather conditions have also helped us a lot. Undoubtedly also the other guys who participated, like us, contributed a lot to make the weekend wonderful 🤩
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Feast of Santa Candida in Ventotene

09/23/2026

Andy H.

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ES

Great trip to Ventotene. The fiesta is perfectly staged and a real multi-sensorial experience. The islanders know how to have fun and spare no expense in making the party BIG. Our skipper Francesco made sure we were safe (big storm first night) and took us to great spots en route and on Ventotene, handling any complications over the weekend camly and confidently. We saw dolphins, Luna Rossa speed past us coming back to Naples and great views en route and varied September weather. 10/10 to Francesco, a lovely guy.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/23/2026

Pamela T.

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IT

It was my first boating holiday and I couldn't have imagined a better experience. Alessandro and Carlo are prepared, attentive and welcoming. Eros, the third member of the staff, an added value. A perfect triptych as a corollary of a try that speaks for itself. Two smart ideas: - travel in tandem with the boat of Andrea, Alessandro's brother - the beach game in the shoal, certainly the funniest memory as well as an excellent team-building initiative. Saying goodbye to them and putting their shoes back on was very difficult! ;)
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Amazing Pontine Islands on a sailboat with private bathrooms

09/23/2026

Fabrizio T.

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IT

A weekend on a sailing boat in the Pontine Islands with this skipper was a fantastic experience, combining safety, sympathy and excellent company. Skipper Dario faced a storm on Friday night with great professionalism and confidence, proving to be a responsible and active professional. He was always available and prepared at every moment of navigation. Enrica was also on board, a welcoming and kind presence that made the atmosphere even warmer and more familiar. The boat is nice and functional, although a little dated, but equipped with everything you need to experience the sea in comfort and safety. Highly recommended for those who want to experience the authentic sea with a highly reliable crew

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