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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

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

Greece: Ionian Islands

7 days - 7 nights

16 departures available

June - October

Starting from

€570

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

3 departures available

July - September

Starting from

€750

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

3 departures available

July - August

Starting from

€850

€765

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

9 departures available

July - October

Starting from

€230

Per person

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5.0

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

7 departures available

June - September

Starting from

€650

€585

Per person

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5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August

€650

Per person

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4.7

Whale watching cruise with WWF guide in the Corfu archipelago

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,052

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

Per person

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4.8

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

4 departures available

July - August

Starting from

€410

€369

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€800

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - October

Starting from

€600

€540

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

17806 reviews

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Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Domenico T.

This was my first boat adventure and what an adventure, starting from the boat which is much more spacious than I expected, passing to Emiliano, the skipper, who with his professionalism and sympathy explained the rudiments of navigation and finally the location, Ischia and Procida, which are a spectacle of Campania.

Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Domenico R.

Beautiful sailing experience between Naples, Ischia and Procida. Emiliano is a kind and helpful skipper who manages to make the experience special, actively involving those who want to feel part of the crew. Highly recommended!

Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Sabrina C.

I left for a weekend with "Spasso a vela" and it was an unforgettable experience. The boat is very comfortable, equipped with all possible amenities, it is very spacious, the cabins are comfortable and the 3 bathrooms on board are more than enough to feel comfortable. During our weekend we encountered slightly rough seas and a bit of wind but despite this thanks to the skipper's navigation experience, both in managing the navigation and in finding strategic points to dock, the weather conditions that were not entirely favorable did not weigh on us at all, so we fully enjoyed the beautiful landscapes and the sea. It was also super interesting to participate actively in life on board, the skipper taught us a lot of notions and involved us in the maneuvers. It is an experience that I recommend and that I will definitely return to do with "Spasso a vela".

A taste of the magnificent Island of Elba

06/17/2026

valentina t.

-

IT

We with friends at the Top! The boat very clean and welcoming, Alberto always on the piece helpful and attentive.

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