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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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4.9

Super!

Sailing adventure in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

7 days - 7 nights

7 departures available

January - November

Starting from

€1,200

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

One departure available

October

€230

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

9 departures available

June - August

Starting from

€801

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

2 departures available

October - November

€350

Per person

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4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

4 departures available

June - August

Starting from

€1,150

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

16 departures available

June - September

Starting from

€600

€540

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

9 departures available

July - September

Starting from

€700

Per person

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5.0

Super!

Week in Ponza Palmarola and Ventotene COMODI – Max 4 people

Italy: Pontine Islands

6 days - 6 nights

6 departures available

July - August

Starting from

€1,028

€874

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

13 departures available

June - September

Starting from

€641

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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4.8

Super!

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

11 departures available

July - September

Starting from

€700

Per person

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5.0

Super!

Relaxing holiday on the Côte d'Azur

France: French Riviera and Porquerolles

7 days - 7 nights

9 departures available

April - August

Starting from

€540

€486

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.

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

19287 reviews

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The fantastic Saronic Islands and the surroundings of Athens

10/20/2026

Francesca A.

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IT

We spent a beautiful week together with Alessandro.Even if the weather was not the most clement, we were able to visit beautiful and characteristic places that we could never have discovered in any other way. In addition to the fantastic experience itself, it was Alessandro who made the difference: an experienced captain, a true master of life, with a wealth of stories to write a book about. We spent days between the sea, the wind and its stories, eating and drinking together as old friends. Thank you Ale, we will always carry you in our hearts with the hope of meeting again soon. Francesca and Davide

Squid Regatta

10/20/2026

Valentina M.

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IT

Wonderful weekend with participation in the squid regatta that allowed us to appreciate Francesco's skills as a captain. It was fun to get involved in conducting! [hidden] is a gem of a boat: convenient spaces, clean and comfortable.
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The fantastic Saronic Islands and the surroundings of Athens

10/20/2026

manuela c.

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IT

I had a great time on the boat with Ale, a professional, kind, helpful person who tried to please everyone (and it's not easy!) and super nice. I saw very beautiful places despite the islands being quite man-made, took nice baths in magnificent roadsteads and visited beautiful villages with even some trekking. Beautiful, solid and comfortable, the boat, suitable for any navigation, I have always felt safe. Ale also always available to cook for everyone! Experience to be done again next year in other islands. Thank you
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It's time for sun and sea!

10/19/2026

Francesco G.

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IT

A special thanks goes to Carlo, exceptional owner and skipper, super welcoming, prepared and smart. He managed to make us feel immediately at ease by transmitting his passion for the sea and guaranteeing us a stay in total relaxation and safety. Very nice, comfortable and clean boat. Highly recommended experience for anyone who wants to unplug and experience the sea in an authentic way.

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