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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

Weekend in Tuscany between Argentario and Giglio Island

Italy: Tuscany

3 days - 2 nights

2 departures available

October - November

€280

Per person

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5.0

Let's discover Portofino, Santa Margherita and Sestri Levante together

Italy: Liguria

2 days - 2 nights

One departure available

October - November

€430

Per person

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4.5

Wild Corsica: The Magic of a Boat Trip

France: Corsica

7 days - 7 nights

4 departures available

July - August

Starting from

€1,000

Per person

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4.8

Thailand: a dream to discover while sailing

Thailand: Phuket, Krabi and Phi Phi Islands

14 days - 14 nights

One departure available

January

€2,100

Per person

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4.0

European Mile Builder - Leg 2: Gibraltar to Las Palmas

Atlantic islands: Canary Islands

6 days - 6 nights

One departure available

November

€660

Per person

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4.9

Skiathos, Skopelos, Alonissos: The Sporades as you've never seen them before.

Greece: Sporades

6 days - 6 nights

19 departures available

May - September

Starting from

€700

Per person

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5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

One departure available

October

€215

Per person

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4.4

From Martinique to Guadeloupe riding the trade winds

Caribbean: Guadeloupe

10 days - 10 nights

One departure available

February

€1,250

€1,125

Per person

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4.7

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

11 departures available

June - August

Starting from

€660

Per person

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4.9

Life Changing Experiences - Week in the Pontine Islands with photographer on board

Italy: Pontine Islands

6 days - 6 nights

4 departures available

July - August

Starting from

€1,037

Per person

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5.0

Unspoilt Balearic Islands for max 4 guests: Mallorca and/or Menorca

Spain: The Balearic Islands

6 days - 6 nights

14 departures available

June - September

Starting from

€1,132

€906

Per person

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4.2

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

20 departures available

May - October

Starting from

€780

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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