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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!

Traveling and Dreaming in the Gulf of Poets - All inclusive

Italy: Liguria

2 days - 2 nights

One departure available

May

€360

Per person

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4.9

Super!

"Nel blu dipinto di blu" - Sailing cruise in Northern Corsica

Italy: Tuscany

7 days - 7 nights

10 departures available

June - September

Starting from

€680

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

June

€360

Per person

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5.0

Super!

Thailand and the Andaman Sea

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

3 departures available

December

€1,450

€1,378

Per person

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4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

16 departures available

May - September

Starting from

€430

€409

Per person

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5.0

Super!

Maldive da sogno in barca a vela - Da Malé a Kulhudhuffushi

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February

€2,650

Per person

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5.0

Super!

Seyschelles Islands... Welcome to paradise!

Indian Ocean: Seychelles

11 days - 11 nights

3 departures available

April - June

€2,400

€2,040

Per person

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5.0

Super!

Maldive da sogno in barca a vela - Da Kulhudhuffushi a Malé

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February - March

€2,650

€2,385

Per person

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5.0

Super!

In the Aeolian Islands with chef on board

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July

€1,000

Per person

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4.8

Super!

Pontine Blue - Midweek Escape

Italy: Pontine Islands

4 days - 3 nights

17 departures available

April - July

Starting from

€210

Per person

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4.9

Super!

On holiday with Dad to discover Elba and Capraia

Italy: Tuscany

5 days - 5 nights

4 departures available

June - September

€350

Per person

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4.8

Super!

The sea and sailing in winter, 2 days on the island of Elba

Italy: Tuscany

2 days - 1 night

6 departures available

January - December

€190

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17617 reviews

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A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

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Italy

Everything worked out great, Paolo was super helpful!!!! Advice 100%
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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/10/2025

giulia f.

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Italy

I participated in the weekend on a sailing boat organized for the Squid Festival and I couldn't ask for anything better! It was a wonderful experience, between sea, wind and excellent company. The crew was great: nice people and with a great desire to have fun. The skipper is super professional, but also helpful and attentive to let us experience sailing in a relaxed and fun way. I can't wait to get back on board for the next adventure! ⚓️🐙✨ Giulia, Eva and Martina
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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/5/2025

Marco F.

-

Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.
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LET'S GO TO TOTANI - Festival in Capria

11/5/2025

Marco D.

-

Italy

Unforgettable and fun experience, very prepared skipper who tamed a sea that was not exactly docile. The fishing competition is beautiful and suggestive.

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