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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

Super!

Thailand and the Andaman Sea

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

One departure available

December

€1,450

€1,378

Per person

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4.9

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A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

8 departures available

May - September

Starting from

€220

Per person

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4.9

Super!

2 June long weekend - Capraia and Cap Corse

Italy: Tuscany

4 days - 4 nights

One departure available

May - June

€380

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

8 departures available

July - August

Starting from

€480

€384

Per person

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4.9

Super!

Long weekend sailing in Istria between nature and history

Croatia: Istrian peninsula

3 days - 3 nights

One departure available

April - May

€360

Per person

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5.0

Super!

Dreamy Maldives by sailboat - From Malé to Kulhudhuffushi

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February

€2,650

Per person

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4.9

Super!

Week among the queens of the archipelago - Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

One departure available

August

€1,090

€872

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

Starting from

€2,400

€2,040

Per person

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5.0

Super!

Aeolian Islands and Egadi Islands in a week with chef on board

Italy: Sicily

7 days - 7 nights

One departure available

July - August

€950

Per person

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5.0

Super!

Dreamy Maldives by sailboat - From Kulhudhuffushi to Malé

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February - March

€2,650

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€400

Per person

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4.9

Super!

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

North Sea: Norway

7 days - 7 nights

One departure available

January

€1,200

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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Come and discover Guadeloupe and its archipelago: a paradise on the water

12/16/2025

Johannes T.

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Germany

That was a great, wonderful week. Many thanks to Sabine and Patrick! Best wishes Carola and Johannes
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Weekend on Elba "Only for four" for maximum comfort

11/25/2025

D. D.

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Italy

Great weekend! Impeccable welcome on Friday evening, really much appreciated. Very professional and prepared skipper (also the other crew members) - experienced hands-on in the challenging (but fun) crossing. I learned a lot (main objective - achieved). I hope to have the chance of another experience together soon.
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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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