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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!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

28 departures available

March - October

Starting from

€460

Per person

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4.8

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

July - August

€900

Per person

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4.8

Super!

Discovering the wild Peloponnese

Greece: Peloponnese

7 days - 7 nights

One departure available

July

€880

€792

Per person

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4.8

Super!

From Kalamata to Milos: the fantastic and wild South Peloponnese

Greece: Cyclades

7 days - 7 nights

One departure available

July

€850

€765

Per person

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4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

€903

Per person

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4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

22 departures available

May - October

Starting from

€600

Per person

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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

19 departures available

May - October

Starting from

€600

€540

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

3 departures available

June

€360

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

€1,400

Per person

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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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4.8

Super!

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

12 departures available

May - October

Starting from

€272

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

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.

-

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.

-

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.

-

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.

-

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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