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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!

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!

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 getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

3 departures available

July - August

Starting from

€410

€328

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

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5.0

Super!

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

19 departures available

June - October

€1,250

Per person

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5.0

Super!

Weekend del Garda

Italy: Lake Garda

2 days - 2 nights

One departure available

May

€189

Per person

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4.9

Super!

June 2nd long weekend sailing through the Istrian seaside villages (from Lignano)

Croatia: Istrian peninsula

4 days - 4 nights

One departure available

May - June

€460

Per person

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4.9

Super!

Sailing course for beginners

Italy: Liguria

2 days - 1 night

4 departures available

January - February

Starting from

€270

Per person

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5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

One departure available

June

€69

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

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

17619 reviews

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New Year's Eve in Thailand: 10 days of magic in the Andaman Sea

01/7/2026

angelo r.

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Italy

They promised me a boat not crowded with random people, they promised me a competent skipper or at least conscious and prepared in knowing how to lead an entire crew. They promised me incredible roadsteads and dream beaches. They promised me that we would almost never go ashore and that we would wash little. In one way or another I still managed to wash myself: for the rest they were right. Left with strangers, returned with friends. Not recommended for lovers of trashy tracks, group dances, annoying drunks and Sunday skippers: because Sunday is the only day you will have to let the skipper take a nap. I would leave tomorrow.
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New Year's Eve on the French Riviera between relaxation Provençal scents and sailing

01/6/2026

Fabrizio D.

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Italy

The French Riviera in winter is an experience to try if we then add a very prepared skipper and crew of beautiful people I could not wish for more, and then the weather gave us a big hand
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Come and discover Guadeloupe and its archipelago: a paradise on the water

12/24/2025

Manfred B.

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Austria

It was a great week with Sabine and Patrick! They are very flexible and strive to accommodate every request! Every day a new adventure! Sailing, shore excursions, snorkeling......, - there is something for everyone
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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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