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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!

Long weekend of June 2 in the archipelago of La Maddalena and south of Corsica

Italy: Northern Sardinia

5 days - 4 nights

One departure available

May - June

€450

Per person

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4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

4 departures available

June - August

Starting from

€1,150

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

6 days - 6 nights

13 departures available

June - September

Starting from

€800

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

16 departures available

June - September

Starting from

€600

€540

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

9 departures available

July - September

Starting from

€700

Per person

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5.0

Super!

Week in Ponza Palmarola and Ventotene COMODI – Max 4 people

Italy: Pontine Islands

6 days - 6 nights

6 departures available

July - August

Starting from

€1,028

€874

Per person

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4.9

Super!

From Kos to Rhodes: the beautiful south Dodecanese

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - September

Starting from

€850

€808

Per person

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4.9

Super!

Route to the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person

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4.9

Super!

From Samos to Kos – Seven days sailing among the Aegean islands

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - August

€900

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

13 departures available

June - September

Starting from

€641

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

€1,300

Per person

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4.8

Super!

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

11 departures available

July - September

Starting from

€700

Per person

Why book a holiday with Sailsquare?

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

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

19291 reviews

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Feast of Santa Candida in Ventotene

11/9/2026

Gennaro A.

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IT

Pleasant holiday in an always suggestive setting. The feast of Santa Candida in Ventotene is a pleasant discovery and every year I gladly go back ...

It's time for sun and sea!

11/5/2026

francesca t.

-

IT

All very nice !! and Carlo... A very good sailor and a very kind and hospitable person !! Francesca
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Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

11/3/2026

Paolo P.

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IT

Excellent experience, boat up to expectations, skipper attentive to the safety of the crew and always available to evaluate every request of the people on board. To repeat the adventure for other destinations.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

11/3/2026

Alvise V.

-

IT

Great!

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