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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

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

3 departures available

July - August

Starting from

€390

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

4 departures available

August - October

€650

Per person

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5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

2 departures available

August

€649

Per person

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5.0

Super!

Cruise for Singles from Sanremo to Saint-Tropez

France: French Riviera and Porquerolles

8 days - 7 nights

One departure available

August

€750

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

3 departures available

September

€200

Per person

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5.0

Super!

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€690

€613

Per person

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4.7

Whale watching cruise with WWF guide between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

One departure available

July - August

€946

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

One departure available

July - August

€890

€680

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!

Week in the north of Corsica, via Capraia - in company

Italy: Tuscany

7 days - 6 nights

One departure available

August

€890

Per person

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4.7

Kornati: the pearl of Croatia

Croatia: Kornati Islands

6 days - 7 nights

3 departures available

August

Starting from

€800

€760

Per person

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5.0

Super!

Vento di Sicilia: from the Aeolian Islands to Trapani

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€920

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

18154 reviews

Weekend among the most beautiful coves of Elba

07/21/2026

marco c.

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IT

A nice crew in unique places!
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Sailing holiday in the turquoise blue waters of Corsica

07/21/2026

Laura P.

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IT

Beautiful itinerary. A week of freedom in a dream sea. The gorgeous weather and lovely travel companions made my vacation unforgettable!

Long weekend in the Pontine Islands between Ponza and Palmarola

07/21/2026

Valeria T.

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IT

Vincenzo very helpful and professional person, we had a really good time! Highly recommended

Weekend on a Sailing Boat in the Magical Gulf of Poets

07/21/2026

Novella C.

-

IT

A nice experience with fantastic skipper and crew!

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