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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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4.0

European Offshore Mile Builder - Leg 5: St Tropez to Malta

France: French Riviera and Porquerolles

6 days - 6 nights

One departure available

October

€550

Per person

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5.0

Unspoilt Balearic Islands for max 4 guests: Mallorca and/or Menorca

Spain: The Balearic Islands

6 days - 6 nights

3 departures available

September - October

€950

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September - October

€680

Per person

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5.0

New

Cruise to the Golden Islands via the capes and bay of St Tropez

France: French Riviera and Porquerolles

5 days - 4 nights

27 departures available

February - October

Starting from

€595

Per person

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€350

Per person

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New

Sailing Week Sardinia and Corsica

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

October

€600

Per person

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4.5

Weekend on a sailing boat in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€380

€350

Per person

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4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

June

€625

Per person

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5.0

New

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

€590

Per person

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Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

€890

Per person

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4.8

Let's sail in relaxation on Lake Garda - All Inclusive

Italy: Lake Garda

1 day - 0 nights

9 departures available

September - October

€150

Per person

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New

Premium

All inclusive sailing cruise on Dufour 48 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€1,645

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

19176 reviews

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We have known the Aeolian Islands for 20 years, live them with us!

09/21/2026

Daniela C.

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IT

We visited magnificent and unique places, saw breathtaking sunsets, hidden coves, listened to stories of volcanoes, rocks and bubbles in the sea. All magical! Pasquale is a competent and attentive captain, and also an easy-going and fun person with the aim of making the crew live an unforgettable experience. Super holiday, to try!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/21/2026

federico b.

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IT

Beautiful holiday with a crew far beyond my expectations!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

09/21/2026

Maxime M.

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LU

Very good week spent in the Aeolian Islands. I recommend.
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In the blue of Capri and the infinity of the Amalfi Coast

09/20/2026

Iolanda F.

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IT

A beautiful experience

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