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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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4.8

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€962

€866

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

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

Italy: Aeolian Islands

7 days - 7 nights

18 departures available

June - October

Starting from

€690

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

€290

Per person

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5.0

Istria and Kvarner sailing – Relaxation and comfort with hostess on board

Croatia: Istrian peninsula

7 days - 7 nights

5 departures available

May - June

€1,100

Per person

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New

Sailing Week Sardinia and Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

October

€600

Per person

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4.4

L'Île de Beauté: sailing in Corsica with night return

France: Corsica

6 days - 7 nights

5 departures available

July - August

Starting from

€750

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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4.2

Discover the South of Sardinia by sailing, white beaches and tradition

Italy: Southern Sardinia

6 days - 7 nights

2 departures available

August

Starting from

€896

€806

Per person

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4.6

Enjoy: in the blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 6 nights

18 departures available

May - September

Starting from

€600

€540

Per person

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4.4

The unspoiled paradise of the BVI

Caribbean: BVI - British Virgin Islands

10 days - 10 nights

One departure available

March

€1,350

€1,147

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

19284 reviews

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It's time for sun and sea!

10/19/2026

Francesco G.

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IT

A special thanks goes to Carlo, exceptional owner and skipper, super welcoming, prepared and smart. He managed to make us feel immediately at ease by transmitting his passion for the sea and guaranteeing us a stay in total relaxation and safety. Very nice, comfortable and clean boat. Highly recommended experience for anyone who wants to unplug and experience the sea in an authentic way.
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IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper

10/19/2026

Chloe Maira G.

-

IT

fabulous hour spent with Filippo and his beloved dog NOA, professionalism, humor, good food, great sailings all the desirable

The fantastic Saronic Islands and the surroundings of Athens

10/19/2026

ASLIHAN A.

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TR

Alessandro was the best captain one could ask for. I had to leave after two nights because of a health emergency back home. He offered me a free sailing trip im April.

Magical Barcolana Weekend: the most famous regatta!

10/19/2026

LUIGI L.

-

IT

Wonderful experience with a wonderful team. Strongly suggested

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