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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!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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4.5

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€850

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!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

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5.0

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

6 departures available

August - September

Starting from

€790

Per person

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4.9

Super!

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€990

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

Starting from

€700

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September

€790

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

4 departures available

September - October

Starting from

€600

€540

Per person

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4.8

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€845

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

18376 reviews

The Island of Elba, to make you live a special experience!

08/7/2026

Carlotta T.

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IT

We spent unforgettable days. Great company, lots of aperitifs, beautiful landscapes and a special thanks goes to Livio who made us sail safely, involved in the management of the boat teaching us the tricks of the trade and pampered us with his delicacies!
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Two days at the Marine Protected Area of the Tremiti Islands

08/7/2026

Gioia F.

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BE

Great experience on all fronts. Marco was an attentive, fun skipper and always ready to pass on his knowledge and passion for the sea and the Tremiti Islands. Wonderful holiday. Super recommended.
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

08/7/2026

Manuel C.

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IT

The Pontine on an Old Style sailboat are pure magic. The skipper was impeccable: professional, attentive and able to make us experience the sea to the fullest, including delicious dishes, postcard anchorages and tender rides in the most evocative caves of Palmarola, the weather conditions did not allow sailing, but the skipper managed the navigation with professionalism, making every move safe and pleasant. Too bad that the travel company described this fantastic week with unfounded claims and criticisms. But the experience, thanks to the skipper and the places, remains truly special.

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

08/6/2026

Antonio C.

-

IT

Competent, experienced and helpful skipper. Comfortable and spacious boat. Costa Smeralda even more beautiful by boat. Unforgettable experience

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