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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

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

21 departures available

May - October

Starting from

€590

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€680

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

12 departures available

May - September

Starting from

€1,000

€890

Per person

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4.8

Super!

From Cagliari to Cannigione.. exploring the east coast of Sardinia

Italy: Southern Sardinia

6 days - 7 nights

One departure available

May

€550

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

June - September

Starting from

€550

€523

Per person

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4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

4 departures available

June - August

Starting from

€1,052

€999

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

7 departures available

July - September

Starting from

€795

€716

Per person

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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

15 departures available

June - October

Starting from

€689

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

16 departures available

May - October

Starting from

€540

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

8 departures available

June - September

Starting from

€825

€743

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

4 departures available

July - August

Starting from

€890

Per person

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4.6

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

Italy: Northern Sardinia

6 days - 7 nights

16 departures available

May - October

Starting from

€650

€585

Per person

Why book a holiday with Sailsquare?

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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

17658 reviews

1st May: Whale watching expedition with WWF guide on an 18-meter schooner

05/6/2026

rosanna b.

-

Italy

I am satisfied with the knowledge that Laura has transmitted to us about cetaceans, dolphins etc. the knowledge on where and how they live on what they feed and what we humans could do if we were human, to help them live better, the explanations were very simple but effective and clear Laura is very competent in the subject. Pleasant destinations for the search for cetaceans, hearing their chatter through the headphones was very pleasant. The crew helpful, the boat a little too spartan. overall it was a good experience.
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Weekend in the Pontine Islands

05/6/2026

Emanuele A.

-

Italy

Memorable experience. Fabio is an exceptional person... nice, easy-going, and expert in navigation and all the gems of the Pontine Islands. The crew, whom I did not know, was a great discovery, and a rare harmony was immediately created, thanks to the love for the sea that naturally united everyone. Definitely to be redone! Thank you Fabio, thank you sea!
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Weekend in the Pontine Islands

05/6/2026

Antonio A.

-

Italy

EXCELLENT SKYPPER WITH GREAT EXPERIENCE OF THE PONTINE. BOAT VERY WELL MAINTAINED AND COMFORTABLE. RECOMMENDED

May 1st long weekend between Elba and Capraia - 2 boats in company

05/6/2026

Massimo A.

-

Italy

Matteo is the most knowledgeable person on sailing I have ever met, and his boat has a comfort far superior to normal charters, having 18 meters in length. Perfect organization and reliability. The tour of Elba is easy but wonderful

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