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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!

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

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

June - September

Starting from

€700

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

2 departures available

August

€1,290

€1,190

Per person

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4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,180

€1,080

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

July - October

Starting from

€590

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

11 departures available

July - October

Starting from

€1,300

€1,170

Per person

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4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€390

€351

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

9 departures available

June - September

Starting from

€600

€570

Per person

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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,260

€1,070

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

3 departures available

July - September

Starting from

€795

Per person

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4.7

Marmaglia mini-flotilla: discovering the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,140

€1,040

Per person

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4.6

Different flotilla in Ionian Greece: nature, new friends and fun

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,110

€999

Per person

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4.6

Long weekend between Ponza and Palmarola: adventure at the Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

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

17865 reviews

Weekend in the Pontine Islands between Ponza and Palmarola

06/24/2026

stefania c.

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IT

Beautiful experience... we traveled with Luca C. super prepared and nice skipper, who taught us a lot about the sea, sailing and sailing. Highly recommended experience, I will probably do it again!!!
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Tuscany and Corsica: sailing sun adventure good food energy and well-being

06/24/2026

Mariacristina M.

-

IT

Hello! Despite the postponement of the start date to the 19th for technical reasons, I would say that it could not have gone better! A wonderful experience, definitely to be repeated... Great company, top boat, even better food! I thank and hug Daniele and Mariapia for the passion, kindness and care for the hospitality of their guests, a real pampering! See you next😘 time Fair winds!!
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In the heart of the Cyclades, from Milos to Athens (Lavrio)

06/24/2026

Alessandro A.

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IT

Spectacular experience. Beautiful landscapes, meetings with spectacular people, good food. Unfortunately, due to Meltemi at winds and more knots every day, the route has been changed to avoid sailing against the wind every day, but you must always keep in mind that it can happen and that you have to adapt to the sea and the wind. Andrea Exceptional skipper, he made us feel safe throughout the trip, solved every problem that arose, suggested the best solutions to navigation problems, as well as being infinitely available to the needs of the guests.
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Discovering the EGADI Islands Between Nature, Relaxation and Fun

06/24/2026

Alberto I.

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CH

Between exploration, diving into crystal clear waters, delicious dishes prepared by our skipper and aperitifs in front of breathtaking sunsets, this week will remain in the heart! Beyond his skills as a skipper and knowledge of the area, which exceed all expectations, Davide has managed to create a very convivial, inclusive and fun atmosphere for a very friendly crew. varied. 😊 Thank you Davide for your positive energy, the passion you put into every trip and for making this experience so special. I would leave with you without any hesitation for the next adventure!

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