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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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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€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

2 departures available

August - September

Starting from

€795

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

One departure available

August

€920

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

2 departures available

August - September

Starting from

€600

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

9 departures available

August - October

Starting from

€1,300

€1,040

Per person

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4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

August - October

Starting from

€590

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

2 departures available

August

Starting from

€1,100

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

7 departures available

August - October

Starting from

€570

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

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

18355 reviews

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Sailing cruise to the Pontine: wonders a stone's throw from Rome

08/4/2026

laura r.

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IT

It is certainly easier to write a positive review, anyone is sorry to speak badly. However, since these are the holidays of people who possibly do not have further free time or money to devote to another holiday, it is right that those who choose know what they cannot understand from the photos. The absence of the backrest in the cockpit seats that forces, not being able to rest the back, to constantly balance on the waves. Small sunbeds suitable for small people, The boat is very deep so inside you can feel a lot of the sea. We booked first and, according to the regulations, we would have had the right to choose the cabins. One had already been committed regardless, it would only have been transparent to communicate it to us beforehand. Sometimes even the shape makes the difference. A check was not made on the galley, the crew did not know each other so, although there was a basic list already determined, the galley was left to the taste of the first who went shopping. Perhaps we should have been put in touch in order to share the choices. However, boat holidays and holidays with strangers require a spirit of adaptation, this one requires a little more, but it is still a holiday and therefore fair winds to everyone, if you open the sails
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La Maddalena Archipelago and South Corsica

08/4/2026

Riccardo R.

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IT

Fantastic experience among the various coves and islands of the Costa Smeralda with a great captain. Very nice boat, with various shaded areas (not taken for granted on a boat), and a great experience and knowledge of the places on the part of Gian. Thanks for everything and see you next time!
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

08/4/2026

Matteo L.

-

IT

The Pontine archipelago is confirmed as an extraordinary place: spectacular bays, crystal clear waters and landscapes that alone are worth the trip. To make the experience even more pleasant was the company, made up of people passionate about the sea and united by the desire to share experiences and stories. The weather also accompanied us for most of the week, allowing us to fully enjoy the beauty of the area. That said, some aspects could have been handled better. There was no initial briefing on emergency equipment, which would have been useful even in the absence of critical situations. On-board space was rather limited for nine people and the involvement of guests in seafaring activities was minimal, with few opportunities to sail, stay at the helm or use the tender. An aspect that was felt especially among those looking for a more participatory experience in navigation. In conclusion, it was a pleasant and overall satisfying week, ideal for those who want to experience the sea in relaxation and let themselves be guided. Those who are not beginners and are looking for a more direct involvement in nautical activities may find the setting a bit limiting.
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Maddalena Archipelago, southern Corsica: wonderful Sardinia

08/4/2026

Paola Z.

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IT

Massimo was without a sailor, in the week of mine and 2 other friends, which he knew the day before leaving. For us a hostess on board is a must. Consequent discussions then clarified through the requested intervention of sailsquare. Massimo has been corrected. No hard feelings between us, Some popular destinations, others too crowded. The boat would have everything but only one person in charge of everything, he cannot make it return. Well prepared kitchen. Improved breakfasts after clarification felt. Availability of Massimo if required what in his possibilities. Crossing with very rough seas, well managed by Massimo and fun. All in all we had a good time. I hope for him that help will arrive on board. We were all good..

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