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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

€1,260

Per person

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4.7

Flotilla Marmaglia Sun & Fun - Croatia - WOMEN SEATS ONLY - BUS INCLUDED!

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

Starting from

€1,180

€800

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,290

€1,190

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

3 departures available

August

Starting from

€920

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 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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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

August - October

Starting from

€590

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

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 - September

Starting from

€900

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

2 departures available

August - September

Starting from

€950

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

18266 reviews

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

08/1/2026

Lisa P.

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IT

We had a wonderful sailing holiday with Alessandro, his brother and Carlo and were very satisfied with the service. From the very beginning, we had great confidence in them and felt safe and in good hands at all times. The beaches, the sea and the food were fantastic. The early starts were a bit unusual at first, but in retrospect we were able to experience more. Because of the weather and sea conditions, we returned to the port a little earlier. Even though the weather did not seem particularly problematic for us, we trusted in their experience and professional assessment. The holiday was very relaxing overall. Everyone was considerate of each other, and a nice sense of community developed on the boat. You spend a lot of time together, share special moments and can really enjoy being on the sea together. The taverns were also very good and reasonably priced. Overall, it was a wonderful and special experience that we are happy to recommend.

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

08/1/2026

Paolo F.

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IT

Beautiful week on a boat to the Pontine Islands. Our skipper made us discover the most beautiful bays of Palmarola, Ponza and Ventotene, and with the tender the most evocative ravines. Antonio is a great connoisseur of the area and has enriched us with a lot of interesting historical and cultural information, and he also cooks well! The spaces on the boat are limited and you have to adapt a bit, but with the right spirit, the experience can be remarkable!
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From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

08/1/2026

Fortunato G.

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IT

I have just concluded a wonderful holiday between the Pontine and the Aeolian Islands. For me it was the first experience of long navigation and it was an unforgettable trip, especially thanks to the great professionalism and experience of Fabrizio who knows his boat in detail and is a profound connoisseur of the islands (extraordinary on the Pontine). The initial briefing was clear and gave me a sense of absolute security: I never feared for my safety at any time. He managed the weather changes with impeccable timing, always taking us to sheltered and beautiful roadsteads and coves. I really appreciated his top priority for the safety of the crew. In addition, he involved us in sailing operations, explaining the basics of charting and maneuvering. Fabrizio is very attached to his boat and cares enormously about respecting the rules of coexistence and the management of spaces. He has a very rigorous and straightforward approach to life on board. A wonderful experience that I would do again and that I recommend to anyone looking for an extremely experienced, competent skipper able to make you sail and discover wonderful corners of the sea in total tranquility.

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

08/1/2026

Piero C.

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GB

A wonderful sailing holiday in the Côte d’Azur! The destinations were absolutely beautiful and our skipper Manuel was outstanding: knowledgeable, approachable and always focused on both safety and making sure everyone had a great time. The boat itself could benefit from a few improvements which is why I’m giving four stars overall. Nevertheless, it was a memorable trip and one I’d recommend to anyone looking for a sailing adventure.

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