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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

13 departures available

June - September

Starting from

€680

€590

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

20 departures available

June - October

Starting from

€590

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

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

13 departures available

June - October

Starting from

€1,050

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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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,260

€1,134

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

6 departures available

July - September

Starting from

€795

€716

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

11 departures available

June - September

Starting from

€600

€570

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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4.7

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

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

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

13 departures available

June - October

Starting from

€689

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

5 departures available

June - September

Starting from

€950

€855

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

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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

17687 reviews

Sailing in the Aegean, the sea of the Gods!

05/31/2026

James W.

-

IT

Everything about this experience was 5 star! Andrea is an incredible professional who knows how to curate the perfect tour. If given the chance, we would absolutely sail with him again!
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In the blue of Capri and the infinity of the Amalfi Coast

05/30/2026

Alessandra C.

-

IT

Beautiful experience, very pleasant crew. Gennaro really made a difference both for his experience but also for his kindness! Highly recommended!!

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

05/30/2026

Vincenzo D.

-

IT

For us it was the first experience on a sailing boat and it couldn't have gone better. In our opinion, behind the experience, there are the people: Gennaro, the skipper, was the real wild card as well as the glue of this magnificent weekend. An exquisite person. We couldn't have wished for anything better. A guy (I hope he won't be offended) with whom every chat was constructive and full of ideas. Furthermore, to end on a high note, a further point of awareness that I took home is that thanks to him and this adventure I decided to want to obtain my boat license soon. We highly recommend this lifetime experience!
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Sailing weekend in Istria

05/30/2026

Vittoria B.

-

IT

Wonderful experience! Mirco is a reliable skipper, very attentive to all aspects of safety and excellent company. The boat is spacious and is kept in perfect condition. I had never sailed in this area and it was a pleasant surprise, perfect itinerary for a weekend, we will definitely be back!

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