475

experiences

4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,180

€1,080

Per person

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

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

July - August

Starting from

€900

Per person

4.5

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

4.7

Marmaglia mini-flotilla: discovering the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,140

€950

Per person

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

July - September

Starting from

€600

€570

Per person

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

€1,200

€1,080

Per person

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

10 departures available

August - October

Starting from

€590

Per person

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

4.6

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,110

€999

Per person

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

4.8

Super!

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

Italy: Tuscany

6 days - 7 nights

5 departures available

July - September

Starting from

€900

Per person

Why book a holiday with Sailsquare?

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

18070 reviews

Gulf of Poets

07/14/2026

Robin H.

We had an unforgettable sailing trip! It was an incredibly beautiful experience that we would do again at any time. Giovanni was incredibly warm, attentive and made sure we felt comfortable the whole time. Due to his open and friendly manner, we felt at home on the ship from the first moment. The atmosphere on board was relaxed, the landscape fantastic and the entire trip was simply perfectly organized. Thank you very much for this special experience – we can heartily recommend the sailing trip with Giovanni!

Weekend at the Pontine Islands

07/14/2026

Roberta S.

Perfect experience!! Mirko super professional and experienced!! Grade 💯 !! Highly recommended!!

Let's dream of the Tremiti Islands with a magical weekend on a sailing boat

07/14/2026

Simona B.

Pierluca is the perfect skipper Competent and safe on the boat and a helpful and kind person. A holiday with him is absolutely recommended

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

07/14/2026

Stefano M.

Riccardo is a wonderful person, he fully infuses all his innate passion for the sea, nature and sailing. Excellent teacher, if interested he allows you to participate in the maneuvers of the boat explaining each step perfectly. Wonderful proposed itinerary, excellent cook who manages to satisfy all the dietary needs of his guests. Helpful and with excellent organizational skills.

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