533

experiences

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

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

4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,180

€1,080

Per person

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

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

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

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

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

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

4.7

Marmaglia mini-flotilla: discovering the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,140

€1,040

Per person

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

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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Reviews - Sailboat holidays & skippered tours

17880 reviews

A romantic and luxurious vacation in the Aeolian Islands

06/27/2026

Anna D.

Unforgettable days on board Zadar. The owners Ram and Ronit, in addition to being experienced sailors, are attentive and pleasant hosts. They welcomed us with great sympathy and made us feel at home immediately. The boat is very beautiful, comfortable and impeccably maintained. We built the itinerary together and they met all our desires. Top also the freedom to cook fresh fish bought directly from local fishermen: an authentic experience! We will gladly come back!

Midweek getaway between Elba and Capraia

06/27/2026

Manuela C.

Exceptional skipper! organized, shrewd, serious and professional, he made the holiday an unforgettable memory! Capraia is wonderful!

4 weekdays in the Pontine Islands

06/27/2026

Kristian G.

Very positive experience, beautiful islands and really professional skipper and great connoisseur of the places, Sailsquare staff always available to solve any unforeseen event in the booking and management of the file,

Three-Day Sailing Tour to the Pontine Islands

06/26/2026

Ylenia M.

Three-day tour of the Pontine Islands with skipper Antonio Sánchez... Simply fantastic! Three days of pure relaxation, laughter and excellent food, immersed in wonderful places. Antonio welcomes you as an old friend: a humble, genuine and always available person. In addition to being an exceptional cook, he is a true sea dog who knows how to fascinate with his stories and knows the island in every corner. He is attentive to every detail and always ready to satisfy any need, qualities that really make the difference. An experience that I recommend without hesitation. See you on the next adventure... fair winds, Captain! ⛵️

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