638

experiences

4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

21 departures available

May - October

Starting from

€590

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

14 departures available

June - September

Starting from

€680

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

12 departures available

May - September

Starting from

€1,000

€890

Per person

4.8

Super!

From Cagliari to Cannigione.. exploring the east coast of Sardinia

Italy: Southern Sardinia

6 days - 7 nights

One departure available

May

€550

Per person

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

June - September

Starting from

€550

€523

Per person

4.7

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

Italy: Tuscany

6 days - 6 nights

4 departures available

June - August

Starting from

€1,052

€999

Per person

4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

7 departures available

July - September

Starting from

€795

€716

Per person

5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

15 departures available

June - October

Starting from

€689

Per person

5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

16 departures available

May - October

Starting from

€540

Per person

5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

8 departures available

June - September

Starting from

€825

€743

Per person

4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

4 departures available

July - August

Starting from

€890

Per person

4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

16 departures available

May - October

Starting from

€650

€585

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

17654 reviews

May Day between Elba and Capraia

05/6/2026

Silvia V.

Italy

Very competent skipper, with a choice of stages always careful and well thought out to avoid possible inconveniences and please everyone. Thanks to the good weather and the favorable wind, it was the perfect combination of sailing and moments of relaxation and conviviality."

1st May: Whale watching expedition with WWF guide on an 18-meter schooner

05/5/2026

Patrizia A.

Everything was beautiful, except for the management of drinking water which seriously worried me.

Weekend in the Pontine Islands

05/5/2026

Antonella M.

Italy

We spent 3 beautiful days! Fabio is an attentive and nice skipper.

Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola

05/5/2026

Jacopo G.

Italy

Three fantastic days in the Pontine Islands together with an excellent company that was able to bond right away. Matteo is an experienced and very capable skipper who never gives up on his knowledge and is also very nice and very skilled in the kitchen! The boat is gorgeous!! Large, spacious and equipped with every possible service. Definitely highly recommended!!

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