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

5 departures available

July - September

Starting from

€650

Per person

4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

August - October

Starting from

€200

Per person

5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€935

€748

Per person

4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

4 departures available

July - September

Starting from

€1,041

€989

Per person

5.0

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - November

Starting from

€650

€585

Per person

4.7

Dolphins & Whales cruise with WWF guide – Ligurian Sea

Italy: Liguria

5 days - 6 nights

4 departures available

July - September

Starting from

€830

€789

Per person

4.7

Whale watching cruise with WWF guide between Tuscany and Northern Corse

Italy: Tuscany

6 days - 7 nights

7 departures available

July - September

Starting from

€1,041

€989

Per person

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€550

€523

Per person

4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

5 departures available

September - October

Starting from

€294

Per person

4.6

Week between the Tuscan Islands and North Corsica

Italy: Tuscany

7 days - 6 nights

6 departures available

July - September

Starting from

€600

Per person

4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€420

€399

Per person

4.7

Whale watching cruise with researcher between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

2 departures available

July - August

Starting from

€925

€879

Per person

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Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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

Reviews - Family sailing cruises yacht sailing holidays & tours in Italy

176 reviews

On board with the chef at the Egadi Islands

07/6/2025

Loredana R.

Italy

La vacanza perfetta ! Sono anni che viaggio con Sailing Square ma mai ho trovato tanta cura ed attenzione . Max è uno skipper attento e preparato . La sua cucina è a dir poco sublime , ti stupisce ad ogni pasto , Vieni svegliato da profumi sublimi ! Ogni giornata è perfettamente organizzata tra bagni in baie protette , gite in barca a Marettimo , veleggiate rilassanti , aperitivi con sottofondo musicale e serate in ristoranti tipici sapientemente suggeriti da Max . La barca è confortevole e con ampi spazi per rilassarsi anche all'ombra grazie ad un grande tendalino .. cosa si può desiderare di più??? Grazie Max

Aperitif Trip to the Gulf of Tigullio - All inclusive!

07/6/2025

alice b.

Italy

Esperienza veramente favolosa. Super consigliata!

Dolphins & Whales cruise with WWF guide – Ligurian Sea

07/6/2025

Pierluigi T.

Italy

Tutto come da programma. Sabrina e Patric professionali, disponibili, gentili e simpatici. Gruppo ok, esperienza positiva Grazie

Aperitif Trip to the Gulf of Tigullio - All inclusive!

07/5/2025

Chiara R.

Italy

Nonostante l'uscita breve uno skipper che ha voglia di condividere con i suoi ospiti il piacere di veleggiare...se ne trovano pochi ormai

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