experiences

4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

October

Starting from

€200

Per person

4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October - November

Starting from

€530

€477

Per person

4.8

Super!

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

2 departures available

October

Starting from

€850

€808

Per person

4.9

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€751

Per person

4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

One departure available

September - October

Starting from

€260

€247

Per person

4.8

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

2 departures available

October

€590

Per person

4.7

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

October - November

Starting from

€1,455

€1,382

Per person

4.2

Stuffed anchovies: magical weekend from Genoa

Italy: Liguria

2 days - 2 nights

2 departures available

October

Starting from

€265

Per person

5.0

Super!

Experience in the Egadi Islands: A Dream on a Sailing Boat

Italy: Aegadian islands

7 days - 7 nights

3 departures available

October

Starting from

€400

€360

Per person

4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

October

Starting from

€294

Per person

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

October

Starting from

€615

Per person

5.0

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

4 departures available

October

Starting from

€337

Per person

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Reviews - Yacht sailing holidays & skippered tours in Italy

12482 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

Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

07/6/2025

Maila L.

Siamo stati a bordo con Matteo e Maria Teresa domenica scorsa ed è stata una giornata bellissima. Una fuga serena e di risate che ci serviva. Veleggiare con il solo rumore del mare e delle risate di nuovi amici è stato il valore aggiunto. La barca è bellissima e tenuta con la cura perfetta dei padroni di casa. Un grazie di cuore per l’accoglienza, l’attenzione ai dettagli e l’empatia. Maila e Davide

A week in the Aeolian Islands - 6 islands in seven days

07/6/2025

Rosario L.

Italy

Capitano e barca al massimo livello. Grande ospitalità , mi sono sentito a mio agio dall' inizio alla fine. Sintonia ottima anche con gli altri passeggeri. Grandi spaghettate ed ottimo cibo a bordo nella cornice delle Eolie che restano fra le migliori destinazioni in Mediterraneo. Capodanno alle Eolie ? speriamo di si.

Aperitif Trip to the Gulf of Tigullio - All inclusive!

07/6/2025

alice b.

Italy

Esperienza veramente favolosa. Super consigliata!

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