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!

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

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

4.8

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

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

October

Starting from

€615

Per person

5.0

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

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

One departure available

September - October

Starting from

€240

€228

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

5.0

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

4 departures available

October

Starting from

€337

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

Midweek relaxing in the Pontine Mountains

Italy: Pontine Islands

4 days - 3 nights

5 departures available

September - October

Starting from

€337

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

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Reviews - Yacht sailing holidays & skippered tours in Italy

12580 reviews

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

07/15/2025

Arianna O.

Pasquale made this holiday even more memorable and wonderful!

Life-changing experiences - Escape to the Pontine Islands

07/15/2025

Anna R.

Italy

Francesco super! Ponza and palmarola spendid. I celebrated a memorable birthday.

Weekend on Elba Island

07/15/2025

Dalgisa B.

Italy

We had a wonderful experience with a really good, competent and nice skipper, definitely to be repeated.

Long weekend among the queens of the archipelago - Elba and Capraia

07/15/2025

Laurence B.

Belgium

My partner had a terrific time on this trip - Edoardo is a knowledgeable, patient, and welcoming skipper. We also loved the beautiful scenery and the crew. The boat was perfect for a group of eight. We highly recommend a long weekend trip with Edoardo and Sailsquare.

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