+44

2035144220

Private yacht sailing holidays with skipper in Italy

Chartering a sailing boat in Italy will let you discover a new way of travelling new way of travelling in complete freedom. Choose between a catamaran or a sailing boat and embark with an experienced skipper to discover Tuscany, Sicily, Tuscany, Sicily, Sardinia and many other destinations.

110

experiences

4.8

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

3 departures available

September - October

Starting from

€950

Per person

4.8

Super!

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

Starting from

€690

€529

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

One departure available

August - September

€750

Per person

4.9

Super!

Let's discover the Aeolian Islands together in Vela

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

€690

Per person

4.6

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

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

September

Starting from

€750

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

5 departures available

September - November

€583

Per person

4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September

€901

Per person

5.0

Pontine Islands aboard a splendid 16-meter sailboat

Italy: Pontine Islands

4 days - 3 nights

2 departures available

September

Starting from

€450

Per person

4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

5 departures available

August - October

Starting from

€930

€700

Per person

4.8

Sail to the Aeolian Islands with an experienced crew on a catamaran!

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September

Starting from

€950

€760

Per person - min 2 pax

5.0

Weekend at the Pontine aboard a splendid 16-meter sailboat

Italy: Pontine Islands

3 days - 2 nights

3 departures available

September

Starting from

€420

Per person

4.7

Week between the Tuscan Islands and North Corsica

Italy: Tuscany

7 days - 6 nights

3 departures available

September

Starting from

€600

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

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

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

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

Reviews - Private yacht sailing holidays with skipper in Italy

2269 reviews

4 days in the Pontine Islands (sailing school)

08/29/2025

Valentina M.

Italy

Great experience! I had no doubts about the destination, the Pontine islands are a wonderful place. The skipper Michele is a calm and very kind person. Nothing negative to say. Wonderful experience also thanks to the group!

Sardinia and Corsica on comfortable 15-metre boat with private bathroom in cabin

08/29/2025

Giulia G.

Italy

For Alessandro and I it was the first experience on a cruise and I must say that it went far beyond expectations. The boat offers large and comfortable spaces, perfect for living life at sea to the fullest. Andrea, with the precious help of Sara, managed to take us to wonderful places that we would never have imagined being able to discover in total relaxation, even during the week of Ferragosto. An added value was also the excellent group that was created on board: a holiday remains such, but the right collaborative spirit makes the experience truly unique!

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

08/29/2025

Silvia M.

Italy

It was a wonderful week beyond expectations, shared with fantastic people ! An experience in total connection with nature. Paolo with his knowledge allowed us to fully experience every single day with spectacular sailings and to visit beautiful places. Vittorio great sailor person and excellent cook! I recommend to everyone, to do absolutely, there tournaments tomorrow but alas we go back to work 😔

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

08/29/2025

lara r.

Italy

My first sailing experience was amazing! Thanks to Stefano... An attentive, courteous, helpful and highly experienced skipper. He introduced us to wonderful places, never neglecting the safety of all of us. I will carry this day in my heart....thank you for making me live to the fullest!

Customer Support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Call us at

+44 2035144220

Read our

Contact & Support